When my oldest daughter started to read on her own it took so much concentration. Every single word involved 120% of her attention. She’d start to sound out a word, get close and guess and then ask me because it wasn’t quite right. I’d tell her what word she was searching for and she’d go off on the next bit. About half way through her first page she was fed up, not because of the effort of reading though.

Whoa, this is a long post. Did you know that Members get it in PDF, and other eBook formats? They also get to join me for discussion on how to improve their business monthly and finally a monthly book group. You should become a member. You can also purchase Getting Unstuck on Amazon.

Sure the work was hard, but the frustrating part for her was that the story didn’t make any sense. The writing wasn’t bad and the story wasn’t over her head. It was a decent kid’s book for a 6-year-old. The problem was that with all of her attention focused on figuring out which word she was looking at, she had no attention to spare to piece the whole sentence together at once.

She couldn’t grasp the flow of the story because she was just barely getting the individual words.

This is where you start with any endeavor. The simple fact of getting the basics done is overwhelming. When I started teaching myself web development while getting my Counselling Degree I could barely get a site up and launched. It was all held together with duct tape and promises.

I couldn’t spare any time to dig into what it took to run an awesome business. I was hanging on praying it didn’t all fall apart around me. I didn’t have a client vetting process, or know how to do great client communication. This is normal. In fact, one of the reasons I suggest you work for an agency or web firm before you head out on your own is so that you can learn a bunch of the lessons while getting paid by someone else.

Then you have less skin in the game. The risk is lower. Once you’re out and running your own business, the risk is all yours. If you make a mistake, you pay the price.

I remember sitting at my screen in my early development days with no one to ask for help. I sat debugging for 8 hours and at the end of the day I still didn’t even know the right questions to ask.

I cried.

You don’t have to do that if you work for someone else to start.

Many people get stuck focusing on the craft of code, or design. They want to sit walled off all day and do that work, but running a business is much more than the specific item you’re selling. Thinking that your business is only about the code is like my 6-year-old spending all her concentration on the words in front of her, with nothing to spare for the bigger picture.

If you’re running a web development shop, or a web design shop, or a freelance writing agency, you are not actually in the business of design, code, or writing.

You’re in the business of sales. You need to know how to figure out the value that the client wants if you want to earn well.

You can’t sit and focus all the time on code like a Maker. You have Manager tasks to do that no one can do but you. I manage these two different types of tasks with The Mullet Method for Deep Work.

With The Mullet Method, I work 6 am – 9 am on Maker tasks. I focus without distraction. Then I take an hour or two off work and get back to it for another three hours where I allow some distractions to be around.

If marketing and sales and managing client relationships all sound like a terrible idea, then keep your job. Stay where you are and do your Maker work, with little worry about sales and management and hiring and billing. Not everyone is cut out to run their own business.

Don’t idealize running a business. It’s a lot of pain and hard work.

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What You Need To Learn to Run a Successful Freelance Business

You don’t have to stay stuck though. In fact, I assume you’re tired of being stuck and you’re looking to learn to do more than write code. You’re ready to stop focusing on just the design or the writing, and dig into how to run a business that earns well and leaves time for a life outside of working.

You want to start being not only a financial force at home, you want to be a great dad as well. Someone who has the time to build Lego with the kids while not being stressed the whole time about ‘work’ and how it’s going to happen.

You’re in luck then, because we’re going to cover the big areas you need to have a handle on if you want to build an amazing business.

First, we’ll dig into marketing and sales to help make sure that you have a handle on what it’s going to take to handle those well.

Second, we’ll look at what it means to run client relationships well. This is the part where you follow up with prospects and former clients to keep your pipeline full.

Third, we’ll discuss what it means to run a great client project. The tools don’t matter as much as the methods you use to approach the client and keep them in the loop.

Finally, we’ll dig into what it means to be personally productive. When you are on your own it all comes down to you. There is no other team member to jump in and pull you out of the fire. You are either productive and get the work done, or you aren’t. The only person you can blame is yourself.

Now, let’s get started with marketing and sales for the freelancer.

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Marketing and Sales for Your Freelance Business

The first place you’ll need to start is to figure out which niche you’re going to serve. I’ve already written a whole book called Finding Your Niche and Marketing which addresses the specifics, so this will be an overview of the high points you better have covered to even be playing the right game.

Why You Need to Niche

Deciding to go for a niche is scary. When you’re starting it feels like you’re going to be saying no to so many prospects that your revenue will dry up.

Your butthole tightens up so hard that it could be played as a snare drum.

I get it. When you’re starting it’s hard to say no to anyone with money because you’re trying to make it all work with duct tape and string. It’s okay to start here. I started there and I haven’t talked to anyone that didn’t. If you want to raise your rates and move out of the barely holding it together financially mindset, you need to start working into a niche.

The thing about a niche, any niche, is that it lets you start to target your marketing. If you decide that you’re going to work with rural farmers, you don’t bother with all the possibilities that market to New York business people. When you’re “for everyone” it’s much harder to make that decision about where to target your marketing.

You’re much more likely to make an inch of progress in 1000 directions and thus gain little traction.

My friend Philip specializes in helping businesses…specialize. He has often said that he’d rather have you pick a niche at random then market to everyone. He’s had clients do this and start earning way more money. They also find out that the random industry has interesting problems to solve. Far from being bored, Philip’s clients dive deeper and enjoy the work with that random niche.

While I agree with Philip that any niche is better than no niche, with a bit of work we can do next, you don’t have to have a random niche. You can be more intentional so your niche builds a freelance business you enjoy.

How to Find a Niche

Let’s start by thinking about what you like to do. What problems do you enjoy solving for clients? Do you love to dive deep into bad code and figure out why it’s terrible and what it should do being so that you can extract a stable system out of it for your client?

Do you love building a basic beautiful and functional site for small businesses?

Are you in love with eCommerce and making more sales?

Each of these is a valid option for a niche, but they’re not an ending point. While you can gain more traction by focusing on eCommerce, you still have to compete against everyone that does eCommerce for any business. It’s even better if you can look to a specific industry.

Do you have a background in farming, or compete in horse jumping? I spent a decade guiding outdoor trips, then 5 years selling canoes and kayaks. This experience puts me in a perfect position to market my eCommerce skills to the outdoor industry and become the leading choice for anyone with an outdoor shop wanting to move into online sales.

Now, it’s time to ask yourself, what provides the most value to prospects out of the things you like. It’s likely that building a basic site for someone is of less value than building them an online store, or increasing their conversions. You need to choose something to work on that has decent interest for you and high value for potential clients.

The final money question to ask yourself as you pick a niche for your beginning freelance business is, who has money to pay for your services.

It’s easy to default to “Fortune 100” companies, but the truth is that along with the high fees you can charge these companies is huge headaches. You get to charge lots because of those headaches.

Instead, think about what scale the business needs to have to pay for your services. You don’t need hundreds of clients a year to build a six-figure business. Five clients with an average project of $20k is a six-figure business. The Fortune 1-million has plenty of money for you and a much larger pool with less headaches. Deal with a niche inside that Fortune 1-million.

Building Persona’s

With your nice defined, it’s time to dig into exactly who you’ll talk to in that niche. Again, you can’t assume you’re going to talk to everyone if you want solid traction. You must pick specific people to talk to and then tailor your marketing to them.

A persona is a named ‘person’ with some basic characteristics defined that you can speak to. As I write this I’m thinking of my “Bob” persona.

Bob has been running a freelance business for a few years. He has had some success, but is ready to start taking the whole thing seriously. He needs to get better processes together around marketing and his own focus time. He’s tired of working 12 hour days. That worked when he didn’t have kids, but he does have kids now and he wants to be a great dad. Phoning it in at dinner while being stressed about the next payment is not what he ever dreamed of.

He dreamed of being around to build cool stuff with his kids. He wanted to roll around on the floor with them and take them sledding in the winter on a random Monday.

That means that as I write this and I’m stuck I can ask myself “what would Bob need to know about this so that he can be more successful.” That question clears up any content blocks right away.

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photo credit: clement127 cc

How Do You Build a Persona

If you have any experience in your niche at all, then you have some idea of the people that are around. Start there. My first personas were nothing more than a customer I’d met. I even used their name on the persona and then some bullet points about where they were in business and what the big problems they struggled with were.

Just like any niche is better than no niche, any persona is better than none.

If you’re trying to enter an entirely new market, then you need to start digging into it. Find the blogs, podcasts, forums, and Facebook Groups that serve the industry. As you do this, you’ll see a bunch of the same names pop up. Dig into them and start building your personas off these people.

Look at who they serve as customers and build your persona off your best guess for the customer they serve.

As you’re building persona’s aim for three. I have Brian, the person with a job that wants more freedom to be an awesome parent and is trying to start a freelance business. Bob, has started one and is needing to move it to a business instead of a shoestring and love endeavour. Finally Dave, has been doing 6-Figures consistently, but wants to do more either by building better systems or a team. Dave wants to be able to walk away for a few weeks and still have money coming in.

Each piece of content, each book, each podcast, each guest blog, is aimed at one of these three personas. Some content may be aimed at all three, say something on how to negotiate work and home time with their spouse.

Use Persona’s to Guide Your Content

Now, you’ve got some persona’s which means it’s time to use them in your business. While I don’t claim to be a daily blogger, it pretty much turns out that way. My aim is to have something for each persona in a week.

When I pick the content I’m writing I look at the three persona’s and shape the content to suit them. If I look at a week and only have stuff for that person that wants to run their own business, but isn’t doing it yet, then I look around for other content so that I can hit my other two persona’s. I don’t look at my site content every day. A monthly check in to make sure I’m hitting content relevant to each persona is enough.

Every single piece of content you put out should have these persona’s in mind. Every conference you speak at, should be shaped by these persona’s.

If you’re doing it all in a haphazard way, then you might hit the mark sometimes, maybe. More likely, you’ll scatter your marketing so far and wide that you never reach anyone effectively.

How to Get Your Name Out There

With your persona’s in place, it’s time to get your name out there because it’s possible that your niche has no idea you exist. In fact, it’s almost 100% guaranteed that most of your niche has no idea you exist.

Sure, some of the people in a market have considered you (and even rejected you). But most of the people in the market have never even heard of you. The market doesn’t have just one mind. Different people in the market are seeking different things. – The Dip

The first thing you’re going to have to get over is your fear of selling yourself. If you’re not selling yourself then no one is. There is no freelance god that blesses a beginning freelance business with goodness from the benevolent “awesomeness” of the universe so that it succeeds.

If your plan uses the word “hope” then you’re relying on this god, that doesn’t exist. Hope is not a strategy that’s going to get your beginning freelance business to the next level. It’s going to keep you going at the same barely hanging on level you’re currently at.

Now, let’s look at some of the specific methods you can use to get yourself out there. I’ve written about them in more detail in Finding and Marketing Your Niche, if you need to go deeper.


The first place to start is your own site, and blogging on it. This is the place that you control in the easiest manner. If you build a Facebook Group and then Facebook decides that they hate groups and are killing them, your whole following is dead.

While search engines are getting better at reading content that’s not plain words, words are what they’re best at dealing with. Blogging, and being focused in your blogging, will help you get found by your ideal clients.

Start by writing one item a week. If that sounds crazy because writing is hard, you’ll get better. Maybe you need to set aside an hour a week to write and then publish something every other week. The more high quality content you put out there, the faster you’ll see traction from it.

The more you write the faster you get. I can write upwards of 5000 words in two hours, but I have written 5 books and at least 1500 blog posts. Probably more because I have at least 3 old sites that had lots on them which no longer exist. You can get here, it’s going to take a while, but you can get here. All you have to do is start, and then publish.

Once you’ve got a handle on getting content on your site, it’s time to think about guest posting. Strategic guest posting can yield awesome returns. I had one guest post earn me over $50k in a year because people kept reading it and feeling I was the expert they needed. The next year it earned around the same. While I didn’t get paid for the guest post, it was obviously worth the investment of time.

Another great avenue for your content is Medium. I’ve found that republishing my content on Medium, and getting it in a publication, has been a huge driver of traffic to my site. If you’re scared of guest posting and the extra time commitment it may take then start by republishing your content on Medium and trying to get it into a publication.


Podcasting is another great way to get your voice out there. It can be better than blogging because podcasting is a higher trust method of communication. Podcasting is higher trust because people can hear your voice and your mannerisms and they are more likely to trust you. The closer you can get to shaking someone’s hand the better.

In fact, podcasting is so good that I’ve see amazing returns from my podcasting endeavours. Especially when I get one someone else’s podcast. It’s so good that no other method of ‘guesting’ is even in the same league.

I have noticed over the last year that it is getting harder to get on podcasts as a guest. As a podcaster and blogger, I think this is because so many of the requests to get on my site or show are terrible. They’re some generic email I’ve seen a many times. They tell me why whatever the person wants to talk about is perfect for my audience.

It almost always shows that they haven’t even listened to my show or looked at my audience or what I like to talk about with my guests. It’s marketing people trying to get their clients on podcasts.

If you want to start getting on podcasts, then start by finding the most obscure and niche shows possible.

For creators, it is typically easier to reach the smaller, better-defined group. If you reach the smaller group and wow them, there will be many opportunities to spread outward and upward. – Perennial Seller 

If you’ve got your niche defined, and some solid persona’s then you can find these podcasts. Listen to them and figure out who they love to talk to and what they love to talk about. Then armed with this information, send a personal pitch telling them why you think you might fit with their guests.

This is a much slower method than the pump and dump method where you fire off the same email to everyone, but you’re much more likely to hear yes.


As I said already, the closer you can get to shaking someone’s hand, the more trust you’re going to build. It’s far too easy to sit behind your computer screen, sending off emails, and think that you’re doing an awesome job marketing your business. The fastest way to getting clients will always be getting out and shaking hands.

Now, I’m not saying that you need to go out to every crap marketing event that’s out there. You should be picking any networking event in light of your niche and your persona’s. Only go to the ones that fit in with those two filters.

When you head out to a networking event, go in with a clear plan. If you can get your hands on the guest list, identify a few people that you want to talk to and do a bit of research on their business. Then, walk up to them and talk to them.

Introduce yourself and ask more questions about their business. They’ve been to a bunch of these events and they’re used to the terrible superficial questions, so go deeper and stand out.

These are not the only methods you can use to get your name out in your industry. They’re the ones I’ve seen my coaching clients do and have the most success with. In some cases, that’s been because the other even more effective methods like public speaking are so terrifying that you need a foundation of networking to even consider speaking in front of people.

How to Evaluate Your Marketing Channels

Now that you have some marketing channels going, it’s time to evaluate them. It’s no good to continue to spend time doing outreach when it’s not working. The only place you always keep going is with your own blog or podcast. This is your hub, and no matter how small the audience, it’s the place that you send everyone who interacts with you from your other marketing channels.

Establish Your Goal

The first thing you need to do is establish which channels are hitting your goals. Years ago when Stumbleupon was a thing I had clients asking how to get on it so they could get a bunch of traffic. At no point did I ever recommend wasting their time on Stumbleupon.

The thing with Stumbleupon was that it sent a bunch of traffic, that went away immediately. Sure the traffic numbers looked great, but no one made a purchase and few people converted to email subscribers. It was only a cost since it would use your server cycles and provide no benefit.

You need to think about which metric is the important one for you to measure. Do you want more traffic, or do you want more email subscribers? Are you targeting people to your video course? If you don’t know what metric is most important for your site, then you have no way to measure the success of the marketing channels you are using.

You’ll also need a way to identify users from the different channels. Say you’re on 4 podcasts. Two do little, one sends a bunch of users, but that fourth one sends you 10 solid leads who made a purchase. Which one is the most valuable one? Which one should you be looking at harder to see why it worked best and how to find that audience, or an audience like it again?

You can do this by providing a custom landing page for each audience or a coupon code to use with the purchase.

Which Channels are Hitting the Goals

Now that you have a way to figure out which channels are providing the best conversions on your important metrics, you need to look at the information. Not every day. Not every week. Don’t worry about it for at least six months.

You wait six months because it’s going to take you a while to get the ball rolling. If you’re on a podcast, it may not come out for 4 weeks so checking to see if it’s converting before it’s even out is a waste of your time.

When you look at your metrics you should be trying to figure out a few things. First, which mediums are converting the best? Is it podcasting, or blogging, or speaking, or…? Stick with the ones that convert the best and drop the others.

Second, which blogs or podcast convert best inside their medium. Try to identify their audiences so that you can find more people that might match up, but would listen to or read a different site. Then you can target that site and have some relevant “experience” inside the field to point to when you make a pitch to them.

There is more to marketing your business. This is a primer for those of you what are already freelancing, but need to turn it that beginning freelance business into something that supports you and the life you want to live.

There is a bunch more reading if you’re ready to dig in deep to the topic of marketing your business. If you’re ready for that, check out my reading list on Marketing Your Business.

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Managing Client Relationships in Your Freelance Business

Once you get more than a few prospects on the go, you need a way to keep following up with them. While you may think you had a great discussion and that the prospect will remember you forever, they won’t. Most prospects end up going with the freelancer they most recently came across.

Sure, you’re sort of on the list, but for every month you let go by without reaching out to them you’re further down the list.

This section is going to walk you through what it takes to get on a client’s list and stay on it.

One of the big pitfalls with businesses looking at a CRM is that they start with the tool in mind. Almost every time, the tool doesn’t matter. I use a paper notebook now, but have used a number of digital CRM tools.

The issue you run into by starting with a tool is that you don’t have a process worked out yet. Instead of developing a process for yourself that works, you outsource that hard thinking to the tool and just do what it says assuming that it will work for you.

This may bring a little bit of benefit, but you’ll gain so much more benefit by testing a process first, then looking at the tools that will fit into your process.

How To Do Amazing Prospect Follow Up with Your Freelance Business?

Let’s start with the basic rule that you should be following up more than you think. If you don’t feel a bit uncomfortable with the frequency of the follow up, then you’re not following up enough. I’m not saying that instead of every 3 months you should follow up daily, but for most cases 3 months is way too long to wait. It’s so long that you won’t even be on the prospect’s list anymore.

When a prospect first reaches out to you, you’ll need to follow up with them more often. If a prospect emails me on a Wednesday and I reply I assume I’m emailing them again on Tuesday. In fact, if I’ve emailed a prospect in a week and they’re not on my long term follow up plan yet (we’ll talk about that in a minute) then I email them on Tuesday.

Yes, I might email you on Friday and then on Tuesday to check in. If I don’t hear back from a prospect, then I’ll follow up weekly for four or five weeks. I always send them one final email that goes something like this.

Hey $prospect, hope the day is going awesome.
I wanted to touch base because I haven’t heard back from you recently. I’m going to assume that you’re no longer doing the project so I won’t bug you weekly anymore.
If that changes, let me know.
Have an awesome day!

Almost every time I send that email I get some response back. Sometimes the prospect opens the conversation back up, and I reset to the four or five week follow up scheme. Sometimes they agree that the project isn’t on the radar right now for some reason, and they give me a timeframe for when it will be on the radar again.

I write their name down for follow up in that window again.

Occasionally I hear nothing from them so I put them on my long term follow up plan.

There are a number of prospects or clients that will fall into the long term follow up schedule. The first one we’ll address is the prospect above. Assuming that nothing in the project seemed crazy, I’ll follow up with them every two months for a year. Even if I never hear back from them in the year, I still send them a check in email every two months for a year.

If I don’t hear back from them in any fashion, I drop them off my list of follow up. More often than not I do hear back in some fashion at some point. When I hear back from them I simply reset the two week counter. If they’ve indicated that they want to move forward with the project now, they go back on the weekly follow up for the four or five emails. Then they’d drop back into the long term follow up plan.

The second group of people that fall into the long term follow up strategy are awesome clients I’d love to work with again. They get an email every two months pretty much forever. Oh I’m sure that some awesome clients have dropped off my list for one reason or another, but I don’t intend for it to happen.

Over my 10-years in business, I’ve had a number of clients end up coming back for a big project because I emailed them. It’s been 5-years since we’ve had any interaction outside of my emails, and maybe the odd reply, but because I’ve been consistent they come right to me with work.

There is no one else even in the running for the work.

If you want a business that will run well and generate leads for you regularly, you need to stay on top of this follow up. I’ll say it again later, but the biggest issue I see when I talk to small business owners about their prospect and client follow up strategy, is that they don’t put aside time in their week to do it.

Make sure you put time aside.

What Should My Client Follow Up Look Like?

Now, what should your client follow up look like? First, you need to write your follow up in a way that suits you. I’m a bit looser than some, but it works for me. I use their possible issues with my terrible jokes in email as a way to filter out the prospects I don’t want to become clients.

A general email to a prospect I’m following up with on either the long term or weekly schedule would follow the format below.

Hey $prospect, hope the day is going awesome.
(Maybe insert some banter here)
I wanted to touch base to see what the status of the project is on your end. Are you ready to move forward with it? Is there something else that you’re planning on doing instead?
Do you have any questions or issues around your site that I can help on?
Have an awesome day!

That’s it, in fact the long term follow up email for great clients only has one addition to the format above, and you can see it. Since I’ve got to know them as clients over a while already I may insert some question about them and their family.

One client I have worked with off and on for 5 years is a triathlete. I always insert a question about his training. He’s also been interested in my outdoor adventures so I’ll tell him about what we’re doing and what I’m training for next. I did this for two years after our first project before he started the next one and then for three years before the last one I worked on with him.

The first project we worked on was $5k. The other two were in excess of $20k.

Yes the continual emails for five years has been worth it. I’m still emailing him every two months asking him how things are going.

Now take 30 minutes and work out your follow up process. Write down the email templates you’re going to use. If you need help with writing better emails to clients, I wrote a guide on how to do that called Effective Client Email. It covers more than just your client follow up emails though. It will give you the emails I’ve honed over 10-years to make sure that I’m weeding out the prospects I don’t want as clients.

What Should my CRM System Look Like?

You should have a prospect and client follow up process written down now, but how do you keep track of it? This section will introduce what I do for my analogue CRM system, and what you should be looking for in a digital tool.

What Does My Analogue CRM Look Like for a Freelance Business?

I’ve tried a bunch of digital tools and I keep coming back to an analogue system. If you keep track of my site, I’ll be writing a long piece about how I use an analogue productivity system for everything but client projects that require collaboration.

My analogue CRM is fairly close to a standard Bullet Journal system. When I have a prospect that needs to get a follow up, I stick their name on the monthly planning page that goes with the month.

If that means they fall out of the current month, I add their name to the future log with a date next to their name.

Beside the name I’ll put a number like 4/5 which means that this email I’m sending is the 4th email out of the five emails I send. That way I know which standard email to use when I send the communication.

For a prospect on long term follow up we drop the number of emails and a date goes there showing me when I stop emailing them. If they respond, then the date gets adjusted.

One thing to remember is that you need enough information beside that name so that you have the context required to find their email in your email application. When I used to outsource finding a prospect to a CRM, more often than not I’d have no idea who I was going to be emailing because I had barely glanced at them instead of needing to spend some brain power figuring out who this was and what we had talked about.

If it’s an awesome client on long term follow up, I just write the name down with the date so that I can find their information. Sometimes I’ve seen some extra information about them on social media which I’ll add beside their name so I can bring it up.

That’s it. It’s not fancy and it requires writing things over and over again, but I find that to be a benefit. It means that I become more familiar with the prospect as I have to expend a bit of mental energy. It also means that I only put the top prospects on the list to follow up with. I don’t bother with all the random low value people that send inquires my way until they jump the first bars in my client vetting process.

What Do I Look For in a Digital CRM for my Beginning Freelance Business?

If you’re not going with an analogue system then the place to start is your process. I’ve already said this, but you need to have a system down. You at least need to have an ‘ideal’ you’re aiming for with follow up. Then you need to look at the available tools and choose one that fits with your process.

If you don’t have a basic system ready, then stop looking and do the personal work first. Write down the problems you’re having and what you think the solutions may be.

Some good options for a digital CRM, all of which I’ve used at different times are:


I know there are many others out there, but those are the three I’ve spend at least a few months with that I found valuable. I spent the most time with Contactually at first, but found the extra inbox to track too much overhead so I stopped checking it. Then I worked with Streak which was built directly into my email. For some reason I just never fully “got” their system and while it was checked and followed up lots I still felt like it was a bunch of extra work to stay inside Streak.

Hence my analogue system.

The Biggest Pitfalls in Using a CRM in Your Freelance Business

The biggest issue when using a CRM in your freelance business is using it. Most freelancers hear about the benefits of using a CRM and then get a software recommendation for one and go with it. They use it for a few weeks and then it drops of the radar.

They’re still paying a monthly fee, but not using the CRM they picked. It’s an expense, bringing no benefit.

You won’t use your CRM well, if you don’t have time set aside for it in your week. In a standard 40 hour week, have two hours set aside for following up with prospects. Stick to those two hours. Guard them with your life, because a good follow up system is one of the keys to building a freelance business that succeeds.

A second pitfall with CRM’s and not using them is that they’re often outside of your personal productivity system and your project management system. They fall into the category of “out of site out of mind”. You forget about them.

When you’re choosing a system you must choose something that will integrate into your current productivity workflow in a manner that ensures you will use it.

I’ve chosen to use my paper planner for this. As I described, I follow a mostly Bullet Journal system and move prospect names forward in the future log or on a monthly collection depending on when I want to follow up with them. This means that I always need enough information written down to identify a prospect so I have to understand them and know them.

When I used OmniFocus I would end up with links to emails as tasks and I would use that ease of finding the conversation as a crutch. It meant I rarely understood the client and was rarely invested in moving forward with them. They were simply a name that came up that needed a reply. I’d end up reading through a bunch of email again every time so that I had some context.

By moving to an entirely paper system I must understand the client better. I must decided if they’re worth following up with because it’s a pain to continue to move them forward in the system. I can’t simply bump a date forward, making a promise on my future time, I must evaluate their chances of becoming a paying client as I write down their information again.

This system has resulted in a much smaller list of people that I consider prospects and put time into following up with. My win rate on those prospects is much higher though so it’s a net positive.

You can go deeper on Managing Client Relationships with my resource page.

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photo credit: clement127 cc

Project Management For A Beginning Freelance Business

The worst way to manage a project is via email. If there is more than a single task to get done, never manage a project in email. Email is almost always only a list of what others think is important for you to do in a week. It rarely matches up with what is actually important for your week.

The answer to “What is the ONE Thing I can do today that will make the rest of my business easier or irrelevant” is almost never contained in your inbox.

By moving your current projects out into a trusted system that’s not email, and that’s not your personal productivity system, you get to filter your incoming requests. You not longer see a client, who has a current agreement with you, and a prospect, who you have no obligation to, in the same interface.

Prospects have no sway on your time. They’re someone that might maybe have something you’re interested in doing if it’s perfect.

What Process Should You Use for Project Management?

You’ve taken the first step and your projects are no longer being managed in your inbox, but what system do you use?

Do you go old-school and stick with a waterfall method?

Do you get right “up with the times” and go for Scrum or Agile?

Does it matter which method you use?

I’m going to fall on the side of saying that it doesn’t matter so much what method you use. They all have benefits, and drawbacks. I use something close to Agile. I work in short sprints with clients on a fairly well defined set of tasks and we ship them.

Regardless of which methodology you adopt, there are a few thing that you need to get right if you want to ship winning projects.

Project Success Page

The first task that should go in your project management system with a client is for them. You should be giving them a link to your project success page with the instructions that they read it and then resolve the task. What…you don’t have a project success page? Well let’s talk about what that is.

First, the whole goal of the page is to communicate information to your client so that they can help you have a successful project. It’s not about berating them, it’s about giving them the information they need.

Many clients will have never seen a page like this. They’ll realize that they make projects harder, and the never knew it. It’s likely that whoever they worked with just made comments about it behind their back instead of addressing the issues like an adult.

In your project success page include any information the client will need to have a winning project. Inform them what a good task looks like. That a task which includes three different action items is one that will probably have something missed.

Tell them not to email you, and make sure you provide another link to whichever project management software you use.

Have them decide on the single point of contact, and any other people that need to be in the project management system. The fewer the better, and there always needs to be one person on their end that is responsible for making sure their team gets stuff done.

You can look at my Project Success Page if you need to see one in action. One I added this, and asked clients to read it, my problems in project management went way down.

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photo credit: clement127 cc

Get Something Up As Fast As Possible

Next, get something up for your client to see as fast as possible. When I’m building a WordPress theme, I’ll have as much of the homepage as possible done as fast as possible. Usually within a day or two.

One of the biggest fears that clients have is that you’re going to take their deposits and then flake out. It’s happened to them before. You’ve probably taken way longer than you thought on a project before, so that means you did it as well.

By getting something up quickly for them to see, you build trust. Then you can keep plugging away on the work at a slower pace, so long as you have progress to show regularly and you meet the dates that you’ve agreed upon.

How Often Do We Communicate?

Something that developers are especially good at is going into “mole mode”. They get involved in a project and just keep focused on it for weeks and end. They barely come up for air, and are getting lots of work done.

I get it, code is a Maker task and Maker’s need lots of time to do their work without interruption. But your client isn’t a Maker. They can’t look over your shoulder every few days to see what’s up.

They figure you’ve flaked out on them unless you keep them up to date. Keeping them up to date starts with a weekly phone call. Yes, you’re going to pick one day a week and use part of it to talk to your current clients and give them an update. I use Tuesday as my day.

But that’s not all you’re going to do. You’re going to update them as a comment in whichever PM system you use on Friday and Monday. On Friday, you’re going to give them a recap of how the week went and remind them what’s on the list for next week.

On Monday, you’re going to remind them again what’s on the list for the week and when they’ve booked their weekly check in. If you need to see a format for this communication then check out Effective Client Email. I provide the templates I use there.

This communication is on top of anything you do to update the project management system as you complete tasks. The Monday/Friday email and the call are the bare minimum you should be doing to communicate with your clients. It’s the least they expect, and it will be about 10000% more than they got from their last freelancer.

Avoiding Scope Creep In your Beginning Freelance Business

The final thing that kills a project is scope creep. That list of things that sound like they’re awesome and just get added to the list. Yes, some of them are good ideas, but the longer that list gets the less likely it is that you’ll launch the project.

When I setup a project I have four lists in Trello. They’re labelled:

  1. This Week
  2. Tasks
  3. Future
  4. Questions/Other

‘This Week’ is updated every Friday and has all the tasks that are going to be done in the next week long cycle. That means on Friday you need to look at your ‘Tasks’ list and decide what can reasonably get done in a week. Only those items go on the list.

This is not a list of the hopes and dreams you have for a week. It’s a list of wha you know you can get done. I’d rather see a smaller list that gets done than a big list that you finish 50% of. When your client see that 50% done list, they’re going to loose faith in you and the project.

The second list is all of the tasks that are in the project. I usually have them organized in the order I think they’ll need to be done in. On Friday, I survey the list and move ever any items that I plan on doing the next week.

Those two lists comprise the whole project that was estimated on. The other two lists should contain nothing that was originally agreed upon.

Next, the “Questions/Other” list. This is where your client puts any questions they have on the project or any other stuff that they enter. In general, clients shouldn’t be updating any of the other lists at all unless they’re responding to something I’ve asked them about or approving and resolving a task.

From the “Questions/Other” list I may move something into the “Tasks” if it is something that is included in the project, but needs to be spelled out better for the client. Most of the stuff that comes up here though ends up in the “Future” list.

The “Future” list is for everything that’s a great idea, but isn’t part of the current project. It’s where all the crazy ideas and nice-to-have things end up. They stay there until you’ve shipped the original project and then produced and estimated and been paid for the new items you’re going to work on.

Even if there is something that sounds like an amazing idea, it doesn’t go in to the current project if it can be helped at all. The more items you move from “Future” into the current project the less likely it is that your project will ever see the light of day.

Your job is to ship a successful project for your client which means you need to help reign them in so that the project is indeed successful. It’s your fault if they run wild with extra items and the project never launches.

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photo credit: clement127 cc

What Good Project Management Tools Look Like

Now that we know what the highlights of running a good project are, we need to look at what you should be looking for in a project management tool. As much as I love and use analogue productivity, I don’t use an analogue system when it comes to managing my projects.

The biggest weakness of analogue systems is that they offer no way to collaborate with your clients. You need to share screenshots, videos, links, and comments all around the tasks that need to get done for the project. We know email is a terrible way to do this, and that an analogue system like a notebook doesn’t allow for any sharing.

So we turn to software.

Easy to Use

The first stopping point is that you and your clients need to find the system easy to use. For some, that may mean that basic Github tickets can work, for others Github is going to be way to complex.

Since you’re going to be in the PM system regularly, it’s important to find one with a nice spread of keyboard shortcuts. Sticking with the keyboard navigation will save you little bits of time all over. That adds up over the year and turns into a large time savings.

Make sure that there are some training videos for your system as well. You’ll need to provide links to them for your clients to use so that they can wrap their head around the system. If your client finds it hard to use the PM system, they won’t use it and you’ll be getting a whole bunch of emails you don’t want to see.

Has Some Templates

Another key in a good project management system is it’s ability to provide you with project templates. You’re likely going to do similar projects and a bunch of the tasks are going to be the same.

You want a system that doesn’t force you to type every little piece in every time. If you have to type in every task for every project, you’re going to forget stuff. Even if you have your own list in a separate application, you’ll forget to move something at some point and then since it’s not written down, it might as well never have happened.

Link to Tickets

One of the crucial parts of your personal productivity (which we’ll cover in a bit) is pulling the tasks out of the tickets and into your own system. You do this so that client updates don’t derail you.

Remember, we pulled out of email into a PM system to make sure that we didn’t get distracted a whole bunch by the emails that come in and don’t relate to the project. The notification inbox of your PM system can turn into the same thing, especially if you have multiple projects running.

You may have your time set aside for Project A, but Project B keeps pinging you and that draws you into answering things for Project B while Project A languishes.

This is why I think that links to tickets is crucial. Then you can take the link and put it in OmniFocus or 2Do or … whatever and work on the single ticket out of your personal system. Then, when you’re done you can click the ticket link and update the single item. Now, close the browser and get to the next task.

Organizing this way will let you get work done as you had planned. It will allow you to focus on the tasks at hand instead of getting derailed constantly.

Wait, I just referenced OmniFocus which is a digital tool and I said I don’t use them. I realize that I’m an outlier here and you’re most likely using Todoist or 2Do or…something. I’ll talk about the specifics of what I do shortly.

Doesn’t Always Interrupt You

One of the best features that BaseCamp introduced was the idea that you can ‘snooze’ your notifications. They allow you to set hours where you won’t get any notifications of any kind. Your boss can’t even change that setting for the company. This means that you can set the no distraction hours up for the whole day even, and never get interrupted.

Which ever system you use, you need to make sure that it can be silenced. Some of that will come from how you work with it. If you use the system I described above, then it’s going to be hard for anything to distract you because you’ve pulled the tasks out for the day and are focusing on them instead of whatever happens to come up.

That also assumes that you silence your phone and tablet and Amazon Echo notifications. All the space you’re building is a waste if you allow other notifications to jump into your life.

How to Integrate Your Project Management System and Personal Productivity

I’ve already provided you a workflow for updating your tasks if you’re using a digital task management system like 2Do or Todoist, but I don’t use either. My personal system is a notebook and mostly follows Bullet Journal.

So, how do I use that system to stay focused on the tasks at hand and then update Trello, which is my PM system of choice.

It Starts with Planning

For about a year before I went with an analogue system I did use the methods above with OmniFocus. I would pull out the ticket link and put in the detail required in OmniFocus so that I could work on a task.

The problem was, I didn’t always get the right information. Somewhere in the back of my head I relied on the link to the ticket for the information I needed. I kept finding that I hadn’t thought through what the task would take before I committed to doing it. That left me with bigger tasks than expected and a day that felt like it was always off the rails.

I still take a task out of Trello and put it in my notebook, but I have to write down a quick sketch of the task, and any conversation that happened around it so that I’m sure I know where it’s at. If there are screenshots that may go with it, I pull them out of Trello and drop them in a folder in my Downloads folder. I label that folder the same as the task I’m working on so that I know they go together. That title matches the Trello card.

Then, I get down to work and when I’m done and need to update the task I open the Trello macOS application and search for the card to update it.

This does take a bit of discipline because I have to ignore the little red bell that Trello shows me when there are updates, but I don’t find that to be a problem. The advantages that have come from pulling out the task, and making sure I understand it the night before I’m going to work on it far outweigh the small friction that results from not being able to click a link directly to the ticket.

For the most up to date reading on Managing Projects for a Freelance Business, see my reading list.

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Personal Productivity in Your Freelance Business

Another component to having an awesome freelance business is getting down to the nitty gritty of getting work done. You can have the best PM system, the best CRM workflow and the best marketing, but if you’re not shipping projects to clients your business will suck.

You won’t be getting any referrals because you’re late all the time.

This is where personal productivity comes in. You need to have a good system, and the discipline to use it so that you can get work done for clients on time and on budget.

The first question that most people ask is some variation of “Should I use Getting Thinks Done or…”. They’re worried about the specific system and tools that they should be using.

Tools almost don’t matter, what matters is you and the process. Does the process fit how you work? Are you going to do it? Most of the systems around provide you with everything you need, if you do the work.

Let’s start by looking at some key concepts in personal productivity so that you can start this journey from the right frame of mind.

I’ll be writing much more about personal productivity coming in February, like 50k words more.

Key Concepts in Personal Productivity for Freelancers

Before you can dive into your personal productivity system there are a few things you need to get straight first. I’ll be covering these key items in short here, as I’ll be covering them in great depth in February.

If you don’t have a handle on these things, then it doesn’t matter what system you use. It will always suck and you’ll never get good work done.

First, you need to embrace constraints. I’ve already talked about how using a paper based system has forced me to better understand the tasks I need to do. The constraint of paper has also stopped me from making a bunch of commitments for ‘future Curtis’ that I can’t meet right now.

Second, you need to be solving a problem if you’re going to change. Most times the issue with a productivity system is you. You change from Todoist to 2Do and feel relief because you have made a bunch of commitments in the form of lists in Todoist. When you change you feel free to abandon those commitments which you never should have made in the first place. The problem is you and the next task manager you use will feel the same way in a bit.

Third, nothing is going to solve every problem. There are things that I don’t love about my paper solution but it has so many benefits that I just deal with the things that it doesn’t do well. The freedom it gives me far outweighs any drawbacks. Give up on finding the perfect system.

Fourth, you have to be willing to make decisions. All those crappy lists you hate, just delete them. Stop pushing it off on the future. Admit you’re not going to do it and leave it there.

Fifth, you need to work based on priority. Ask yourself every day “What is the single thing I can do today that will make the rest of my job easier or irrelevant?”. Then do that thing and be okay with sucking at other things.

Sixth, plan to the now. Just because you started an internal project 6-months ago doesn’t mean it’s the thing to do now. Don’t fall for the sunk cost fallacy. When you look at your goals every quarter, just do the ones that provide the most value now.

Seventh, write it down or it didn’t happen. If you’re not tracking your tasks then it didn’t happen. You won’t remember it and that can be a good thing because so often we write down crap that sits on our back and stops us from getting something awesome done.

Eight, manage based on energy. Not all of your day is equal. Sometimes you have the energy for hard tasks and sometimes you don’t. Make sure you schedule your ‘hard’ work in to the times that you have lots of energy. Brent Hammond and I had a great discussion about tasks and energy. I’ve also written more about managing your tasks based on energy in a bigger series on deep work.

Ninth, make sure that your environment is set up for focus. If you have a bunch of crap distracting you all the time then you won’t be doing awesome work. Set your phone and tablet up for the tasks they’re meant for. Set your laptop up for no distractions. Make sure your work environment is clean and clear.

Now, if you’ve got a handle on these things, you’re ready to start digging into personal productivity. If you don’t have those things dealt with, then no system is going to work for you.

You have too much crap in the way of getting good creative work done.

Which Personal Productivity System is Right for You?

While you may be looking for a specific tool recommendation, you won’t find that here. In February, I’ll walk you through what I do, but even that may not work for you. Most of the time, looking for a new tool is a waste of your time.

For most people, the problem with your current system isn’t the tools it’s you. You don’t do your weekly planning or your daily planning or review all your projects. You maybe make a task list for the day, but maybe not. You might default to email and what it thinks is important for you.

Then you wonder why you feel overwhelmed all the time, but you shouldn’t. You do it to yourself and the next tool you choose will have the same issues.

As you think about your personal productivity here are a few more rules to think about.

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photo credit: curtismchale cc

As Few Pieces as Possible

A great system has as few pieces as possible to be productive. My system has a pocket notebook for on the go notes. A Bullet Journal from Leuchtturm1917 for my planning and task management day to day and finally Trello for my project collaboration.

There is nothing else that deals with any of the tasks I have day today.

I don’t have a CRM tool that’s stand alone anymore because it was an inbox I never checked and thus wasn’t getting any value out of. I moved my CRM into my notebook along side all the other tasks that I need to get done in a day.

One item I didn’t mention here is my other notebook, the one that only handles my notes on books. This is outside of my Bullet Journal because it’s got it’s own function. The only thing that goes there are notes on books and ideas for writing that are sparked by the reading I’m doing.

I like analogue systems because it entirely breaks me out of the possibility of anyone dictating what’s important in my day. Yes it makes more work because I have to take detailed notes on what needs to get done so that I don’t have to dive back into Trello or email, but planning is key to having a day that accomplishes something worthwhile.

Adapt it

Your system must also suit how you work. You can’t import my system and figure it’s going to rock your world. Maybe it will but not in a good way. Look at the ideas that come from other people and use what works for you. Throw out the rest.

I don’t use the Bullet Journal system by the letter. I don’t use GTD either, or Kanban or stuff from the 12 Week Year. I use a mash up of all those systems that works for me.

As you journey through building out your own personal productivity system, make sure you refer to the key principles in the last section. Make sure that you write down the problems you have and as you go looking at what others are doing, you import what looks like it might fix your problems and toss the rest.

Keep piloting change in your system. Your personal productivity system is not stagnant. Your work will change. You will change. Your system should change with you.

Review and Planning is Key

Out of all the systems out there, I think that the one common required piece is a review process. A good weekly review of everything you have on your plate is crucial to success. A plan for the week ahead and a daily review and replan in a key element in getting things done.

You can’t wing it and hope to have a bunch of great output. Winging it will mean that you continue to be stuck in the weeds trying to find your way out as you drown in your work.

You Must Create Space In Your Day to be Productive

If you want to get things done, you need space in your day. With a day that’s planned down to the minute with must do tasks, you’re never going to feel like you’re getting enough done.

One of those tasks will go longer and then all the other commitments you just made to yourself will stack up until you’re working late again and still not getting everything done.

The maximum percentage of your day that should have must do items is 60%. Anymore than that and you’re planning yourself into problems.

One of the key reasons that this happens to people is because they allow distractions to creep into their day. All your planning should surround the need to get focused amazing work done. With four hours of focus, you can get more done than most people can in eight hours.

You have to cut all the distractions to get that focus though and to do that you need to be familiar with the two modes of work.

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photo credit: clement127 cc

You’re a Maker and a Manager

You’re both a Maker and a Manager. Makers need large blocks of time to do focused work. That’s writing, design, thinking, coding, or anything creative.

If you’re running a business, you’re a Maker and you need to make sure you have time aside to focus on the tasks that are important.

But, you’re also a Manager. You probably have to have sales calls and meetings with clients. You need to answer and respond to email and maybe even jump on social media to update some profiles and such.

The problem comes because most people go Manager first and Maker second. This is a problem because Manager tasks easily overflow into Maker tasks. Email always takes longer than you think, and it always brings up random crap that others think is important.

Instead, go for Mullet Productivity, Maker in the morning and Manager in the afternoon. When you plan your day, make sure you have the details needed so you don’t have to dip into the manager spaces in your work. Give yourself at least three hours of focused time to do your Maker work.

Then be open to Manager work in the afternoons when your brain is tired and has less energy to dive deep into big thinking tasks. I do this and I plan in a 2 – 3 hour break in between my two modes of work so that I can recharge my brain and have the energy required to dive into more work later.

You can’t be on for eight hours thinking hard about your work. You progressively make worse decisions and you can’t afford that. Give yourself a planned break in the day and when you’re working only work. Ignore distractions and focus on the most important tasks at hand.

Plan Space

Outside of planning your tasks out for the day, there are other items that need to get in your week. First, you need unplanned time every day to deal with the extra stuff that gets tossed your way. Second, you need rest so that you can focus. Finally, you need at least three hours a week dedicated to self-improvement.

No day is ideal. In fact while you may have an idea day plan, it will almost never happen. Kids will get sick. A client will have a legitimate emergency that you need to deal with. Your computer will crash and you’ll have to figure out why. If you pack your day hour by hour with tasks, you have no flex to deal with these things. Make sure you have a working hour every day that has nothing officially planned for it. Leave it for overflow so you can deal with what life throws at you.

Second, you need rest every day so that you can focus. Your schedule may not suit three hour chunks of rest between working blocks like mine does, but it certainly can support a 20 minute walk. If it doesn’t, your business is broken. Admit it and start the hard work to restructure it so you can have that walk every day.

Finally, a solid business means you have three hours every week to improve yourself. If you’re a developer, that’s not just looking at new code, that’s learning to run an amazing business. Same goes for designers or writers. You must be reading and learning about marketing your business, planning better, how to write better proposals. If you don’t have time every week to do that, then you’re on a long slow death spiral. You won’t be getting ahead like dream without the hard work required to be better in the fields that aren’t directly your work.

If you can build in this space, and stick to the processes required to have awesome personal productivity, you can get the work done you need to without needing 12 hours a day.

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Are You Going to Build a Viable Freelance Business?

Now ask yourself, who are you?

Are you someone that just wants to focus on the craft of code?

Do you want to write, and hate marketing?

Who are you going to partner with to do the stuff you don’t like? Who is perfectly suited to filling in your gaps?

Back at the beginning of this, I said that you needed to figure out who you are. Are you willing to do the work needed to build a business? Are you going to admit you’re in sales and must address marketing in your week?

Are you only interested in writing code day in day out and want to deal with clients as little as possible?

One other option we didn’t go into if you just want to do your craft, is that you can find a partner. Someone that loves the sales and that you trust to take care of the things you don’t like.

If you’re not sure who you can tap on the shoulder, then start looking for them. Look with intention. Find someone that loves the parts you hate.

If even that step sounds like work you don’t want to do, get ready to fail. If you hate the marketing and selling of your business, then no one will be doing it for you.

If you struggle with client relationships and getting projects done on time, then you’ll have a dry well of referrals. Why would anyone refer work to you if you’re over budget and late all the time?

If you want to run a successful business, you’re in sales. You must get into the marketing tasks. You must plan time every week to get better at the tasks that aren’t directly a part of the work you sell.

You must have a plan each week to be focused on doing awesome work and you must stick to it. You must say no to the distractions that are around so that you can get awesome work done.

If you’re not going to do these things, go find a job and stick to what you love. There is no shame in that. It’s the right choice for some people. It might be the right choice for you, if you’re not willing to do the hard work it takes to run that business you dream of.

Have an awesome day!


PS: If you’re looking to start filling in some of your holes, you should join my 8 Week Business BootCamp. It will help you set goals and build the processes you need to have a kick ass freelance business.

first photo credit: elstruthio cc