People often ask me how I found the courage to quit my job and start my own business. A lot of those people assume I had everything figured out when I quit. Nothing could be further from the truth. I started my business with zero customers, zero products, and only a vague idea. I made the leap into a very uncertain future yet somehow it didn’t seem that crazy at the time. You see I knew in my heart that I needed to be my own boss. 

I’ve been self employed now for 31 years and counting. In fact I often joke that I am chronically unemployable. Mostly because the thought of working for someone else makes me want to throw up. But make no mistake the life of an entrepreneur is not a fit for everyone. A lot of people make the leap telling themselves that it is a lifestyle that they want. In many cases, people are attracted to the freedom and independence, but fail to take into account the key attributes of successful entrepreneurs.

Today I want to share with you 5 signs that you may be ready to be your own boss. 

You’ve Got An Idea Stuck In Your Head

You either know what I’m talking about or you don’t. In my case, my idea was to use my knowledge and experience with educational technologies to create a business. But that wasn’t all. I also wanted to move from the city to a small fishing village in Nova Scotia Canada. At the time this little hamlet was a four hour drive from the nearest city or airport. People said I was crazy, but I couldn’t stop thinking about it. Night after night I’d wake up listening to duelling voices in my head. One voice kept telling me to get on with it, pointing out that I was miserable stuck in a job that took so much of my time (my two young children barely saw me) where no matter how hard I worked, it was never enough for my boss. Then my own personal Debbie Downer  would chime in, “Are you crazy. Only an idiot walks away from the security of a six figure job to start a business in the middle of nowhere. What’s wrong with you?” 

This battle royale in my head went on for months (in truth probably for more than a year). I tried to put the idea behind me. On occasion I would think that it was gone, then it was back. “Hello again. This is your 3:00 am wake up call. Now about that business…”

If you can relate to any of this, I have good news and bad news. The good news is that you’ve stumbled upon something that  you really want to do. If it wasn’t something you really wanted, you wouldn’t keep thinking about it. The bad news is that there is only one way to make this fear go away. You have to confront your fears head on. It’s either that or you can join the masses of people who have opted out, choosing to accept that some dreams are unattainable. After a while, they forget how to dream. Having an idea for a business stuck to your brain like velcro is a good indicator that you may be ready to be your own boss.

You Hate Following The Crowd

The next time you’re on an airplane, an underground subway, or even at a sporting event, I encourage you to take a good look at the faces around you. How many are truly happy? The subtle hints are everywhere. Smiles that seem a little too forced, eyes that have lost their sparkle. Odds are that many of those faces belong to people counting down the days until retirement, even if retirement is 15-20 years away. Others have resigned themselves to the idea that this is just what life is all about. Both groups of people have one thing in common. They go where the crowd goes. 

I was never that guy. I’ve been defying conventional wisdom my entire life. In high school I revelled in taking opposing opinions in debates. Just for the fun of it. At university I chose to study history even though I had no intention of pursuing a career in teaching (pretty much the only place I could utilize the specific knowledge I was learning). After I got married, I moved, not once, but two times from a big city to a tiny fishing village. Things didn’t work out the first time, but it didn’t stop me from trying again. I’m still a lot like that today. I cringe whenever someone says something like “that’s the way we’ve always done it” implying that this should never change. The truth is if I’m in a crowd and everyone starts to go to the right, I instinctively look to the left. Over the years I’ve spoken to thousands of fellow entrepreneurs. The successful ones all have one thing in common. We never follow the crowd. It bores us.

You Crave Independence

This is another attribute you’ll find in just about every entrepreneur. We don’t like being told what to do. We need (not want) to control our own schedule, and place a huge value on choosing what we do and who we work with. Here’s the thing. Craving independence also means taking responsibility for everything that happens in your life. You’re the one making the decisions and you’re the one who owns the consequences. Good or bad. A lot of people find this difficult to do. 

Independence also means being able to deal with uncertain outcomes. 

None of that mattered to me. The desire to be my own boss overpowered any of those concerns. But don’t kid yourself. Craving independence and getting independence are two different things. 

You’re Willing To Defer Gratification

I wish more people would talk about this. If you’re the kind of person that needs instant gratification do not start your own business. You’re going to fail miserably. The desire for instant gratification is going to hurt you in so many ways. You’re decision making will be focused on the short term. The end result is almost always a business with a shaky foundation and little focus. You’ll likely fall into the trap of chasing short term opportunities. You just can’t make it work if you’re looking for instant gratification.

I scaled my side hustle to $10 million in sales. That would never have happened if I hadn’t been prepared to invest in the business as it grew. People always focus on a business’s ability to make money (rightfully so). But please remember a business also consumes money. It’s the fuel that keeps the business running.

Success in business requires a high sense of urgency with a laser focus on the long term. That means that you have to be willing to defer gratification.

You Place More Value On Time Than Money

This one drives me crazy. Just about everyday I speak with someone that has recently made the decision to start their own business. In almost every case, the reasons they give me have more to do with family and freedom than they do with money. In other words, time is more important than money. It’s not that money isn’t important, it’s just that spending more time with the family has a higher value to them. In my case this was easily the biggest reason I quit my 6-figure job. So I get it.

Then I start asking questions about the current state of their business and guess what?  I’d venture to say that 95% of the early stage business owners I speak with are actually putting a higher value on money than time. An experienced entrepreneur can spot problems in a new business in very little time. Starting a new business is easy these days. All you need is a brain and a computer. Growing a business takes time and money. Most new business owners find themselves putting in insane amounts of time while starving the business of money. They spend money only when necessary, and when they do they often spend money in the wrong places. 

This is why so many business owners find themselves stuck on a treadmill (or as one recent post on LinkedIn suggested running around like a rodent on a hamster wheel). They believe in their heart that all they have to do is tough it out. Time, which at one point was their motivation for starting their own business, is the one and only resource they throw at their business. This is a problem. Assuming that elapsed time will magically result in improved financial performance is dumb. It rarely works. This is why so many small businesses fail to reach their true potential, or simply fail. 

The truth is most new business owners would rather work long hours for low pay for as long as it takes, than pay for a business coach/mentor that can save them time and, ironically, money. 

I don’t expect this article to change that. But if you haven’t yet made the jump to self employment, then I implore you to acknowledge that you don’t know what you don’t know. The truth is that almost every successful entrepreneur I’ve met places a higher value on time, than they do on money.

Tim Alison is the Host of The Screw the Naysayers Podcast. He also advises and mentors experienced leaders on how to create and scale a business built around an idea or skill. Feel free to contact or on his website

Tim Alison

Tim Alison

Business Mentor, Harvard Speaker, Magnify You Facilitator, Author x 3, Podcast Host at Screw the Naysayers

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