Choice as the enemy of ambition

Counterintuitive advice on how to find meaning through work

Too many ambitious people waste years trying to figure out what to do with their lives. It’s hard to blame them. Our brains have been trained by technology to continuously look for something better, creating an ingrained sense that our options are limitless.

This feeling of endless choice extends to the professional sphere where optionality has become a cruel master. Like endlessly scrolling through Netflix only to turn off the TV from exhaustion, there exists an overwhelming feeling in the hearts of many that there are too many things that they could do. Decision fatigue is real. It becomes easier to dream about potential instead of doing something and risking disappointment.

When we look for guidance, we’re told to find our why. But how can you find meaning if you don’t know what to do? Talk about putting the cart before the horse.

Endless Choice - DALL-E

“Do I start a company? Do I get an MBA? Maybe I should be a lawyer…it’s not too late for law school, right? But what will other people think? What if I don’t like being a lawyer?”

We all know someone like this. In fact, I was this person early in my career. My mind filled with wildly competing visions of being an Important Person in private equity and a <<< Founder >>> of an e-commerce brand. Not because I was fired up about due diligence or into digital marketing, but because in our perceived world of endless choice, they both sounded like lofty things I should want to do.

We can all feel it. There is an undercurrent in the professional ether that a person of even modest ambition cannot simply pursue a career. They must feel called to do something greater than themselves.

For example, working in the healthcare industry can no longer just mean providing doctors or patients with a specific product. No, you’re compelled to join a company that will fix the healthcare system. Better yet, you should aspire to found(!) the enterprise that will somehow do this.

Grandiose company mission statements and PR messaging have become the butt of endless jokes, but the hits keep on coming.

Even the YMCA is getting in on the action, with billboards telling you that the gym made famous by the Village People now “Powers Your Purpose.” This likely only serves to cause anxiety in their intended audience given how many people spend their entire lives searching for it.  

We’re offered pseudo-profundity as a substitute for meaning (that thing we're told to find). Don’t know what to do? Come help change the world! Join us, do something big, and one day you too can be a Founder giving TED talks wearing jeans and Air Force Ones.

This Could Be You! - DALL-E

This kind of messaging is not completely misguided as meaningful work has been shown as a key component to a life well-lived. Ambitious people want this. The issue stems from a misunderstanding as to what it looks like in practice to actually find meaning in work.

It doesn’t need to be complex or grand in scale. You do not need to be a Master of the Universe. It does not need to have status – in fact this may even be a hindrance. You just need to do something that suits your innate abilities within some sort of commercial environment. Less searching, more doing.

I eventually took this simple, yet difficult, advice and moved into the field of executive recruiting. Doing something that aligns with my actual strengths instead of my perceived desires.

In something of a pleasant surprise, I found that I was actually very good at it. So much so that it led me to start a business in the space. Not because of some higher calling, but because I discovered a real market need through hours upon hours of intensive, focused, and productive work for clients who put their trust in me. Note: I have yet to give a TED talk.

This has also put me in a sort of ‘meta’ seat in which I have come to learn much about navigating careers through conversations with over a thousand business leaders from across dozens of industries. Things that seem so pivotal, like the space you operate in or the company you work for, are often much less important than you think.

These leaders, who come from all walks of life and rarely went to prestigious universities, share a set of commonalities in how they built their careers that any ambitious person can learn from:

1.)   Don’t think about it too hard. Find something you’re good at doing and then pursue it with vigor. Your primary goal in the early days is to create value. “Bigger” goals come later.

2.)   Something you’re good at typically means something you intrinsically enjoy doing. This means liking the actual work of a specific function within a business, not something you think you should like (a key distinction).

3.)   Be proactive and try to anticipate needs. Be it for a colleague, a customer, or a supplier – this is how you build deep relationships and have unforeseen ideas and opportunities come to you.

4.)   If you’re doing well and are offered a role in another part of the company you’re with, take it. This is how you “learn the business.”

5.)   Don’t try and plan out your whole career. Let it emerge as an outcome of the work you do and the value you create.

Take this approach and meaning will find you.

Or, put another way: “You can't connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future. You have to trust in something – your gut, destiny, life, karma, whatever. This approach has never let me down, and it has made all the difference in my life.” Steve Jobs said this, but what did he know?