Eight things I learned after two years freelancing full time

Two years ago, I resigned from my job and launched a full-time freelance design and web strategy business — 750 days ago to be exact.

I’ve written about what I learned after six months and after one year. With another year behind me, here are some more thoughts on the ups, downs, challenges, and solutions to running my own business.

1. Life can get in the way of business

A year ago, my father’s health took a sudden turn for the worse. Cancer, which had been in remission since 2013, returned. His health rapidly deteriorated. I spent time traveling back and forth to Chicago and Los Angeles, trying to help my parents, and in the end, heading home to be with him in his final days. In March, Dad died.

The end of 2014 and the first quarter of this year were challenging. The emotional and mental stress were personally difficult, but they also took their toll on me professionally.

In the big picture, of course, family is much more important than work. But as a business owner and freelancer, there is no sick leave or family leave to take. With limited time to focus on client projects and billable hours, I had no one to whom I could hand off client work. Nobody else could market the business and find new clients while I was consumed with my family matters. As a result, business slowed a lot for three months.

I was blessed with some tremendously understanding clients. I also managed to work in short, focused stretches to stay on top of a few projects during this period — enough to keep things moving. And we fortunately had enough in reserve that the downtime wasn’t crippling. It was a harsh lesson that, when you work for yourself, there is little support when things are tough. I spent many months playing catch-up.

In retrospect, I wish I had better prepared for the unexpected by lining up support. Had I better established a network of designers and developers I could team up with, I might have been able to keep the engine moving during the worst of it. I learned that you’re on own as an entrepreneur, but you should prepare for real world emergencies by lining up some backup help, just in case.

2. You may outgrow your home office

I ran this business out of a third bedroom in our old apartment for about 18 months. For nearly two years prior to that, I worked remotely for a job out of the same home office. It worked well for me, but eventually, I started to itch for some separation between work and home life. When you live and work within the same space, it’s hard not to have those lines blur. The home office gave me flexibility and freedom, but it could often feel isolating and claustrophobic. Days would go by when I rarely stepped outside.

So this year, although it would add to the cost of the business, I opted to find a small office space away from home: a quiet, separate, and distraction-free space to work and run the business. It’s made a huge difference.

I still work from home from time to time, but I’ve learned that an outside office — even a desk in a shared workspace or coworking center — can give you extra breathing room to focus and improve your outlook.

3. It’s worth it to stand up and speak

I spoke at two conferences this year, talking about design and web strategy. You can watch my WordCamp Asheville talk on “A Design Survival Kit for Non-Designers” here.

Both experiences were immensely rewarding, but also a ton of research and preparation. The presentations were fun and allowed me to meet a lot of people doing fascinating work in the nonprofit and technology worlds. And the process of getting ready shifted me back into learning mode: going back to basics, rereading books and articles, and thinking a lot about how to explain complex design ideas. It raised my appreciation and admiration for great conference speakers, who make their ideas so interesting and entertaining. It’s a big challenge to cover a lot of material, yet make it feel conversational and natural. The best speakers make it look easy. It’s not. In the meantime, I’m looking forward to speaking professionally at more events in 2016.

4. Get back to prospects quickly, or you may miss an opportunity

Last spring, a prospective client contacted me, hoping I could help them with a medium-sized project. They said they’d heard great things about work I did with some colleagues. We talked on a Monday and seemed to have a good conversation. It was a great organization and a project I would enjoy. I told them I’d get back to them with a project proposal, after which we could talk further and, hopefully, get things started.

But that week got hectic. A few other client items took my focus. Then one of my kids got sick and had to come home from school. Before I knew it, it was already Thursday and I hadn’t gotten back to them with the project proposal. That afternoon, I finally started writing it. I was nearly finished, when I emailed my contact there with a quick question. She wrote back to say that they appreciated my interest, but had decided to go with someone else for the project.


I’ll never know if the person or agency they chose was their first-choice all along. Maybe I was always the second or third bid they needed. But maybe I’d have had a great chance at landing the project had I responded within a day with my estimate.

Either way, I screwed up. I had a foot in the door and didn’t do what I needed to try to close the deal. Worse, I didn’t even do enough to give myself a chance. They seemed interested, but I made them wait nearly four days to get them what they needed to make a decision about hiring me.

Lesson learned. Since then, my rule is to always get back to a prospect within one business day when I’ve promised a proposal or estimate. You never know who you’re competing against. You don’t know how many other firms or designers they’re talking to. Just because the prospective client doesn’t tell you that you’re competing for the job, most likely, you are. Assume you’re fighting for that client and act accordingly.

5. Do your books right or pay the price later

I’m good at a lot of things, but bookkeeping isn’t one of them. At the end of last year, I realized my QuickBooks account needed help.

When my wife and I wanted to start looking at houses in the area, we discovered the bank wanted to see not only up-to-date business books, but also a filed corporate return. We had neither. And getting my accounting in order for either turned out to be a huge task.

Had I been more vigilant and kept my books in order — or better yet, paid an accountant to keep them straight month-to-month — we could have avoided major headaches. Instead, I spent several miserable late nights hitting my head against my desk, trying to sort everything out, making a lot of mistakes, and then ultimately paying an accountant to clean up all my books.

6. Vacations cost money twice; plan and save for them ahead of time

Me, my daughter Angelina, and our dog Ace last summer

I never really appreciated how great vacation pay was until I didn’t have it any more.

When we took a week off last summer to spend time at Hilton Head Island, it was a bit daunting. I wasn’t earning anything that week and the vacation itself was expensive. We had a great time, but when I got back, I was gripped with some anxiety — I needed to play catch-up in a big way.

For solopreneurs and freelancers, this is a familiar challenge: when you work for yourself, there’s no paid vacation time. The best you can do is plan ahead and try to stash away some money from earlier in the year to pay for that time off in the summer. Of course, I didn’t do that and added new stress to my life in an already challenging year.

So lesson learned for 2016: start planning (and saving money in a special account) for summer vacation in January. It’s an old fashioned method that even kids learn, but it’s one to remember. Putting away a little bit each week will allow you to give yourself the “vacation pay” you need to help you fully enjoy swimming, playing mini-golf, and diving over the waves.

7. Slow times happen; stay focused on the work in front of you

I had read and heard other freelancers talk about battling through slow times, but until 2015, I’d been lucky enough not to face it myself. Until this year, I was typically juggling six to ten clients at any given time, and my bigger challenge was staying on top of it all.

But 2015 was a bit different, and when a few major projects wrapped up, I didn’t find immediate replacements. Business was steady, but it wasn’t quite as effortless as it seemed in the past. I felt more stress about the future and about the need to market and promote the business.

It’s one thing to understand and acknowledge that there are ebbs and flows to life as a freelancer or a consultant, but its another thing to ride through it yourself and feel the anxiety of not knowing exactly what you’ll be working on in six months. You may feel confident and believe in yourself, and still feel a little scared.

I wish I had an easy answer or solution for others facing this stress, but I’m not sure it exists. The best thing I can say is to focus on the work in front of you: keep working hard, doing good work, and handling clients with professionalism. As Rocky Balboa tells young Adonis in Creed, “One step. One punch. One round at a time.” Don’t get ahead of yourself. Or, as I advised other freelancers last year, “Be on time. Be responsive. Don’t be a jerk.

So far, for me, that’s the key to keeping new clients and projects coming.

8. The little things make it all worthwhile

Looking back on this list, I hate to give the impression that running a freelance business is fraught with only stress and challenges. And while it is true that this year hasn’t been easy, personally or professionally, there are things the freelance life gave me that are hard to measure.

— When you work for yourself, you have a lot of freedom you never could have imagined when you worked in an office. Want to go take the dog for a hike in the woods at 11 a.m.? Sure. Need to work from Pennsylvania for a week? Why not? Want to go see Avengers: Age of Ultron on opening day? Check. As a freelancer, you will work as hard, probably harder, than you did in a “regular” job, but your day can be a lot more flexible and free than it ever was when you had a timesheet.

— I work with a wide range of great clients. One of the best things about working solo is that you see new faces all the time. I’m inspired by different things my clients are fighting for and trying to build. It’s a blast to work with a team and help them solve problems. In the past year, I’ve worked with large organizations, small businesses, nonprofits, and one-person shops. I get a charge from meeting and working with new clients that I never used to get in my regular, full-time, in-house jobs. Something new and different is always just around the corner, and that keeps things stimulating and exciting. It’s a huge perk of the job.

— I drop my girls off at school every day and pick them up twice a week. I almost never miss a class field trip. My flexible schedule gives me extra time with my kids, and we’ve spent that time well: bouncing in trampoline parks, swimming in pools, exploring museums, and seeing movies. I read to them; sometimes they read to me. I hear about their days, about what they’re thinking about, and what makes them happy. It would be harder to have as much of that kind of time with them at a conventional job.

As a father, I see how fast my kids are growing up. At times, it all seems to be flying by too quickly. And if I’ve learned one thing this year, it’s that life is short and not something to take for granted.

A freelance life, despite its up and downs, gives me the chance to slow down and enjoy it all a little more.

Originally published at flyingdogcreative.com on December 17, 2015.

Delivers communications strategy and content development at Flying Dog Creative. Freelance nonfiction writer. Overmatched father of two girls.

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