Recently, The Wall Street Journal featured a story on “pint-sized companies.” Since the pandemic, founders are choosing to build their companies with ten or fewer employees. They’re happy to have a business that can be run profitably and sustainably on a smaller scale, that also allows them to have a life.

This article landed on the heels of a call with a former professor, who for years has been encouraging me to go bigger, especially on educating others about personal finance. He said, “You know, I think you’ve gotten it right. You’re doing meaningful work that you love, and you have balance for yourself.” 

Have I gotten it right? Is small the new scale? When we pursue small business on purpose, are we choosing to play small?

Lately, I’ve been thinking about playing small versus staying small. 

Undoubtedly, you are regularly encouraged to “play bigger.” Make that marketing investment! Hire that person! Push for scale! Don’t hide your light!  

Playing small refers to the way we feel about ourselves. It’s choosing not to do things out of a sense of unworthiness, inadequacy, or incapability, or a fear that you’ll make other people feel inadequate through your actions. You might be afraid of what will happen if you have more money or power. And yes, these are real limiting beliefs that nearly everyone has.

But what if you’ve faced those things and a small business is what you want?

America loves the mythology of the struggling small business owner. And it’s true in many cases. People start businesses all the time without thinking through what it will take to be profitable and pay themselves. At the same time, there are plenty of thriving, intentionally small companies. It’s perfectly okay to design, build, and run a business that you’re not going to try to grow as big as possible if that is what you want. 

Here’s a personal example. I lived my whole life in the same town of fewer than 1,000 people. Over the fears, objections, and “you sure think a lot of yourself” sentiments, I left to attend a top college in Chicago. I moved to New York to work in finance. I moved back to Chicago and invested a gigantic gob of money into grad school. I moved to California, first San Francisco, and when I didn’t like it, to LA. When I was 7 months pregnant, I left a COO job and started my own company. Four years ago this week, I walked away from my house, most of my possessions, and a big chunk of money to leave an emotionally and financially abusive marriage.

Do I play small? Do I accept less to protect others’ feelings? Yes, I succumb to this at times. There are moments when I realize I’m playing small or being asked to accept less. It might take a minute, but I will make a change, and I will follow up with another big bet on myself.

So what’s up with my company? Why, after nine years, am I still small? 

At least once a year, I consider how I would scale. Each fall, I take a day to think blue sky about the company. I model out growth scenarios. I evaluate how much cash it will take to finance the growth, and how much more I’ll need to work. And I decide whether that’s what I want for my life. Is this the right thing to do now? 

So far, the answer has been no. At the moment, I am unwilling to take a pay cut and miss out on time with my kiddo, family, and friends for two or three years. And I know that I can’t just get a little bit bigger. The next level requires a substantial jump in revenue, staff, and infrastructure. 

For now, I am choosing to optimize for paying myself, operating in alignment with my values, and having the life I want. I challenge myself to find ways to grow that fit with my goals, not anyone else’s vision.

My way of playing bigger is to reach more people. That doesn’t mean we need more 1:1 clients. That can be growing the reach of this newsletter, supporting civic engagement, or investing in other people’s businesses. 

So, how about you? Are you small because you’re playing small, or you’re choosing small? If you’re denying your ambitions, your business isn’t working for you, or you have a different vision for the company you want to run, then let’s get to work on that. If you don’t know how to make a profit or pay yourself from the business you have, start gathering the support you need to figure it out.

But don’t build someone else’s idea of success in order to prove that you play big. Choose for yourself.

In about three weeks, voter registration starts closing. Eighteen states have deadlines during the first week of October. Use vote.org to check your registration prior to your state’s deadline. 

If you’re in these seven states, you’ll need to allow time to register in person. If you live in Arizona and want to vote in state and local elections, you may be required to update proof of citizenship prior to the registration deadline.

Voter fraud is exceedingly rare. However, about 35% of eligible US citizens just don’t participate. When asked by Pew, 62% of unregistered voters said they haven’t registered because they have NEVER BEEN ASKED. 

So, I’m asking you. And I’m asking you to ask other people. Please register to vote. Sign up for election reminders, including when early voting opens in your area. Make a plan now to return a ballot or vote in person on or before November 5.

September AMA Replay

Thanks to everyone who joined September’s AMA! We covered hidden costs to hiring employees, insurance coverage for services businesses, basics of budgeting, and mortgages for the self-employed. Check out the replay on YouTube. The topics are time stamped in the video description for easy reference.

Our next AMA is Wednesday, October 9 at 10 AM Pacific. 

Have a question for the AMA? Submit it here. Use this link to add the details to your calendar.

Media Kit 

Bloomberg: In the market for a new electric vehicle? Bloomberg reports that 3-year leases for new EVs may be had for as low as $20 a month after applicable federal credits. It’s more straightforward to write off the cost of a vehicle lease than a purchase, which is why many tax advisers recommend leasing for business owners. If you eventually want to buy the car, check the fine print in your lease for a buyout scenario.

All the finance rags: In late 2017, the Tax Cuts and Jobs Act took effect, doubling of the “death tax” exemption from $7 million to $14 million. The TCJA is scheduled to expire at the end of 2025. If you have these kinds of assets, consider estate planning moves now if you care to lock in the TCJA provisions. Here’s a helpful report from Northern Trust. 

CNN: Are you seeing the term “founder mode” everywhere this week? It’s the latest Silicon Valley VC debate on how founders should run early-stage companies. What do you think? How long is it healthy to micromanage all aspects of your business? Does founder mode apply to self-funded companies? 

FX: Need some comic relief? I’ve been enjoying FX’s The English Teacher, about Millennial teachers trying to navigate parent and kid social demands in a suburban Austin school. Four episodes are out now, available on Hulu (or Disney Plus outside the US).