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Here’s the Only Thing You Need to Know Before Making a Life-Changing Decision


We live in strange times. Everyone seems hell-bent on becoming an entrepreneur, but that just seems to raise more questions than answers: What’s it really like? Am I cut out for it? How do I know if the timing’s right? Should I quit my day job? Is it better to raise funding or bootstrap? What if I crash and burn? Questions, questions, questions.

If you go searching for answers, you’ll inevitably find thousands of books, blogs and articles with no shortage of opinions on what you should do and how you should do it. But you won’t find what you’re looking for. Nobody can answer those questions for you. If and when it’s time to make that fateful leap, you’ll know it. I did.

When I gave up the corporate life to do my own thing, I had no illusions about how much more or less challenging it might be. I didn’t care. I’d spent 23 years climbing that infamous ladder like some crazed corporate monkey. At that point, I knew one thing: I knew I was done. And that I would never look back.

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Sounds dramatic, doesn’t it? It definitely felt that way at the time. It felt right. And it was right. But I was wrong about not looking back. After 13 years, I’m still puzzled by the question of why I don’t miss it. Why I don’t miss the compensation. The perks. The recognition. The travel. The adrenaline.

All my adult life, I’d wanted to be a top executive. And yet, after achieving that lofty goal and living the dream for more than a decade, I gave it all up to do something I never wanted to do. That’s right. Unlike everyone you talk to these days, I never considered becoming an entrepreneur. Not once.

Crazy as it sounds, that’s what happened. Thinking back on it now, I must have known it was time to move on. It felt right. And that’s why I don’t miss the corporate life. That’s why I have no regrets. I didn’t overthink it. Instead, I listened to my gut. And that made all the difference.


Don’t get me wrong; it’s not as if there was no thinking involved. Of course I knew that I had the knowledge and experience to run a small management consulting firm. And there were also plenty of voices in my head telling me that I was nuts to give up everything I’d worked for. But in my gut, I knew it was the right call.

You may not realize this, but conscious thoughts are just the surface of what’s going on in your mind. Underneath is an ocean of submerged memories and subconscious instincts and feelings. Your gut taps into that. Everything your mind does beneath the surface of your awareness. That’s where most of “you” exists.

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You should listen to your gut; it knows more about you than your thinking mind does. Don’t just take it from me. In his 2005 Stanford University commencement speech, Steve Jobs made a pretty convincing case, as only the iconic entrepreneur could, for why you should listen to your heart (heart, gut… same thing) when determining what you do for a living:

You’ve got to find what you love. And that is as true for your work as it is for your lovers. Your work is going to fill a large part of your life, and the only way to be truly satisfied is to do what you believe is great work. And the only way to do great work is to love what you do. If you haven’t found it yet, keep looking. Don’t settle. As with all matters of the heart, you’ll know when you find it.

I’ve worked with dozens, maybe hundreds of successful startup founders and small business owners over the decades. Nearly all of them worked at corporations before starting their own gigs. And just about every one tells a similar story of ideas, partners and circumstances that all just sort of came together and felt right at the time.

When it comes to those all important matters of the heart – like who to spend your life with and what to spend your life doing – by all means, give it some thought. Ask those closest to you what they think. But quit wasting time online and overthinking it. When it comes to life’s biggest decisions, trust your gut. That’s where the answers lie.