Almost Fearless

Becoming a Digital Nomad – Small Business Edition: Day 23 of 30w30d

This post is part of 30 Ways in 30 days to Redesign Your Life and Travel the World. This series seeks to give you the practical, real world steps you need to take to get from wherever you are, to exactly where you want to be– traveling the world and living the lifestyle you want.


30 ways in 30 days, digital nomad, small business, travel world,

I started a small business in 2002 with my husband.  It was a little design studio, we had a sales staff and some artists working for us, and an office space across the street from Starbucks headquarters in Seattle.  We walked into the business will very little cash (we had both been laid off from our dot com jobs) but with plenty of energy and enthusiasm.  The business did fine.  We made about what we would have made working full time at that point in our careers.  We were able to pay for the S-Corp status and a lawyer.  Our rent and business phone/internet checks never bounced and we paid our staff on time.  However, after a year we closed it down and got regular jobs.

Why?  Because it sucked.  We were essentially working as full time freelancers plus running a business, overseeing staff and trying to find and woo clients.  It was a 7 day a week, 17 hour/day job.  Talk about burnout.

I’m convinced it’s not the way it has to be.  We tried to use the same skills we used in the workplace for our business.  The problem is that when you’re an employee, working hard is rewarded.  When it’s your business, it’s about working smart.

Our biggest mistakes:

1.  We didn’t have cash. This forced us to take on clients that paid little and go after a quantity strategy approach verses quality.  We were scrambling from the beginning.  You don’t want your cash flow to determine your business strategy, that’s a very bad approach.  It’s short-term thinking and what happens is that you are too busy to chase quality work as much as you should or create any systems that would lessen everyone’s work flow.  You might identify inefficiencies but be powerless to do anything about it.  The business is running you.

2.  We got an office space too soon. We worked for about a month in our basement, and we should have stayed there for the whole first year.  It felt like we needed a real office to be legit, but the truth was that we could have saved all that money and reinvested it into the business in ways that would have increased our bottom line.

3.  We didn’t outsource enough. We tried to do everything — I mean everything ourselves.  I was building databases for clients, designing our website, taking on every project.  Thinking we were milking all the value out of the project by doing it ourselves, we were actually missing an opportunity.  We could have actually earned more by outsourcing.  We would be able to take on more clients, focus just on our core competencies and waste less time.

4.  We didn’t focus. If the work was there and it was even tangentially related to design, we took it.  At one point we were doing voice over work for a medical video on varicose veins.  Not exactly what we had planned in the beginning.  Because we didn’t focus, we never became specialists in any one area.  We missed out because we tried to be everything to everyone.

5.  We didn’t create systems. The number one piece of advice I’d give anyone trying to start a small business is to plan yourself out of it.  Every single thing your company does, must be done by someone else.  You’re running the business, not literally running it.  You are not every employee.  Your job is to think about how to make more money.  If you’re answering phones, pitching clients, doing the work, updating the books and sweeping the floors at night, you don’t have a small business.  You have a freelancer.  You.  The first thing to think about is getting everything off your plate and how to monitor that with the least amount of daily involvement.

We didn’t fail completely.  We did manage to pull in a healthy income.  We did gain some name-brand clients.  In fact, one client was so impressed with an animation we did, he offered my husband a full time job, working remotely (the job my husband still works to this day).

What We Did Right:

1.  We worked sales, hard. We didn’t sleep, but we did pitch everyone we could: Yahoo, Ebay, Major League Baseball, you name it.  Sometimes we’d get the work, other times not.  In the beginning we spent most of our time creating mock-ups, free samples of our work to show off what we could do for each potential client.  If you’re just starting out, it’s the only way to land someone big.

2.  We didn’t waste our time with free work seekers. In the design world,  there are lots of people looking for free services.  They tell you, “you can put this in your portfolio!” which is just silly.  A more subtle trick is when someone puts an ad asking for a logo design but wants to see mock-ups first.  Rule: get paid first, then work (unless you approached them first and they are a big name, see above #1).

3.  We reached out for help. I went to the Small Business Administration and got connected with some mentors who actually ended up throwing me thousands of dollars worth of work, plus the invaluable advice they gave me.

4.  We took care of the accounting and legal structures. It was a pain, cost money, but it was one of the smartest things we did.  If we had ignored it, we could have been hit with massive taxes, since our company did over the six figure mark in the first year.  It didn’t feel like a lot, because after expenses and our salaries we were just squeaking by, but at tax time it was a life saver.

5.  We cared about doing extremely good work. We treated every project as a potential reference so we really gave 110%.  This made such a big difference in our retention rate.  We knew if we could just convince someone to take a chance on us, that we could make them very happy.  Every time we kept a customer, we had more time to look for other work.  Ultimately, this lead to my husband’s current job, which as 100% remote is part of what lets us travel full time.

Last Word

If you can, I’d suggest saving enough money so that you can afford to hire people to do the work for you.  It’s a full time job to analyze the market vs. your strategy and your time is best spent doing that.  You need to figure out how to do things cheaper, better, faster.  Let someone else do the repetitive tasks.  Good luck!

pic: lavarue

Christine Gilbert

I’ve been dragging my husband around the world since 2008 always with the promise that, “Yes, Drew there will definitely be hammocks there.”



  • #5 – extremely good work.

    Ayup. I’m a freelancer too and I have turned down work when I’m not sure I can deliver the best possible work. It KILLS me to do so, but I would rather walk away from projects than deliver less than my best work. It means I don’t book myself as tightly as I could, but really, is it worth it to screw up the project? Or is it better to tell the client you just can’t get their project in right now but would LOVE to do some work for them when you have more time in your schedule? I vote for the path that means repeat work.

    Good stuff and good reminders even for someone who’s been at it a while. Thanks.

  • Excellent post Christine. A lot of people don’t fully understand what it takes to run a small business and/or personal brand. Some want to make money quickly in such a big bang fashion all the while losing quality and what made their brand unique in the first place.
    .-= Lola´s last blog ..For the Love of Short Sentences =-.

  • Thanks for sharing your experience with us. I’ve considered for some time going independent and starting my own business but I’ve held back a bit because of costs, time, and energy.
    .-= Carolina´s last blog ..Get Healthy and Fit, Part 1 – Habit Edition =-.

  • Dear Christine…wow, this is like reading a chapter out of my life. My university degree is in graphic design. I went through most of what you write about in this post.

    The worst part is people thinking creative work should be spec up front, cheap, or just plain free.

    BTW, I also am adding you to my blogroll.
    .-= The-Digital-Nomad´s last blog ..Where can I find freelance writing jobs online? =-.

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