What’s just as hard as starting a business?

Spend the afternoon, you can't take it with you. Annie Dillard

Staying in business. 

When you first start freelancing, you have this drive and this rush to prove yourself. Any assignment feels like a magical lick from a hamburger unicorn. (In fact, I remember almost crying in joy to receive an assignment that paid $35 an hour… which is great for a PT job, but DEATH for a freelancer!). But when you get a little into it — a little more skilled, a little more confident, a little more cynical about what’s “worth your time” you have to do something just as hard:

Run an actual business. 

I just started Michael Port’s Book Yourself Solid book, and the first part of the book is already forcing me to answer some hard questions.

I’ve played the field, I’ve seen what I can do and for whom. And now I have to figure out what I WANT to do and who I WANT to do it for. It’s hard to “pick something…” and in fact, it’s almost as hard (and feels as risky) as when I first started freelancing. My first impulse is to serve everyone. But the book outlines some practical, effective points about the dangers of doing that. It includes burnout (which I am totally experiencing), dissatisfaction with my business (which is dangerous, because the whole point of freelancing is to feel more free!), and straight-up not succeeding because no one understands what you can do for them (would you hire a guy who practices medicine on the side?).

But in reality, making the choice — looking at how I “feel” about my business — is really, really hard. For so long, I only had eyes on the $$. I still eye the $$. But I’d love to be excited to pick up my phone every day. I’d love to work with people where I’m mostly just thinking I get paid to do this?!? And when I’m honest with myself, I only feel that way about half my work.

Of course, as fate would have it, more of my income comes from the other half ;-).

So therein lies the risk. But you know what they say: no risk, no glory. I’d like to add to that with a few of these:

No discomfort, no change.

No change, stagnation.

Stagnation, death.

The morbid part of my brain wants to remind you that we’re all going to die (sorry!). So what are we doing with our time, knowing that’s what will happen? Pursuing security (in many different forms)? Getting out of one cage and into another? Avoiding change and pain for fear of what might happen?

Let’s focus on the positives. What COULD happen if we change? What COULD happen to my business if I mostly worked with people I like? What COULD happen to my income if I feel inspired and excited most days? And how can I continue to remind myself of those possibilities when I’m tempted to think about the risk?

Here’s 6 Reasons Why Successful Freelance Businesses Run the Same As Big Companies


There’s something funny about freelancing.

You think you’re escaping all these office things like long work days and micromanaging bosses.

But the real difference? Is that you now have to do those things for yourself!

Here’s a sampling of things you think you’re escaping as an entrepreneur but really you just have to do for yourself now:

  • Established office hours. Sure maybe there are less of them, but freelancers agree that regular hours make you more productive. Which is kind of funny — you leave the 9-5 to escape the 9-5, only to be consumed with business things/ideas from 9-5! In almost 2 years, I haven’t regularly done anything particularly crazy during business hours because I’m trying to hustle. Maybe that will be my summer resolution: a field trip each week during “office hours.”
  • Tracking time. Even if you don’t get paid by the hour, a savvy business owner always tracks how much time they spend on what. It’s the only way to know if you’re being productive, losing money, or undercharging for something! I just started using RescueTime and we’ll see how it goes.
  • Micromanaging bosses. It’s nice not to have someone breathing down your neck, but what if you need that to be productive? Here’s a guy who paid someone on Craigslist to slap him and keep him on task. Personally, I have suddenly been blessed with incredible discipline, so I can usually wrangle myself in line to get work done, but it’s hard! It’s like arm wrestling with X-Men’s Professor Xavier in your mind! All day!
  • Budgets, budgets, and more budgets. For those of you eyeing your professional development or equipment budget with envious eyes that can’t get past the accounting person in your office, you can’t buy something fancy and awesome just because you’re your own boss now. If anything, you’re more likely to not buy things you NEED in order to keep overhead low! (Though is a wireless keyboard really a need? Come on, Sarah…)
  • Having awkward conversations. These awkward conversations used to be with coworkers, customers, and bosses (“Ah, yeah, I could do your work for you today while you go on vacation…”). Now they’re with new customers. (That is, it’s awkward for me, sometimes, to try and perform the way I want to).
  • Not getting raises. Now, this one is a little different, because whenever I want a raise I CAN work my butt off, learn a new skill, and charge more (or get more clients). But still, this is not a scenario in which I blink and suddenly get a raise for my work. You still have to put the time and effort into increasing your income. And if you don’t, it won’t increase… it may even go down!
  • Lack of career mobility. IF YOU’RE NOT CAREFUL you can replace your 9-5 grind with a freelance grind: taking customers and deposits just to pay bills and working around the clock. If you don’t stop and find purpose in what you’re doing (and take on projects and clients that mean something to you)… you’re headed nowhere!

That said, freelancing is the jam. I was going through a low period about three weeks ago because of a lot of indecision in my brain and heart. But now I’m back on track and full of hope for the future. Sometimes it takes a little “middling” to get through the uncertain parts of life, but if you’re lucky you can turn the ship around before it sinks too low.

Holler back freelancers: what else did you think you were escaping only to face HEAD ON as a freelancer?

Or, conversely:

What do you want to escape from your FT job and I’ll make a joke about how freelancing has that, too!

P.S. And if you just like sharing about freelancing… maybe you should hop over to my recently released eBook: the Five Figure Writer! Choc full of the HOWS and WHYS I used to replace my full time income working a bit less than full time… because who doesn’t want to do that?