9 Crucial Questions – How to Find a Job You Love.

Updated August 8, 2021

I was having a conversation on reddit the other day. Someone asked how to find a job you love.

So I answered, and someone else said to me, “You know not everybody gets to find their dream job. Some people just work jobs they hate because they make a lot of money and they do the thing they love on the side.”

And that’s one-hundred percent, unequivocally true!

I would say that MOST people are probably doing jobs they don’t love and then on the weekend they’re going and trying to figure out where their passion comes from.

But today I want to ask:

  • How could you actually get there?
  • What if you wanted to be one of those people who does what they love?
  • How can you find a job you love?

There’s a guy in my hometown who makes coffee. He roasts his own beans. He drives to another city to get the best beans imported.

He actually loves what he does.

When you come in for a cup of coffee, the passion that he has for every single cup that he makes literally spills over—haha, see what I did there?—and you can taste it in the product.

So the question is, why can’t you be like that? What would it take to figure out what you love to do and do it for a career?

Here are 9 questions to ask yourself if you want to know how to find a job you love. And–spoiler alert–it’s not only about finding jobs. It’s putting the job within a wider discussion of the life you want to live and what needs to be true for you to be living it.

If you’d rather watch this post than read it, here ya go! If you like text, keep scrolling!

1. What do you believe to be true about the world?

This seems abstract, but I want to start here. What do you believe to be true about the world?

There’s something that I learned from studying religion. Everyone’s idea of what is meaningful and what purpose should be is wound up into a whole bunch of beliefs and expectations that we have about the world–our worldview.

Religions are the obvious example of this. They give their followers a way to think through meaning. People who belong to a religion can conceptualize their identity in this box that kind of makes sense to them.

A religion usually gives you an idea of the things in life that are worth chasing. It tells you what the end of your life should look like, or gives you an idea of how to treat other people.

Even in a society where we are more and more secular, there are still beliefs that dictate how we build purpose.

This might be a political affiliation.

Maybe you love capitalism or maybe you hate it.

Maybe you think social welfare is the answer or maybe you think it’s a problem.

Some people love their hometowns, and can’t imagine living anywhere else. They want their town to prosper and the people in it to be healthy and happy.

Name these beliefs you have about the world when you’re trying to find your purpose and live within them. If you hate capitalism, don’t go work for a hedge fund. If you love it, be careful about working for a non-profit.

Your beliefs will dictate where you actually find meaning and how you should devote your time to chasing that meaning.

Figure out what it is that you think is true about the world, because your purpose and the work that you do and the job that you eventually get should somehow fit within that.

Your beliefs will dictate where you actually find meaning and how you should devote your time to chasing that meaning.

2. What is the biggest problem that you would solve in the world if you could?

Everybody has a different answer for this. Some people want there to be a cure for cancer. Some people want to combat ignorance. Some want to see violence eradicated.

Some people have more local goals. Some want their local businesses to have ways to tell their stories online. Some want to have local, organic vegetables.

If we’re going to fit into work that feels like it has purpose, I really believe we should be working to solve problems that matter to us.

I started Roostervane because I really hate that students are graduating and don’t actually have any idea how to get a job or how to do something that they love with their degree.

So that became the problem that I devoted my attention and my effort to solving.

If you want to do work that is meaningful ask yourself what problem would you like to actually solve. If you could be a part of a solution to a problem, whether it’s a huge problem like world peace or whether it’s a small local problem like a supply chain issue, what would it be?

If there’s something that really bugs you, this can be a really good place to start. A lot of businesses are launched because of this.  

3. What do you get so engrossed in that you forget to pee?

Have you ever had those moments where you get completely into a zone? Experts call this “flow,” when you disappear into a project or your work and time seems to stand still.

When you do this, work is rhythm. It’s music. It’s the furthest thing from monotony.

It feels good, and we don’t want to stop. Even to pee.

I felt this recently making an intro video for the Roostervane YouTube.

I’m really creative, and when I write an article or edit a photo time stands still. And I’m realizing it’s the same thing with video.

I made a new intro video in Adobe Aftereffects. It took me like 6 hours. And I didn’t get up, even to pee.

I got so into flow I couldn’t stop doing it. I was so in the zone and I didn’t want to get up.

I didn’t want to stop. Normally I go to bed at 9:30 or 10:00—because I’m a really old man and I have small kids who get up in the morning. But this time I went to bed at 1:00am.

What is it for you that gives you that flow? What is the thing that gets you so engrossed in what you’re doing that you forget to pee?

I don’t know who first asked that question but it’s a good question to ask.

What is it that you get so deep into that that you can’t get out of it? That’s a really good place to start when you’re thinking about finding a job that you want to do.

Mihaly Csikszentmihalyi’s Ted talk about flow.

4. What’s an area you want to keep growing in? Like, you seriously want to keep getting better and better?

There is probably already an area that you have flow in, but then the next question is, “What’s an area that you want to grow in?”

For me it’s business. I love business. I’m really trying to learn all the time how to get better at it, and there are a lot of different parts to that, but it’s something I can never learn enough about.

There’s something like that for you too, whether it’s learning to manage a project or make the best croissant.

We are fulfilled when we grow, so this should be an area we consciously identify our purpose in.

We feel this sense of fulfillment at pushing our own limits in terms of what we’re capable of and becoming a better version of ourselves.

Oprah Winfrey has a saying that I love:

“No matter what challenges or setbacks or disappointments you may encounter along the way, you will find true success and happiness if you have only one goal — there really is only one, and that is this: To fulfill the highest, most truthful expression of yourself as a human being.”

Oprah Winfrey, Harvard Commencement Speech, 2013

That’s the question to ask yourself. Where do you want to grow? What’s it going to take to bring you to that highest, most truthful expression of yourself?

5. What is that thing that you would go learn if you could, if money wasn’t an object?

I believe that learning is not limited to university. Learning is life! And constant learning and growth is the best way to live a life that has meaning and purpose.

When you pick a job, don’t pick something that you can do 100% of. Shoot for something that you’re 40-60% competent in. (I know, I know, someone needs to hire you first. I get it.) This way, you can get paid to learn! It’s one of the most rewarding experiences ever.

6. What would you spend your day doing if you won the lottery?

I grew up in a town of people who were obsessed with winning the lottery. They were mostly blue-collar people.

And they talked about it all the time.

“When I win the lottery, I’m going to open a wood-carving studio.”

“I’m gonna retire to Florida.”

“I’m gonna golf all day.”

“I’m gonna open the best burger joint.”

“I’m gonna start an outfitter business to teach people how to fish.”

I don’t know about Florida or golf, but some of those things are actually jobs!

People dreamed about living the lottery so that they could work someone else’s job! That’s bizarre!

If you have a dream that relies on winning the lottery, a much better question to ask is, “How could I achieve that thing without actually winning the lottery?”

Whether the answer is that you want to flip furniture or do graphic design or learn online marketing or play the stock market, figure out how to make your lottery life your real life. Believe it or not, there’s a much better chance that you can give yourself your dream life than that the lottery will. And, by the way, you’ve got a better chance of becoming a millionaire with your own work than by winning the lottery.

An estimated 3% of American households have 1 million dollars in net worth. By that, we might argue that you have a 1 in 33 chance of becoming a millionaire at your own hands. You have a 1 in 14,000,000 chance of winning the lottery.

I like my chances of doing it myself better 😊

7. What would you try to create in this world if you knew that money didn’t matter and you couldn’t fail?

Okay let’s stick with the theme of, “if money didn’t matter.” But also, “What would you try to create if you know you couldn’t fail?”

Our fear of failure holds us back from a lot of things, and building something that we truly believe needs to be in the world is definitely up there.

You have an amazing dream. Something that the world needs.

And you think to yourself:

  • But it’s probably not going to work.
  • I’m not good enough.
  • What would people think?
  • What if I failed, would people laugh at me?

This type of thinking stops the greatest achievements of humankind. There are tremendous advances to our species that have never happened because of this type of thinking.

So if you have something to give the world, use this “fear of failure” question to figure out what the heck it is.

Then, figure out how to build it anyway! Everyone who does great things is afraid. The only question is whether you’re going to grow past your fear or let it define you.

8. What kind of lifestyle is an absolute must for me?

My life requires time spent in the outdoors. I love to be outside. It makes me happy. It rejuvenates my spirit.

Some people get energy from cities. Some of my friends who live in Toronto or New York feel at home in a big city the way I’ll never understand.

So, for me, trying to build a career as a hedge fund manager on Wall Street wouldn’t actually fit my ideal life.

Figure out what your non-negotiables are in terms of the lifestyle you need to be happy.

If you want to retire to a yacht in the Mediterranean, you might need to do the hedge fund. If you want a simple life in a tiny house in the woods, you might come into town twice a week to work a shift at Starbucks.

Whatever life you desire is true for you, and it’s important to honor it when choosing a career.

I always imagined working from home, getting paid to do stuff online but also helping people. I thought about it as I rode a smelly commuter bus into the city—literally commuting 3 hours some days.

This isn’t my life.

So I thought about what I needed. I wanted to create something to help people that could ideally also bring in some revenue. I wanted something that was accessible online. I wanted access to the outdoors.

And, I wanted to build a company to help students launch amazing careers. I was so angry that people were doing degrees that were leading nowhere.

Everything came together with Roostervane.

9. What’s the best way to get to my vision?

So when you answer the 8 questions before this and figure out what is true for you and your world, what do you need to bring that life into existence?

  • Do you need a certain job to do it?
  • Do you need to create your own job, even if it’s something that doesn’t exist yet?
  • Do you need to build a network that includes certain people?
  • Do you need to go back to school?
  • Do you need to take a sales job to learn to sell?

You can start to create your own roadmap for getting where you want to be.

Maybe you want to open a bakery, and you need to learn to bake. Maybe you want to be a YouTube star and you need to learn to edit videos 😊


These are nine questions you can ask yourself if you want to know how find a job you love! Try them and let me know what you think! If you like the results, you can email me at chris@roostervane.com and tell me what dream you’ve decided to follow.

And you can watch the video I made about this post! I’m excited to see where it takes you.

Read More:

if you liked personal brand tips, you might like this video on vision



Weekly articles, tips, and career advice