How I measure success as a solopreneur has evolved a bit over the last 15 years.

I’ve been running this solopreneur gig for more than 15 years now. Take a moment to let that soak in. I’ve been my own boss, managed client projects, muddled through finances and created a network. For those of you who know me personally, you know just how mind blowing that is. Organization and planning are not my strongest skills.

I’ve had to figure out a lot of stuff on my own. A short list of skills I’ve had to learn or expand on are:

  • Project Management (surprisingly not the hardest part of my job)
  • Customer Service (if you know my mantra then you know why this hasn’t always come easy to me)
  • Programming languages (gag)
  • CMS design (WordPress)
  • Marketing (both digital and traditional)
  • Consulting (people want to know stuff)
  • Finances (managing money is no freaking joke folks)
  • Photography (I always want to improve)

That’s just to name the big ones. The tangible ones. I dabbled in most of this as an in-house employee at a small agency. Until I went out on my own I had no idea how to really do any of those things proficiently enough to get paid for it. While those skills were challenging, they’re also easy to measure on the success scale. How do you measure self-confidence or self-worth? One thing that has been hardest for me to grasp has been how to measure success as a solopreneur.

When I worked in an office setting with other humans it was easy to get feedback. My boss was always critiquing and criticizing, so the things you needed to work on were obvious. Likewise, accolades from coworkers and clients were a great gauge of how well you were succeeding within the company. And then there were always added benefits and raises to let you know how you were doing.

Out here on my own it’s harder to tell when I need improvement or when I’ve nailed it. I normally work in kind of a bubble so, I don’t always get great feedback from clients. Most of them give me raving reviews or else it’s crickets. Surprisingly, it’s hard to get criticism from clients. I find they mostly want to avoid confrontation, even when you’re asking for it.

So, this all leaves me wondering. On a typical day as I click away in my peaceful basement office in front of my wall of French doors with a view of the lake … how successful have I really been? I don’t make a ton of money. As a matter of fact I “bring home” about half of what I did at the agency. Even still, a good chunk of that goes into the business. I don’t have oodles of clients all the time. I average 20-30 a year, but only a handful of them are regulars that generate most of my income.

That leaves a big question for us to answer.

How do you measure your success as a solopreneur? What, exactly is the benchmark?

To answer this question, first you have to acknowledge that the answer is subjective and dependent on each person’s experiences and values. Look at what your standards were when you started and use those as benchmarks. Have you met those goals? Look at where you want to be in five years. Do your values change? How? Are you on track to meet those goals? Now, let’s look at my business.

When I started in 2008 my goals were simple. Make enough money to buy groceries for the family and be able to plan our second child and allow me to stay at home. Three years later, I was meeting that goal and then some. I was pulling in a little cash and gave birth to our daughter. Even though I was not prepared at all for the struggle that is postpartum and being a work-at-home parent, I was able to run my business and raise an infant. Over the years her needs have changed and I’ve been able to adjust for that and scale my business accordingly.

My main goals all along have been pretty simple:

  • Contribute financially to the family
  • Be financially independent (even just hypothetically)
  • Make my own schedule
  • Work on projects that I care about
  • Be more present for my family and be able to scale up once their needs change
  • Experience less stress

Now, all but the last one have been met and continue to be met. Turns out stress just exists. But, working at home allows me to be able to refocus and step away when I am feeling overwhelmed. So, there’s that.

My income over the last years as fluctuated, quite a bit actually. I still contribute in a meaningful way, our daughter (approaching her teens) requires less “mothering” so I’ve focused on scaling a little bit. I also have the peace of mind in knowing that if I had to live on my own, I could. This is a huge thing for me to have. Knowing that I have some sort of financial stability independent of my husband has been freeing. In the beginning I would constantly stress about being tethered to someone financially. Now, I don’t worry so much about that.

I have been able to take on more clients and bigger projects. I am still able to step away and spend time with our daughter several times a week, having coffee, running errands and just spending time together. We cook together, play video games and do a lot of talking to one another. I’m a fully present parent. Well, most of the time.

I get to make my own schedule and essentially choose my clients. Plus, I get to donate some services to local organizations. I work with amazing non-profits and small businesses in South Carolina and across the country. Non-profits that change the world, businesses started and led by kids, authors, makers, influencers, dancers, bad ass business women. These are all my clients!

So, I’ve checked off everything on my list and I continue to exceed my expectations of what this thing could have been. Would I love more cash? Of course! Will I hustle and bust my ass to get it? Probably not so much. I’m not that guy. You can damn sure bet I’m not going to get down on myself for not doing that though. I have learned to measure success as a solopreneur by a different benchmark.

Aside from cash flow, how do YOU measure success as a solopreneur?


  1. Aarika Johnson December 6, 2019 at 11:33 am - Reply

    Nice lens, Heather! (Pun intended!) I really identify strongly with your main goals in business and measurements for success. Great to see this and feel better about my career path too.

    • Heather M Schiefer December 16, 2019 at 9:05 am - Reply

      Aarika! Thank you. It nice to feel validated by other professionals. As much as I avoid measuring myself against others expectations, it’s always validating to hear other professional people echo our inner voices.

  2. Zack December 6, 2019 at 6:02 pm - Reply

    Love and appreciate this insight. Directed by Aarika but stayed for myself / the additional perspective.

    Thanks for addressing this head on!

    • Heather M Schiefer December 16, 2019 at 9:06 am - Reply

      Welcome Zack! Thanks for commenting. I’m glad you found something useful here!

Leave A Comment

This site uses Akismet to reduce spam. Learn how your comment data is processed.