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The Key Question Driving Entrepreneurial Success

Steve Jobs had it right – the only way to find success and happiness in your career is to do what you love. Take a good look at that wooden prototype he and Steve Wozniak built back in 1976. It may not look like the sleek models we use today, but you can see the vision behind it. If you look closely, you can see that they asked themselves the one crucial question that all successful entrepreneurs ask themselves. And planning for entrepreneurial success is all about asking the right questions.



Entrepreneurship is not for everyone. It’s a risky business and entrepreneurs are risk-takers. But, you reap big rewards for your ventures. Yes, it takes courage, and a lot of it, to become a successful businessperson. But more importantly, it takes strategic planning. In other words, you need a clear roadmap to get you where you want to be.

Running a business is like navigating unfamiliar terrain. Without a map having clear directions, you’ll soon find yourself lost in a never-ending maze costing you not only hundreds of thousands of dollars, but time and emotional distress. From the outside, it might all seem smooth sailing, especially for those of you who are starting out. But trust me, it’s not.

Entrepreneurs have a lot on their plate. All my executive coaching clients face problems that go way beyond how to operate their business, or how to hit that 7-figure or 8-figure in annual revenue. More often than not, our discussions lead us to deeper philosophical and experiential topics.


All successful entrepreneurs are strategic thinkers. And being a strategic thinker involves much more than asking questions about your business model, how much revenue you want to be making in the next 6 months, or even where you see your business in the next 5 years.

It involves being aware of your priorities. And since your priorities are rooted in your values, it means being aware of your values too.

All priorities are not equal when it comes to entrepreneurial success. It will become clear to you after some deep reflections – no two goals are the same. And I am not talking about monetary goals. I am talking about prioritizing your career purpose.

Goals and priorities, as we are about to see in this post, are not equal. Some are more important than others. This realization will help you avoid the countless minutes, hours, days, months, and probably years of prolonged anxiety, stress, depression, troubled relations with your loved ones, and being disappointed, frustrated or angry with yourself.

Learn to differentiate the noise from what really matters. The top 5% of entrepreneurs have this ability. They always get their highest priority straight, and they know what they want in their life and they know how to get there. I know this to be true because I have been helping leaders do exactly that – figure out their most important priority in life and execute it. That’s why leadership coaching exists. And it might be surprising for you to learn that the question of money rarely comes up in our sessions – because money targets alone are counter-intuitive.

But come on, Cobey, isn’t money the whole point?

No, it is not.


You need to make money. I get that. You need to ensure your survival. And you want to get the things and life you desire. How much money you need to do that will depend on you because money is relative to each person.

Entrepreneurs would often say they want to make at least in the millions to live the life they desire–to be happy. However, when asked how they came to that conclusion, they are usually lost for a concrete reason. They don’t know how much they want or what they want for that matter.


Let’s say you have a figure in mind. You have done your math. First, you need to ensure your survival. You know how much you need to pay rent, food, bills. Once you’ve done that, you can take your business to the next level, and to the next.

You know how much you need to secure financial independence. It might be getting the things you have always wanted, or doing the things you have always wanted to do. And this is important.

Everything has a price when it comes to entrepreneurial success.

You have to know what you want and what price you are willing to pay for it; and you have to know this beforehand to avoid running into trouble later. How much do you want to be making? A 7-figure income? That’s great. How much are you willing to pay in hours, days, months, years? Are you willing to work 10 hour days, 5 or 6 days a week, or is that too much? Hell, people like Elon Musk work 16 hours a day. They love their work so much. They’re driven by their purpose.

How bad do you want it? That will depend on your purpose. What’s the thing that drives you? Yes, you set out to make money, everyone does, but there has to be more to it. Your purpose will give you an edge. It will make your business unique because you’ll be an original. An innovator. Just take a look at all the big brands in the world. What makes them so special and popular?


Top entrepreneurs are driven by purpose. It’s the fuel that powers their life and business. And it’s not money. Money is a by-product of their purpose. The founders of all the big companies and brands set out to build something great and unique.

Your purpose is the foundation of your life and business and it will determine your priority. It will give you the insight and originality to build something unique and great that will stand the test of time. I can’t stress this enough. It’s one of the most important things I discuss with my executive coaching clients. What drives you?

Get this right and it will simplify your life, because life is complex. Our great ancestors from the times of antiquity had it all black and white, but in our day, it’s a hundred shades of gray in between.

Think of it like this:

We entrepreneurs are hunters. We go out and hunt for food. When our great ancestors lived on planet Earth, if you were the head of the family, you had two options: option A—you go out, hunt, and bring back food to eat. Or option B—you die either from hunger, an uninvited lion, or members of a rival tribe. It was fairly black and white back then: live or die. No one had the time to ask the deeper existential questions like How can I gather the courage to escape this 9-5 job and finally build the life I have always dreamt of? How do I make more time for my family and myself? Why don’t I feel satisfied with my life? What’s my purpose?

But we are not living in 1000 BC anymore. The world has advanced, and life has evolved to be much more complex. It’s a series of relationships: study, work, family, career, love, happiness, priorities, and philosophical questions like what’s my purpose.

Not black and white at all. Life satisfaction levels have dropped because we have so many conflicting goals, ambitions, tasks on our to-do lists that, somewhere along the way, we forget our priorities.

So what do we do?

We figure out our single most important priority and it will sort out not only our business decisions, but our life decisions as well. We become a strategic thinker and planner, and we think like the elite group of high performers and empire builders.


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. -Steve Jobs

Steve nailed his priority. It was his purpose. He lived to build great things, and he was a leader and innovator at heart.


But everyone is unique. No two people are exactly alike. People have different values, and so, different goals and priorities in life. So how to find your “great work”?

It’s a process I explain to all my entrepreneurial success clients.

Ask yourself this: what’s the one thing you’ve always wanted to do at some point in your life? It must be one thing. The thing you’ve dreamt of doing. It’s what keeps you up at night. Your biggest someday goal. What is it? It will be one priority, not two or three. One.

Does something other than money come to mind?

Let’s assume you overlook this part and set your money goals first. You don’t know what your one most important priority is but you do know you want to make money. Sam is making $XX million a year, so you want to make that amount too. You have to get everything you desire.

You work day and night and despite all the fears and failures, you hit that mark. You can now afford the luxuries life has to offer. You can have what Sam has.

You get that new car and you feel so happy. Fast forward three months, your feelings begin to normalize. The happiness high eventually comes to its baseline. You drive the same car you always desired to have, but you have the same worrisome thoughts you had when you were starting out with your business.


We all usually have the wrong ideas about happiness. If you head down this road, pursuing happiness by acquiring things, it will lead you to an endless cycle of chasing your own tail.

So what do you do?

Purpose, remember? What’s the thing that drives you, gives you the courage and motivation to do something extraordinary, to think big? This idea will give you the motivation to work countless hours, days, nights to build something great. And time is a far more precious currency than money. We should invest it wisely.

Steve Jobs knew exactly what he wanted. His passion drove him to heights no one had seen in his day. The iPod and the iPhone disrupted and monopolized the market. Your one priority will ignite your passion. It will give wings to your imagination and bring new ideas into your mind.

If passion fuels your business, you will never have to worry about having a midlife crisis halfway through the journey. Your one priority will give your life a purpose and renewed vigor.

Life is too short to waste on things that don’t serve your purpose, or worse, take you far away from it, blinding your vision. Once you zero in on your purpose, you will get renewed motivation, and a holistic way of looking at your life.

Find your purpose. It’s your North Star. Live it in your life and career. It will lead you to heights you haven’t yet imagined.

Interested in learning more about how you can identify your purpose? Click here.


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