True Success is Elusive

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One of the common interview questions early in my career was “where do you see yourself in 5 years?”. I felt like a fraud every time I answered that question. I came up with an answer, of course. I knew having no plan wouldn’t reflect very well on me. But the truth was I didn’t have a clear picture of where I would be five years down the road. I made up an answer that seemed reasonable based on the job I was interviewing for.

If you were to ask me today, I have an answer. I have a clear picture of where I’m headed, what success looks like for me in the next five years. But even with a clear answer at the ready, I don’t always feel confident in my direction. I second-guess myself, wondering if that’s really where I want to go. Sometimes I even change the picture, heading in a slightly different direction. I find it challenging to make a five-year plan and stick to it.

Across the hundreds of smart successful people I’ve met, I have gained some comfort knowing that I’m not alone in this challenge of knowing what’s next. Far from it, in fact. The majority of high achievers find themselves in a similar place.

If you have pursued achievement your whole life, you may be able to relate. It can be hard to know what comes next. You don’t know what opportunities will come your way, and you may not be sure how far and how fast you can go. You may have moved up your career faster than others around you, but how far will that take you?

When I started at Apple, I was told that most people take six months to ramp up at the company. I thought that was ridiculous. It had never taken me six months to ramp up at anything. I took it as a personal challenge: I would be faster than that. When I finally picked my head up, comfortable with my job, the extended team, and how to operate effectively, it had been six months. If I’m honest I was humbled by that experience. Externally I was recognized and given more responsibility—even after just six months—but internally I was shocked. I challenged myself but I didn’t exceed the target.

My learning curve at Apple took me longer than I expected, but I went on to be successful. After a few years I was promoted to Director of Finance. I had arrived, and I felt proud.

The problem was that I didn’t have another career goal beyond that. I had no desire to climb the ladder any further. From that point on, there was no five-year plan. And without another target to achieve, I began to question what was next for me. Having spent my entire life—in school and professionally—climbing the ladder, I suddenly had nowhere else to go. As nebulous as my five-year plan was when I began my career, my future was now totally opaque.

My choices seemed to be staying at my current job indefinitely or making a lateral move. They both had downsides. Staying for another 10-15 years in my current role meant the risk of becoming a work zombie—showing up for work each day, mindlessly going through the motions with no passion or heart, waiting for retirement. The other option would be a lateral move. It could be exciting to learn something new, but did I really want to pour my energy into starting again? Was that really what I wanted?

That was the question that stumped me: what do I want. I simply didn’t know the answer.

The problem is that high achievers have been awarded and recognized for being smart, delivering on what is asked, thinking through all the angles, getting the right answer. That mindset assumes that there is a right answer and that if you think hard enough you’ll find it. And those two assumptions are what prevent these bright people from knowing what they want. It’s why they get stuck in the A Trap, trying to think their way to the right answer about what’s next, what their five-year plan is. But you can’t think your way to a right answer.

Most people want a good life. They want to be happy, they want to learn and grow, they want to enjoy time with friends and family, and they want financial security. The challenge is how to have all of these things at once. Nearly everyone will tell you that you can’t have it all—you have to sacrifice. Work hard now, and you’ll have freedom later. Save money now and once you achieve financial independence you can do whatever you want.

Those are rational arguments. They make sense. You would win a debate contest with them. But they aren’t true. They are the beliefs that stand between you and knowing what you want. You have to relax those beliefs and get creative. If you’re confused or uncertain, you can be sure that you’re holding yourself back.

As a high achiever, you’ve been trained your whole life to be rational and practical, to do what’s asked of you, to excel and achieve your goals. But you can’t find what makes you happy by being rational and practical.

Joy, laughter, contentment, intimacy… these words describe a good life, but they aren’t rational principles. They are the language of the heart. If you want to find what makes you happy, you have to listen more to your heart than to your head.

You may find yourself in an internal debate, with your rational self arguing for the safe and practical approach (stay on this path, keep going, you’ll reach financial independence in 10 years and then you can do what you want). The other side will argue to go for what you want right now. If you are happy now, you won’t be focused on retirement as the gateway to freedom because you already are free. Life is short, why not pursue your dreams?

Confronted with this argument, you face a simple choice. Play it safe, or go for the life you want. It may be a simple choice, but it feels like abandoning everything you’ve worked so hard for. You’re voting with your heart for a good life while your rational brain, the one that has brought you so far in life, is telling you to stick it out with the tried and true path. No wonder you get stuck.

Here’s what I’ve learned about the five year plan. You don’t have to have the right answer. You don’t even have to be 100% confident in it all the time. But you have to have a plan that comes from your heart, and you have to pursue it. When you’re moving forward, step by step, you learn what you like, and you are happy because you’re making progress. You begin to believe that you really can have a great life right now, without waiting for retirement.

You can’t create a good life rationally, and you won’t decide for a good life from your rational, cautious, high achiever mentality. Rationality does not lead to passion. If you want a good life full of joy, laughter, connection, and meaning, you have to listen to your heart. Trust that it will work out, and follow your heart. Your future self will thank you for it.