Top 5 Things To Know as a 50+ Entrepreneur

Know Your Numbers: There is risk in every kind of entrepreneurship. Often, you are risking money. The key to being able to map out your entrepreneurial opportunity for 2026 is understanding what you are risking in any new endeavor. If you're risking money, make sure you are being smart. Entrepreneurship can be an all-or-nothing game. It doesn't have to be, but it can be. It's good to know that right up front. You might have the best idea in the world and have the most fantastic advantages, but if you miss the market, if you are too late or too early, there msy be zero return on your investment. Please be smart about your money. Don't overextend and get into a position where you can't afford to stop.

Know Your Time: I'm sure you've heard of Murphy's law - “whatever can go wrong, will go wrong”? For entrepreneurs, there's a variation on Murphy's law that says, "Whatever can take longer than you think, will take longer than you think." So if you are involved in child/grandchild care, or older generation care, or just busy being yourself, entrepreneurship will inevitably take more time than you expect it to. Part of that is because you don't understand all the friction points before you start. The other part is when you get excited about something, you tend to think about it & act on it a lot. That takes up a lot of time. Be aware of your existing commitments and know that if you jump into entrepreneurship in 2026, you are going to be compressing your availability.

Know Your Constitution: Many years ago, I came up with a definition of entrepreneur. It's a fancy word that means, "too dumb to know when to quit." It takes a lot of persistence to be an entrepreneur. It also takes a lot of resistance to doing things the way other people think that they should be done. If you aren't already comfortable in pursuing your own path, entrepreneurship is going to be doubly rocky for you. It doesn't mean that you can't be an entrepreneur if you've never carved your own path before. But it's a whole lot easier when that is your modus operandi already.

Know Your Itty Bitty Shitty Committee: I guess that's just a vulgar way of owning the idea of "imposter syndrome." Imposter syndrome is when you feel like, "Why should I be doing this? I'm not special. I'm not brilliant. I'm not creative. I'm not overly talented." That little voice that someone once called their "itty bitty shitty committee" is going to be in your ear all the time. Even if you've already been an entrepreneur, the itty bitty shitty committee really never adjourns. So if this is your first entrepreneurial rodeo, get to know the sound of the itty bitty shitty committee and learn how to tell them to shut the fuck up because you've got more important things to do.

Know Your Support System: If you become an entrepreneur and you hire people to work with you, you've actually created a circumstance where you can often feel lonely.

If the business isn't going well, it's hard to share that with your employees because that creates fear in them. If the business is going well, you get to share that but you are the only one who likely sees the dangers ahead.

So you're going to need to find other people to talk to about this stuff. Other business owners, your family, clergy, therapy, coaches, all of those people That you know has your back. You are going to have to lean on them. It is inevitable, even if you are a lone wolf, a "I'll do it myself" sort, you still need a pack to travel with, so make sure that you identify your support system and use them.