I will always bet on myself. If you’re an entrepreneur, I bet you have the confidence to say the same.
Starting a business means putting your time, money, and reputation behind the belief that you can make something work when nobody can promise you that it will.
But that bet is only the beginning.
Entrepreneurship requires you to make hundreds of other bets on ideas, people, products, markets, and opportunities. You have to decide when to put more money into something, when you’ve put in enough, and whether disappointing results mean you need more time or need to change direction.
My husband Mark and I have started numerous businesses over the years. Some worked; others didn’t. We call the expensive mistakes “seminars” because we try to learn something from them.
After all those years and all those bets, I’ve become more savvy about what deserves a bet, how much I’m willing to put behind it, and what would cause me to change my mind.
5 Bets Worth Making
1. Bet on a Problem Actually Worth Solving
If Mark sees something that could work better, there’s a good chance he’ll have a business idea before dinner. That’s just how his mind works. I’m usually the one who takes the idea apart, looks at what it would require, and decides whether we ought to put anything behind it.
The problem with ideas is that enthusiasm doesn’t mean anybody else will care.
A lot of our businesses came about because we ran into a problem ourselves. We owned a property management company, for instance, and our marketing manager quit by text while we were on our first vacation in seven years. I’m still a little bitter about the timing.
We needed another way to get the work done. Eventually, we realized other business owners had the same problem and were desperate for a fix, so we started a new business to provide solutions.
When something is causing real pain in your own business, look around. Are other people dealing with it, too? And just how badly do they want it fixed?
I’ve seen plenty of things people complain about but aren’t willing to spend a dime to fix. I bet you have, too. That’s probably not where I want to place a big bet.
2. Bet on What You Can Prove
Entrepreneurs have to take risks, but I’d rather find out what I can before putting more at stake.
If you’re considering a new service, can you sell it before investing heavily in building it? If you think you need more capacity, can one hire tell you something before you make three? Sometimes a relatively small bet can answer a question before you make a much larger one.
But at some point, when you have enough evidence, you have to be willing to act on what it’s telling you.
I didn’t do that with my corporate job.
Mark and I started our property management company in 2005. It was successful, but I didn’t leave corporate America until 2009. I liked the paycheck. It was my safety net, and I was hedging my bets.
Looking back, I think I could have left in 2006. For someone who says she will always bet on herself, I wish I had bet on myself a lot sooner!
At the time, though, I needed that security. The bet that looks obvious five years later may not have felt obvious when your own money and future were sitting on the table.
That’s something I pay more attention to today. Sometimes what you learn tells you to hold back, but sometimes you’ve seen enough to put more behind it. Don’t be scared to act in those moments.
3. Bet on Your Ability to Change Course
I’ve spent a lot of money on mistakes over the years. Hence, the expensive seminars.
But I don’t regret them. Once I make a decision, I own it. I made up my mind a long time ago that I was going to make the best decision I could with the information I had at the time and live with it.
But owning a decision doesn’t mean defending it forever.
If it turns out I was wrong, I want to figure out what I missed and what I need to change. What I don’t want to do is keep making the same mistake because I’m determined to prove the first decision was right.
That’s why it helps to know what you’re expecting before you get too far into something. Maybe it’s a revenue number, a deadline, or a performance expectation. If you’re not getting there, pay attention.
That doesn’t automatically mean you quit. It just means you take another look at the bet before putting more behind it.
The “seminar” only becomes really expensive if you refuse to learn anything from it.
4. Bet on the Right People
Some of the biggest bets you’ll make in business will be on people.
Hiring somebody starts with being clear about the problem you need that person to solve. What do you need them to accomplish? What does success look like? If you can’t answer those questions, you’re not ready to make the bet.
Once you have the right person in the right role, the bets continue. How much responsibility are they ready for? Over time, you may trust them with employees, customers, budgets, or decisions you once handled yourself.
I wasn’t always particularly good at that. I looked at our businesses as my babies. Nobody was going to love my baby the way I did. And, frankly, they probably weren’t. It was mine.
But I also wanted the freedom we had started these businesses to create, and eventually I had to accept something: Freedom requires that you trust other people to do the work.
I couldn’t have freedom while requiring everything important to come through me.
So, I learned to watch what people did with the responsibility we’d already given them. Did they understand what mattered? Did they use good judgment? Did they learn when something went wrong?
We’ve had people who grew tremendously when we gave them more responsibility and others who showed us they weren’t ready for more. Both told us something we needed to know.
You don’t have to hand someone everything on day one. Let them earn a bigger bet.
5. Bet on the Payoff
Before making a big bet, I want to know what I’m actually trying to win.
Entrepreneurs can get pulled toward growth simply because an opportunity is there, like another location, service, or new market. When something looks promising, it’s natural to start asking whether you can make it work.
But there’s another question worth asking: If it does work, do I actually want what comes with it?
Another million dollars in revenue sounds terrific. But if getting it requires 20 more employees, another layer of management, a large capital investment, and a lot more of your time, that’s part of the bet, too.
Mark and I have always had what we call our prime directive. For us, the goal was to get to a place where our money was working for us instead of spending our lives working for money.
We’ve had great business opportunities come along that could have made us a lot of money. We passed on some because they would have dragged us down a path that got us farther away from our prime directive.
That’s probably one of the biggest differences between how I looked at opportunity when we first became entrepreneurs and how I look at it now. Back then, I was much more likely to ask, “Can we make this work?”
Now I also ask, “What do we get if we do?”
Because you can win the bet and still end up with something you didn’t really want.
That’s why I think every major business decision has to tick the box that matters to you. Whatever brought you here, don’t get so caught up chasing opportunities that you build your way farther from it.
Sometimes the payoff justifies a big bet. Other times, you can look at a perfectly good opportunity and decide it isn’t worth what you’d have to put into it.
I will always bet on myself. I’ve just gotten a lot pickier about the other bets I make.
The question is, what deserves your next bet?
Anne Lackey is the co-founder of HireSmart Virtual Employees, a full-service HR firm helping others recruit, hire, and train top global talent. She has coached and trained hundreds of U.S. and Canadians in creating successful businesses to be more profitable and to create the lifestyle they desire. She can be reached at anne@hiresmartvirtualemployees.com or at meetwithanne.com.
Photo courtesy Alex Shuper for Unsplash+
