TAKING YOUR BUSINESS BACK TO SCHOOL

Spring gets all the credit for new beginnings, but fall is the season of change. If you think back to that “first day of school” feeling from your youth, you’ll notice all the ways it has followed you into adulthood with every fresh challenge and clean slate. 

Fall was an opportunity to update your image, set new goals, and show off how much you’d grown as a person over the summer. As self-employed adults, the end of Q3 is an ideal time to start mapping out a new year that will be here before you know it. Think of it like picking out the perfect outfit for the first day of sophomore year: a chance to reflect on who you’ve been and who you want to be as a business owner in 2026. 

Whether you want to tackle the next growth stage or reinvent your business completely, early goal planning is the key to getting where you want to go. Sharpen a number 2 pencil and flip to the first page in a fresh composition notebook (or just download our Q3 audit worksheet), and let’s begin.

1. Update Your Offerings

If you ever studied abroad (or had your braces removed during summer vacation), you’ll recall returning to school the following September feeling like an entirely new person. Personal evolution may slow down over time, but it never stops. As a business owner, you’re constantly growing and changing. The types of projects that used to completely fulfill you may start to feel like a slog — and that’s ok. 

Break out the books and take an objective look at which service offerings have performed well and which may be weighing you down. Reviewing this year’s invoices will give you a bird’s-eye view of how you spent your time as well as an opportunity to reflect on how you felt about it. 

Identify the work that was gratifying, interesting, and fairly valued, and focus on how to attract more of the same. You can’t always control the kinds of opportunities that show up, but you can control what you target and pursue. 

2. Assess Your Rates 

For many freelancers, money conversations are the hardest part of self-employment. While we can’t make generational financial shame and awkwardness disappear overnight, we can attest to the benefits of notifying clients of rate updates in advance. 

If you’ve deepened your expertise through experience or training over the past year (or you simply need to keep up with the rising cost of living), changes to your rates or pricing strategy are probably in order. Calculate your margins and stand by your numbers. Announcing next year’s rates in September gives your clients the duration of Q4 to respond, and you plenty of time to nurture new leads if anyone decides not to renew their contract at the new rate. 

3. Take Some Electives 

As a solopreneur, you don’t need anyone’s permission to pursue things that capture your interest. If you’re a copywriter who’s a secret Photoshop wiz or a designer with a knack for catchy slogans, nothing prevents you from veering outside of your lane and developing skills that may not necessarily relate to your core business offerings.

Sign up for that online graphic design class or take a creative writing course at your local community college — even if it doesn’t lead to a monetizable skill, having multiple creative outlets will make you a more agile thinker and better problem solver. 

4. Clean Out Your Mental Locker

It’s hard to find the right mix of work, rest, and fun if your life is bursting at the seams. As you approach the maximum amount of work achievable by one human, you’ll have to make tradeoffs to maintain a good quality of life.

Just like your high school self couldn’t play two Fall sports, edit the yearbook, and lead the Quiz Bowl team to victory without losing your mind, your business-owner self can’t say yes to every opportunity that comes your way. 

A huge part of doing the work that really matters is saying no to the work that’s better off being done by other people. This may look like hiring other professionals to help with administrative tasks, taking on subcontractors, or passing projects along to the right colleague. FOMO is a beast, but long-term business growth requires solopreneurs to be selective and comfortable delegating the tasks that weigh them down. 

5. Let Failure Happen

Not every new strategy, scheme, and idea will pay off right away — and some never pay off at all. Much like that time you tried to get all the kids in your homeroom to call you by a cool nickname, sometimes you just have to let things go. 

Your business exists in a constantly-changing matrix of industry trends, technological developments, personal preferences, and operational needs, so the refining process is naturally eternal. If you require instant success to feel confident in your business, you’ll miss out on the best parts of being a solopreneur. 

Unfortunately, the best way to get comfortable with failure is to practice failing. Taking on manageable risks and evaluating the results with an attitude of curiosity will slowly dismantle the core belief that you must maintain a 4.0 in self-employment in order to be valid. 

If your obsession with perfection has been holding you back from useful experimentation with your schedule, pricing strategy, or business model, look for ways to practice being a little uncomfortable in the coming year. It’s the only way to learn something about yourself that you didn’t already know.