Defining Success and Coming Up for Air

When launching a business, it’s easy to keep your head down for a long time.

Countless business owners and creatives talk about the “grind” - the endless, thankless work. The only focus is on growth and hitting higher numbers. The light on the other side seems so far away - and you’re always painfully cognizant of the work it’ll take to get there.

So you put your head down and hit the gas. Flash forward three months, six months, a year and you’re still bent over your desk, burning the midnight oil.


A few months after I started working for myself full-time, I was right smack in the middle of that cycle. Last month’s numbers were never good enough, so I kept on pushing and onboarding more clients and taking on more projects.

There’s nothing wrong with driving hard toward a goal. The thing is, without an upward glance, it’s hard to celebrate progress. “Success” becomes whatever the next checkpoint is, then the one after that. There’s always something else to do. Some other task to accomplish, another project to write, a new client to onboard. Each milestone barely registers. It’s always: What’s next?

As creatives, we can be notoriously critical of ourselves. That’s where the “what’s next” mindset comes from. We’re constantly driving, pushing forward, improving. There’s always someone more successful whose work is more insightful, whose career is more lucrative.

The flipside of that coin is never being truly satisfied with where we are. If there’s always more to do, or someone who’s doing it better, how can we celebrate what we’ve done?


Two things happened in one week that made me stop and take a look around.

The first thing that happened was when a fellow freelancer reached out to me for some advice. That’s a normal, everyday thing, right? I ask other writers for advice constantly. But it was the first time someone had asked me - the first time someone had looked at my body of work and thought, “She must have some experience I can learn from.”

Until then, I viewed myself as a novice. And I am a novice. I’ve only been doing this for less than six months. But this teeny, tiny, simple thing made me think for the first time: I can do this. I am doing this.

I realized that it sometimes takes a little outside validation for us creatives to take notice of all we’ve accomplished while our heads were down.

A few days after that, I saw a post from someone celebrating his first month with over $3,000 in revenue. And I thought, “Hey! I’ve done that!” I knew I’d done that, but it never registered as a big accomplishment until I saw someone else hit that benchmark. Watching them celebrate that as a marker of success felt revolutionary.

Those two things forced me to grind to a screeching halt. Looking around, I saw not only how far I’d come personally, but the power of our little community. Even a small community of like-minded people can serve as a check against our own hustle and self-competition. Despite the cutthroat business and art world clichés, the success of others doesn’t diminish our own success.

To me, it’s the opposite. There’s sanity in our collective mind. There’s success in our shared success.


When I was first starting out, a fellow writer gave me some advice about goal-setting. Laying out small, achievable goals is one of the best ways to stay motivated, she said. Design your goals and celebrate every small step taken toward them. In fact, celebrate the crap out of it - it’s the only way to keep yourself in check, stay motivated, and avoid burning out.

I took this advice to heart at the time - but as you can probably guess by now, I didn’t do a great job putting it into practice. I’m resolving to be better about that. If you’re like me, or maybe you’re just launching a new creative business, it’s tough to pin down realistic goals. Looking back, I wish I would’ve celebrated:

  • Converting on a cold email
  • Getting paid for a piece I would’ve done for free
  • Securing a recurring client
  • Landing my first project over $1,000

I didn’t hit pause on any of these milestones, but I’m doing it now. And the best advice I can give to those who, like me, may not have come up for air in a while, is this: Stop. Take a breath. Look at all you’ve done.

Kiera Abbamonte

Freelance writer based in Chicago. She’s written for Kissmetrics, Help Scout, and Grasshopper.

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