Building a successful business is exhilarating, but it’s also filled with decisions that can make or break your long-term success. After working with dozens of millennial business owners, I’ve noticed patterns in the regrets they share—mistakes that were often costly but sometimes avoidable.
The good news? If you’re reading this, you still have time to make adjustments. Here are the five biggest regrets I hear from business owners, and how you can take steps to avoid them.
1. Cash Flow Issues (Too Little, Then Too Much)
The Regret: “I wish I had understood cash flow better from the beginning.”
Here’s the irony: The #1 reason businesses fail is running out of money, yet many successful business owners end up holding way too much cash.
In the early years, cash is crucial. You’ll likely face expenses you didn’t anticipate, such as:
- Higher taxes as a self-employed individual
- Unexpected business emergencies
- Heavy reinvestment needs to grow
- Hiring costs when you’re ready to scale
- Slow periods that test your resilience
But here’s where it gets interesting. Once you’ve built a solid foundation—consistent customers, an ongoing pipeline, a diverse client base, and an established reputation—holding excessive cash becomes inefficient.
What to do instead: Build a cash cushion that makes sense for your business stage. Early on, we suggest you aim for 6-12 months of expenses. As you mature, reassessing and adjusting may be required. It’s possible that excess cash could be working harder in investments, retirement accounts, or strategic business growth rather than sitting in a low-yield savings account.
2. Timing Your First Hire Wrong (Too Early or Too Late)
The Regret: “I either hired too soon and crushed my margins, or waited too long and became a bottleneck.”
I see this one playing out in two ways:
Hiring too early has potential to destroy your profitability. When you don’t understand your true capacity or haven’t maximized your own productivity, adding to payroll can create financial stress and make growth challenging.
Hiring too late can be equally damaging. Some business owners love being in control of everything, but this can create a ceiling on growth. You may become the bottleneck, working longer hours while your business stagnates.
What to do instead: Try to understand your true capacity first. Track your time for a few weeks and identify tasks that:
- Don’t require your specific expertise
- Could be done better by someone else
- Are preventing you from focusing on high-value activities
When these tasks consistently fill 15-20 hours of your week and you have the cash flow to support it, it may be time to hire.
3. Not Considering Tax Exposure
The Regret: “I had no system for managing taxes and it cost me thousands.”
As a business owner, taxes can become a much bigger part of your financial life. Your income will often fluctuate, which means your tax liability will too. Without a system, you may be overpaying (losing cash flow) or underpaying (facing penalties and stress).
What successful business owners often do:
- Set up a system for estimating quarterly taxes
- Make timely payments to avoid penalties
- Work with a proactive accountant, not just someone who files returns
- Implement tax planning strategies to help reduce lifetime liability
- Keep detailed records throughout the year, not just at tax time
What to do instead: Try treating tax management as a core business function, not an annual exercise. We suggest setting aside a percentage of revenue each month for taxes, and reviewing your strategy quarterly with your accountant.
4. Not Having a Risk Management Strategy
The Regret: “I thought I was too small to worry about liability until something happened.”
Running a business exposes you to risks you never faced as an employee. For example:
- Professional liability
- Property damage
- Customer complaints and lawsuits
- Partnership disputes
- Personal financial exposure
The tools you may want to consider:
- Business insurance: General liability, professional liability, and property coverage
- Legal documents: Service contracts with customers, employment agreements, etc.
- Partnership agreements: Often overlooked but often helpful—what happens if a partner dies, becomes disabled, or you have a major disagreement?
- Business structure: Is the business separated from your personal liability?
What to do instead: Consider working with an attorney and insurance professional to audit your risks. Yes, it costs money upfront, but it’s generally less expensive than dealing with unprotected risks later.
5. Losing Sight of Why You Started
The Regret: “I built a successful business but sacrificed everything else that mattered.”
I’m not a believer in perfect work-life balance—I think there are seasons for everything. But I do believe you need to make time for what’s truly important to you.
You likely started your business for freedom and family, not to become a prisoner to it. Yet many business owners get so focused on growth that they forget their original “why.”
What to consider doing instead:
- Set clear boundaries around family time
- Invest financially in your business AND your family
- Remember that people are what matter most
- Create systems that allow the business to run without you occasionally
- Regular self-check-ins: Am I building the life I want, or just a successful business?
The Bottom Line
These regrets are common, but they’re not inevitable. The key is trying to be intentional about each area before problems arise.
If you’re a millennial business owner navigating some of these challenges, you don’t have to figure it out alone. Working with professionals who understand the unique complexities of business ownership can help you avoid these costly mistakes so you can build both a successful business and the life you want.
Remember: The goal isn’t just to build a profitable business. It’s to create the freedom and security that motivated you to become an entrepreneur in the first place.
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