12 things I learned after one year running a freelance business

10 min readMar 19, 2015

A year ago this month, I launched Flying Dog Creative. It’s been exciting, stressful, challenging, liberating, and a lot of fun.

Back in May, I wrote about ten things I learned in the first six months. In that post, I talked mostly about how and when to make the jump to freelance, and about getting things started.

Looking back on the first year, here are 12 things I’ve learned about keeping a freelance business going and thriving. After six months, I’d learned how to swim. After a year, I have a better perspective on moving forward and picking up speed.

1. You’re not “a freelancer” or “freelancing.” You’re running a business.

This may seem like semantic difference. It’s not. When you say “freelancer,” many imagine some semi-unemployable solo worker who loiters in Starbucks or sits at home drinking Hershey’s syrup straight from the bottle.

Designers and writers don’t tend to think of themselves as entrepreneurs, but that’s exactly what you need to be to maintain a full-time freelance career.

Designers and writers don’t tend to think of themselves as entrepreneurs, but that’s exactly what you need to be to maintain a full-time freelance career. You need to embrace your identity as the force behind a bold, growing business venture. Even if your company has one employee, it is a business. You’re bigger than yourself.

When people ask me where I work, I never say I’m a “freelancer”: I tell them I run my own design company, which is 100% true. That’s how the IRS and my state views me. I’m not “self-employed”; I run a business. And that’s how I present myself to potential clients. I tell them about the work I do and the clients I work with. Like it or not, you’re going to be responsible for all the accounting, marketing, administration, and housekeeping of your business; you might as well accept that and stand tall as a business owner.

2. Be on time. Be responsive. Don’t be a jerk. That alone puts you ahead of most of the competition

Back when I was single and going out on first dates, I was always surprised that women I met were often impressed with little things I thought were ordinary: I showed up on time. We could have good conversation and I’d ask them about themselves. I’d offer to pay for dinner. Apparently, a huge percentage of men (at least in the Metropolitan DC area) failed at one or all three of those simple things.

And now as I meet and work with new clients all the time, I hear a lot of horror stories about their past experiences working with designers or developers. It’s deja vu: a lot of the same complaints I heard from the dating world. People they hired in the past usually committed one (or all three) of these sins: they missed deadlines; they didn’t communicate or listen well; they didn’t deliver what they promised. There’s an old saying in the design world: “Good. Fast. Cheap. Pick any two.” And yes, it can be challenging to deliver all three. But too many freelancers only deliver one of those three. Or none.

I get a surprising amount of credit for doing the stuff I thought you were supposed to do: be nice and do good work on time. It’s a good reminder that while your technical and creative skills matter, a lot of the time, your “soft skills” are equally or more important: get the little things right and you will stand out from the crowd.

3. Working solo helps push you to grow, improve, and work smarter.

A dirty secret of working as part of a design team, whether in-house or at an agency, is that you can get a little bit comfortable doing a few things again and again.

When you no longer work for a team, or manage of team who can handle parts of a project, it forces you to stretch and get better at every aspect of a project. If you can no longer lean on colleagues to handle web development, or logo design, or wireframes, it’s up to you to take on all of the above.

Freelance work forces you to cover a wider range of requests. Aside from designing and building websites, I’ve been asked to handle advertising, print projects, email design, branding and logo development, and content strategy. It can be challenging, but it keeps you sharp and more in tune with trends in design and technology. It pushes you to figure out better ways to get things done more quickly. When you are your own boss, you have more motivation than ever to be efficient and make the best use of your time.

4. Just Pick Up the Phone.

Communicating well with clients is essential, especially early on when you’re establishing trust and a good working relationship. Newer technologies would seem to make this part of the job easier, but from my experience, a traditional phone call is almost always better than email or video.

Email is still the most common method of business communication today, but quite often a back-and-forth exchange can take hours and result in miscommunication. A three-minute phone call can often clarify and eliminate the need for a cumbersome email exchange. Text communication easily lends itself towards misunderstandings. And instant-messaging is even worse. People apply their own interpretations and momentary emotional states to words on the screen.

Video calls via Skype, FaceTime, or Google Hangouts give you a live face-to-face experience, but often get bogged down in technical glitches, even between tech-savvy people. Unless you’re doing a screen share or something that demands synchronized video, a voice call is almost always better and more efficient. Instead of spending ten minutes sorting out audio or video miscues, you can get right to it in the first minute.

Bottom line: the best and most reliable way to connect with your clients is still over the phone. You will usually save time and avoid miscommunication. Stop being an introverted dork and dial your client.

5. You Never F’ing Know (A Cold Call Might Work).

Earlier this year, I stumbled onto an insightful, well-written article with valuable parenting advice, but I couldn’t get past how horrible it looked. The website was ancient, clunky, and painful to read. If ever there was a website in need of a redesign, this was it.

On a whim, I emailed the psychologist who wrote the article and told her how helpful my wife and I found the story to be and thanked her for it. I added that I felt that her website didn’t do justice to the quality of her work and that if she ever wanted to redesign it, I’d love to work with her.

To my surprise, she wrote back a day later and wanted to hear more. A couple emails and phone calls later, I had a new client.

I don’t make it a habit of finding clients in this manner — work usually comes via referrals — but this experience taught me that work can come from surprising places. A shot in the dark sometimes hits its mark.

6. Some prospects will pass; that’s OK.

On the other hand, sometimes you find a promising prospect, have good initial conversations, put together and send them a solid proposal, and then… nothing.

It doesn’t mean you did anything wrong; sometimes it just doesn’t work out. That’s the nature of the business. Babe Ruth didn’t bat 1.000. Michael Jordan missed 12,345 shots. A big part of running a freelance business is finding work, and sometimes that means you’re going to go after something that doesn’t pan out. Shake it off and move on.

7. Oreos are evil. So are their friends.

I gained about eight pounds earlier this year, which I attribute mostly to the proximity of my home office to the kitchen (about four feet). Oreos (and their healthier but equally evil Whole Foods alternatives) were the biggest culprits. Other horrible things to keep nowhere within walking distance of a home office:

Leftover birthday cake
Cookie Dough ice cream
Pirate’s Booty
Crescent roll dough
Your children’s Halloween stashes

8. Homegrown templates can simplify and speed up the boring stuff.

Putting together proposals and contracts are like eating your vegetables. You know they’re really good for you, but you still would rather dig into just about anything else.

For a while, I tried services like QuoteRobot or Bidsketch, hoping they would make the process easier and faster, but found it to expensive and limited. I realized that it was easier and simpler to just create my own templates for proposals and contracts.

A great model for legalese-free contracts is Andy Clarke’s Contract Killer. I started with that as a base for my standard contact, customized it, added my company branding, and then created a few different versions: one for websites, one for logo/branding work, and one for projects with a mix of print and digital work. Now, whenever I need to prepare a contract, I start with one of these, updating a few details here and there, and it can be sent out to a prospects quickly.

I have similar templates for proposals: a basic, branded Word document that provides potential clients with a project overview, a breakdown of the work, a time estimate, a proposed budget, and information on how to move forward. It looks polished and professional, with all the flexibility I could need to tailor it to quickly a particular project.

9. Working for free is (almost almost always) a bad idea.

When I started the company last year, I’d already heard Jessica Hische and Mike Monteiro‘s warnings against working for free. And yet, I made that mistake once this year, and the result was a mess, one of the few projects this year that really ran into problems.

Unpaid work is bad for a number of reasons. There’s the fundamental principle that designer’s experience, skill, and talent is valuable and shouldn’t be given away for free. Creative professionals don’t need to act like we work for spare change. Every free design project undermines the professionalism of the design community. Secondly, it can be hard to put a “free” job ahead of your paying client work. As a result, it will linger in your to-do box longer than you thought.

But most importantly, when someone isn’t paying for your work, they are less likely to value it. When a client doesn’t have to think about an incoming invoice or a project going out of scope, the time and effort put into the work has less meaning. As a former in-house designer, this is a familiar pattern: internal design teams often struggle with the misperception that their time and services are “free,” and therefore can be taken for granted. As a result, it’s easy to wind up with scope creep, indecisiveness, and a project that becomes bigger, messier, and more challenging than you expected.

Doing a project for free may seem like a nice thing to do, or maybe even a way to open the door to future work via networking, but most often, that “freebie” may take a lot more time and effort to complete than you expect. And worse, it can drain productive time you need to spend on paying clients.

10. If you do it right, you’re never really working alone

11. You are your own project manager; get a good tool for the job.

When I started the company last year, I essentially had four active clients. By last summer, my client list had grown from to 14. At one point, I had 12 projects in the works at the same time, and keeping track of everything became daunting. I felt overwhelmed.

I’d outgrown a simple to-do list or calendar. I needed to be able to plan ahead, avoid colliding deadlines, and see how many hours I had committed on in the days and weeks ahead.

I experimented with the most popular project planning tools and services, but most of them are geared for teams, not individuals. Next, I tried a few Gantt chart tools to help me visualize overlapping deadlines and time commitments, but while they helped review the big picture, it didn’t help with smaller day-to-day planning challenges. It was hard to zoom in on a single day and plan it out.

Finally, thanks to a chat with the Home Work podcast’s Aaron Mahnke, I discovered OmniFocus, which delivers a great balance of short- and long-term planning, synchronization between all my devices. It has allowed me to organize everything by client and project, keep it all scheduled and planned out, with a wide range of ways to view and sort all that information. Omnifocus isn’t cheap ($40/$80 OSX; $30 iOS/iPad, $20 iOS/iPhone), but it’s allowed me to get in control of multiple project, deadlines, and deliverables. Just for the reduction in my stress level, it’s been well worth the money.

Recently, I’ve also started tinkering with Todoist, which seems promising as well, for many of the same reasons. And unlike Omnifocus, it’s available for Windows/Android users.

12. Going freelance is the best career move I ever made.

There are certainly downsides to running a freelance business: uncertainty, erratic workloads, occasional late payments from clients, and the risk of social isolation. I also miss out on NFL pick’em pools and leftover bagels from early meetings.

The freelance life isn’t easy, but I wouldn’t want any other one.

So it’s not perfect; it’s still a job.

But it is the best job I’ve ever had, and it’s not even close.

I’ve met and worked with a wide range of amazing clients: everything from small entrepreneurs and family businesses, to savvy nonprofits and innovative consulting teams, to community credit unions, to undefeated sports teams, and to nonprofit groups trying to make a better world.

I’ve enjoyed tremendous freedom and flexibility that I never had in any previous workplace, and still been able to make a great living.

I’ve become a better designer, a smarter entrepreneur, and a better time manager.

I’ve worked hard but still had time to drop off my kids at school in the morning, walk my dog at lunchtime, and sit at the dinner table with my family almost every night.