If You Can’t Find a Job You Love, Ask Yourself These Questions

The Biggest Test

Here’s what Felix Dennis writes about finding a job you love in his book How to Get Rich:

“[Choosing your career is] the biggest decision over which any of us is likely to exercise real control. We do not choose our parents. We do not choose our nationality. We do not choose who we fall in love with. We do not even choose the personality or character of the children we bring into the world or our own personal characteristics—random configurations of DNA do it for us. But we do get to choose, if we are determined enough, what it is we want to do for a living. Most of us flunk this test.“

Felix Dennis, How to Get Rich

Since you’re reading this post, I imagine you’re among the “most of us” who are flunking this career choice test.

There’s no shame in that. It’s a doozy of a test. Not only does it have a million options to choose from, but there’s also a blank “Other” space at the bottom. And cheating off of others won’t help you. Worse still, our evolutionary wiring sucks us toward comfortable mediocrity rather than fulfilling work.

But you can approach this challenge systematically. Over nearly a decade of studying career fulfillment, testing frameworks, and helping others find their path, I’ve developed a framework that works. It helped me discover a dream job I never even knew to dream of. More importantly, it’s helped countless others break free from societal molds to craft truly energizing careers.

This framework has four essential parts:

1. 💨 The Fuel – What drives you forward
2. 💪 The Reward – What keeps you going
3. ⛵️ The Craft – How to make real progress
4. 🌊 The Adventure – How to enjoy the journey

Each section contains specific questions designed to help you systematically narrow down your options and find work that genuinely energizes you and the people you impact. They’re not easy questions, but they’re more manageable than the overwhelming “How do I find a job I love?”

Part 1: The Fuel

What’s your problem?

Should you “follow your passion”?

Or should you develop expertise until professional passion emerges?

Career-choice-ologists make their own careers from debating and defending their answers, but I believe the better first step of your job search process is to look for the opposite of what you’re passionate about:

What problem in the world makes you angrier than most? Something that others shrug off but keeps you up at night? Something that hits you in the gut when you see it happening?

That problem is your fuel. It’s the headwind that can fill your sails – if you let it.

Here’s my problem.

I can’t stand our innate tendency to stick to, settle for, and even defend the status quo. When I see someone trapped in societal molds or settling for mediocrity because “that’s just how things are done,” it lights a fire in me.

Take the Star Wars Kid in this video, for example:

I chuckle with everyone else at his dorkiness. But I smile even harder because I feel inordinately happy for him for having found something weird he’s so into.

And I feel equally inordinate disdain for people who mock him. I want this kid to assemble an army of “nerds” like him and vanquish those bullies. Better yet, maybe he can show them how to stop caring what other people think and start doing their own thing, too.

Crazy as you may think that sounds, just writing that gave me goosebumps. And that motivates me to keep plugging away at The Zag—and keep loving it even when it’s a struggle and people make fun of me for it.

Pick a fight you can’t win.

Like any actual fight the Star Wars Kid might get into, I’ll never win in my battle against status quo bias. All I can do is inflict a little bit of damage.

And that’s a good thing. That means that I’ll always have a steady source of fuel for the little flame under my butt.

Make sure whatever problem you take is equally unbeatable, and not a goal. As we’ll see shortly, it’s more like a constant headwind you can use to fill your sails.

Other people’s problems.

To help you find your problem, here are more examples of others’ and what they’re doing about it:

• Hairdresser: For one of the hairdressers in this article, the problem she’s taking on is people’s struggle to express themselves. In her job, she has to read between the lines to understand her clients’ desires and use her expertise to make sure their hair reflects that.
• Software designer: In his excellent talk, Bret Victor shares his problem: ideas that are stunted or stillborn because people can’t get immediate feedback on what they’re doing. So he works in designing products that rescue those ideas from dying.
• Small business owner: My brother’s problem is that technology is causing people to physically drift apart and into their own little bubbles. He’s doing his part to fight it and bring people back together again by owning businesses like a cafe and a climbing gym.

Find your problem and you’ll find your fuel. It’s not about passion or expertise – it’s about what consistently energizes you.

Part 2: The Reward

What’s in it for you?

The problem you take on has to serve some greater good. But if that’s your only motivation, you’ll burn out. To find the job you love, be honest with yourself about your selfish motivations.

Quit faking like you’re a saint and ask yourself:

Stop pretending you’re so selfless.

These days, everyone claims noble motivations:

• Doctors and nurses do what they do to “save lives.”
• Soldiers are “fighting for freedom.”
• Engineers are “building the future.”
• Entrepreneurs are “solving the world’s problems.”
• Stay-at-home parents are “sacrificing for their kids.”
• I’m “inspiring people to get out of ruts to make the most of their lives.”

We’re all heroes.

Yay.

There’s nothing wrong with professing such altruistic motivations. But it is wrong to delude yourself into believing it’s the only reason for having chosen your career. When you forget what’s in it for you, work becomes a draining act of martyrdom rather than an energizing pursuit.

Dig into your ego.

Look for the internal, ego-feeding rewards that light you up. Don’t focus on surface-level rewards like money or power – those are just means to deeper ends. Instead, ask yourself:

• What’s your answer to, “I want people to respect me for _____”?
• What do you want to be able to shove in the faces of your haters?
• Decades from now, when your future self looks back on what you’ve done, what do you want them to be most proud of?
• What measure are you using to keep score in the game of life?

In my case, by fighting status quo bias I want to prove to the world (and my future self) that my ideas are worth listening to. And I want people to come to me for creative solutions, rather than think, “Who is this bozo blogger shouting to nobody on the internet.”

Part 3: The Craft

How can you make the most possible progress?

If the problem you’re taking on is an incessant headwind and your reward is the ego-boosting respect you get from making progress, your job is what allows you to build a ship to sail right into it.

This draws on Maslow’s hierarchy of needs. You’ve probably seen the old five-tiered pyramid before. Well, that’s been replaced. The new-and-improved model’s a two-part sailboat:

Let’s look at how to apply this model to make better career choices that:

1. Protect you from sinking, and
2. Help you fill your sails and make waves.

1) Protect yourself from sinking.

If you’re early in your career or in a rough patch in life, worry less about landing the perfect job and more about finding something that protects you from sinking.

These are the so-called “security needs.” They include:

• Safety: A sense of stability and protection—financial, physical, and otherwise—against life’s unpredictability.
• Connection: A sense of belonging and supportive network.
• Self-Esteem: Finding self-worth, mastery, and a growth mindset.

But just because you’re reinforcing your security needs doesn’t mean you can drift around and lose track of your problem. Find meaning in any work by remembering to ask yourself:

A. Identify and hone your talents.

“You can’t know if you’re talented at riding hippos until you try,” write the authors of Dark Horse: Achieving Success Through the Pursuit of Fulfillment.

Do, experience, study, and work on different things in search of what comes easier to you than most. This can take years, even decades, to find. But once you’ve assembled enough clues, you can use tools like AI to find your (not-so-)superpower, like I did.

B. Keep your eyes on the prize.

Stay motivated by remembering that the more secure a hull you build, the better equipped you’ll be to seize opportunities in the future. Even in a job flipping burgers, you can save, expand your network, and work on yourself.

C. Find meaning in the mundane.

Look for ways to make meaningful progress against your problem, no matter how trivial or boring your role may seem.

For example, a hospital custodian named Luke from this article found ways to meaningfully combat his problem, unnecessary suffering, by reframing his role as being responsible for making the hospital more comfortable for everyone inside it.

Or when I was working as a corporate accountant, I found ways to challenge the status quo by redesigning company reporting processes.

By finding meaning in the mundane, there’s a chance that you may even be able to turn a job you hate into a job you love.

2) Fill your sails and make waves.

When you have a secure hull, an idea of where you want to go, and wind in your face, find a job that fills your sails by asking:

Here are some questions worth considering when assessing your options:

• What jobs can increase the size of your sail? You increase the size of your sail by improving your skills. Writing (and now making videos) is a hard skill I can keep getting feedback on and improving at by blogging.
• What’s a drag for you, and what jobs minimize it? You reduce drag by not doing work you hate to do. For example, I don’t like managing people, fixed schedules, or dealing with colleagues and bosses, so being able to work for myself on this blog is a blessing.
• Does it have to be working for yourself? Autonomy is important and being an entrepreneur is the cool thing to do these days, but keep in mind that working as part of a bigger business may give you access to resources that allow you to move faster.
• Who’s taking on a problem similar to yours and kicking butt? Look for role models and mentors. How are they doing it and how can you possibly do something similar?

If you have security and have come up with clear answers to the previous questions we looked at—What’s your problem? and What’s in it for you?—you should be able to come up with plenty of job ideas.

Best of all, they’re all good ones. You can love any job that meets your criteria.

For example, I love working on The Zag but I could also see myself loving a potential career analyzing big data to help people find products or other people that match their inherent interests, or working on a huge status-quo squashing project like autonomous driving and redesigning cities.

Part 4: The Adventure

What job makes for a great journey?

On the scale of human history, nothing you or I do is going to make a lick of a difference. We’re going to die and that’s the end of our story. And the problems we attempted to take on will continue blowing in people’s faces.

But we gotta do something to pass the time, right?

And, in that case, we might as well make our trips down our career paths a bit more adventurous.

Do it for the fun of it.

Whatever job you do, don’t do it for the results. Do it for its own sake—because fighting against your problem fulfills you, even if you can’t win. That’s the only way you can be sure life never gets boring.

Here are a couple extra questions that might help you figure out what kind of meaningful but meaningless adventure to go on:

If you could pick any job, but you’d have to work at it 40 hours a week for the rest of your life for a fixed salary of $100,000 a year, what would you choose?

I like this question for two reasons. First, it takes away financial incentives that sway decisions the wrong way. Second, because it’s permanent it forces you to think of a worthy destination-free journey.

What would you do even if you know you would fail?

I got this question from Seth Godin on the Tim Ferriss podcast. Think about the skills, experiences, and connections a job could give you even if that job doesn’t work out.

Don’t choose a path. Choose a direction.

Winds change. People do, too (even you). And shit happens. So don’t waste your time trying to predict it. And definitely don’t set yourself on any career path you can’t veer off of.

Set a general direction and be open to improvising. When unanticipated paths open up, be prepared to take them. And when unexpected obstacles block your path, shout out “Plot twist!” and find another way.

Ten years ago, I would have thought I’d be the CEO and founder of some disruptive start-up by now. But here I am blogging. The lame but useful truth is the only thing I’m CEO of is my life.

Another ten years from now, who the heck knows?

Maybe I’ll still be writing on The Zag. Or maybe my LinkedIn resume will have a new job atop it. I don’t know. All I know is this:

As long as I’m still making progress against my problem and getting the ego-boosting rewards I need, I’ll love my job.

Your Final Cheat Sheet

To recap, here are the questions that can help you narrow down your career choices and improve your chances of finding a job you love:

• What problem pisses you off more than most?
• What job positions you best to harness that power?
• What’s the ego-stroking reason do you want to succeed?
• How can you make progress, regardless of where you’re at in life?
• What work guarantees you a wild ride, no matter what?

These aren’t easy questions, but they’re more manageable than, How do I find a job I love?

And if you manage to assemble the answers, you might be as lucky as me to come up with a craft that allows you to take your life on a rewarding adventure.

More Fresh Perspectives on Finding Your Calling

If conventional approaches aren’t working for you, my unconventional suggestions can’t be any worse: