When really is the best time to start a business?

You’ll hear plenty of influencers urging you to "chase your dreams, start a business today, and never look back!" But let’s be honest: Every person’s situation is unique.

Success isn’t just about having a great idea or passion. It’s about timing, circumstance, and risk tolerance.
You probably shouldn’t throw your life savings into a startup when you’ve got a mortgage, a baby, and a second on the way. Nor should you risk your savings when you’re three years from retirement.

So, should you actually start a business?
Here are my top three reasons to start—or not to start—a business.

When to Start a Business

1. When you can afford to go broke and bounce back
Being 23 and living with your parents isn’t glamorous, but it’s also a golden opportunity.
If your business fails, you can pick up a regular job, and start over. You’ve got time on your side, minimal obligations, and hopefully parents who like you enough to let you hang around a little longer.
Risk is relative. If you can afford to take big swings, go for it.

2. When you’ve got a team
Going solo might mean keeping all the equity, but it also means carrying all the pressure.
A good founding team can pool together more money, provide unique skills and more people to help skyrocket a new business.
Complementary skills, shared vision, and mutual accountability increase your odds of success, and significantly reduce the risk of going insane alone in your living room.

3. When your last business succeeded
Success breeds confidence and credibility. If you’ve already launched and grown a business, your chances of doing it again are far better than average.
That said, don’t get cocky. Just because your last venture succeeded doesn’t mean the next one will.
Stay humble, apply the same principles, and remember: what worked before might need tweaking in a new market.

When NOT to Start a Business

1. When other people depend on your income
If you’ve got a family to support, your priority isn’t building a business empire. It’s building security.
Betting your entire household’s future on a startup is not brave. It’s reckless.
Instead, consider starting small. Side hustles, freelance gigs, or low-investment ventures you can develop after hours allow you to build something, while still paying the bills.
Worst case? You lose some time. Best case? You create something real, without risking everything.

2. When you’re older, wealthier, and enjoying life
If you’ve already built a comfortable life and are nearing retirement, ask yourself: what are you really chasing?
Will an extra €500k really improve your quality of life more than the peace of mind you already have?
That doesn’t mean you shouldn’t start a business. But lean toward projects that are scalable and sustainable. Think: real estate, an online business, consulting, or mentoring.
Choose something that excites you without threatening your hard-earned retirement.

3. When you can’t handle the risks
Let’s stop glamorizing the entrepreneurial grind for a moment.
Yes, being your own boss sounds great. Until you receive your tax bill, a client ghosts you, and you realize your pension is not guaranteed.
Entrepreneurship means uncertainty, pressure, and often long hours. If the idea of inconsistent income or late-night problem-solving terrifies you, that’s OK.
There’s nothing wrong with earning a stable paycheck and switching off at 5 p.m.
Freedom comes in many forms. Sometimes, a reliable job is the smart, brave, and admirable choice.

Thinking of starting your own business or finally getting your finances in shape so you can live the life you want?
Let me help you.
Click on the Get Started button to schedule your free consultation.

Because it’s not what you make. It’s what you keep.