Solopreneur tuition? How much have you paid?

Beating yourself up about the expensive mistakes you’ve made on your path to solo business success? Here’s a way to reframe your thinking.

I recall the moment vividly. I stood in the Fall Hudson Valley sunshine with my new company brochure in hand (pre-Web days), realizing I had just thrown a boatload of money down the drain. With nauseating clarity, I saw that the high-end design firm I had hired was more interested in executing their flashy graphic style than serving my communication needs. The brochure would be almost useless.

Or another time, when I hired a consultant to help with marketing strategy, and I discovered he had minimal experience with tiny businesses on tiny budgets. More money, time, and effort out the window.

In both cases, I was new to business and didn’t know what to ask or how to articulate my business needs.

Expensive lessons. And just two of many (many!) mistakes on my solopreneur journey.

The dismay of early stumbles

Have you experienced a similar pit-in-your-stomach feeling? You wonder, Will I ever figure this all out?

You ask yourself: How much more time, energy, and, most dauntingly, money will it take before I can make my solo business a success?

Ask any solopreneur who’s been at this for a few years, and they’ll admit the early road is rocky. Stress levels are high, and money mistakes can be the most demoralizing.

I could add dozens of other stories to my list of blunders. And some are recent — although thankfully, they’re not as frequent or consequential.

Consider the mix

Worthwhile wins along the way also offset disheartening stories.

Like the time I paid about six times what an average conference costs to attend a premier high-tech event. Over three days, I had a brief 1:1 chat with Jeff Bezos (early Amazon days), shared lunch with Meg Whitman (then CEO of eBay, who told me about her “army of solopreneurs” on the site), and met Katherine Graham, the legendary editor of the Washington Post. I also made valuable business connections that have lasted for years. Yes, it was a memorable investment.

For most solopreneurs, however, the satisfaction of winning often fades from memory. It’s the pain of mistakes that lingers.

But there is a better way to reflect on these stumbles.

Reframing the equation

The mental framework that has saved my sanity through the ups and downs of solopreneurship is this:

It’s all tuition.

All the time, all the energy, all the money — it’s the tuition we pay for our early learning as a solopreneur.

It’s an investment in the business experience we glean along the way. It’s our schooling in the real-world academy of one-person businesses.

Reframing it this way lightens the mental burden and gives a new perspective on the journey.

What’s your tuition bill?

This week, I challenge you to chart the positive and disappointing outcomes of the time, energy, and money you’ve invested in your solopreneur journey.

Realize that they’ve all paid dividends. Some had immediate positive outcomes. Others taught you valuable lessons that you may not have been able to learn any other way.

Celebrate them all.

Your hard-won knowledge is more valuable than a paper degree. And you put it to use every single day as you take your solo business to new heights.

---

Learning Opportunities

The turning of the calendar page to September always brings school to mind. Here are three upcoming learning opportunities that may be of interest. (I’m an Ambassador for the first two, and the third is my latest project.)

Breakthrough Facilitation

If you make your living bringing together groups of people — as a presenter, teacher, coach, or team leader — check out Gwyn Wansbrough’s cohort-based course, Breakthrough Facilitation.

Through a mix of recorded lessons, live class sessions, and a vibrant online community, you’ll learn the exact steps and components to design and lead sessions specifically for how people are wired to learn. I took this course earlier this year, and it was one of my 2023 highlights. Gwyn is a gifted teacher and facilitator, and the group is just big enough to make valuable professional connections in an informal learning environment.

Gwyn is hosting a free Exceptional Virtual Facilitator Workshop on Thursday, September 7th, at 11 a.m. ET. Sign up to get a taste of the course and pick up some facilitation skills you can use immediately in your work.

Breakthrough Facilitation runs September 26th through October 26th. Registration closes on September 17th. Enrollment is limited to 20 participants, and the course usually sells out.

Write of Passage

Over the past three years, my expanding collection of new friends and colleagues nearly always traces back to one source: Write of Passage. This online writing school attracts intellectually curious individuals from around the world. They come together to share their ideas and improve their writing online.

Write of Passage is recognized as the gold standard of cohort-based courses. It’s a 5-week sprint that teaches you how to use the power of the Internet to share ideas and attract opportunities. The course focuses on helping students in three ways: 1) Publish quality ideas; 2) Find your people; and 3) 2x your potential.

I participated in Cohort 6 in early 2022 and twice served as a Mentor (Cohorts 9 and 10). It’s now time for Cohort 11, which will likely be the best yet.

Founder David Perrell is offering a free workshop, How to Start Writing Online, on Tuesday, September 12th, at 7 p.m. ET if you want a taste of the course content and style.

Solo Business School

This last item is a coming attraction and is the project I’ve been working on for most of 2023. There’s nothing for you to do yet. Just know it’s in the works, and I’ll share more info soon.

The snapshot? 
Get your solopreneur MBA in 3 minutes a day.

---

Thanks for being a reader!

If you know other solopreneurs who want to level up their solo businesses, do them a favor and share this newsletter.