What's Keeping You From Your Dream Job?

It’s been four years, but it feels like so much less. Tyler and I had gone out on our second date. I already knew he was different from the other boys, but I didn’t want him to think I was crazy, so I was trying to be casual – something I have never quite been able to master.

It had rained earlier in the night, so the road was glistening that perfect way it does when it’s just the right amount of damp for the reflections of the streetlights to have a twinkle effect. The twinkle effect always makes me think a little deeper.

He was driving me home, and as we turned into the driveway I asked him my favorite question to ask people. “What’s your dream job?”

“My dream job?” he repeated, as though it was a foreign concept.

“Yeah, your dream job. Like if you could do anything in the whole world for the rest of your life, what would you do?”

He didn’t answer.

I was just about to try and phrase the question a third way when he said, “Well…. I don’t know. I guess I’ve never thought about it.”

This blew my mind. 

I am tempted to misuse the word ‘literally’ here in order to emphasize just how mind-blown I was in this moment. 

This guy – this guy I was falling in love with had NEVER thought about what he wanted to do for the rest of his life. 

“So you’re going to just work? Like at any old job?” I was perplexed.

“Well, no, I want to have a job I enjoy.”

“Doing what?”

“I don’t know.”

Literally (I know, I know) mind-blown.

Now, here I am four years later, and this answer – the one where people shrug their shoulders and say they have no idea how they want to spend all the working hours of their one and only life – has almost become the standard when I ask this question. 

I’ve grown accustomed to hearing people say they don’t know what they want to do, but I have never really been able to accept it. There’s a tiny twinge inside of me that wants to help every one of those people figure out their callings. Their gifts and talents and dreams and desires and ideas and creativity. I want them to love what they do, because with everything in me, I believe it matters. It matters so much.

Since I quit my job and started running my media company full-time, this has become a common conversation I have with people. I run into old acquaintances or get emails or messages from friends saying “I’m so jealous you’re running your own business. I wish I could leave my job and go do something else.”

The thing is – they can. You can.


Now, let me pump the breaks and be loud and clear when I say I do NOT think everyone should start their own business. But I also don’t think you have to go out and start a company to love what you do. I know plenty of people who work for someone else and still totally love their career. I also know people who run their own business and hate it. 

This isn’t about who’s in charge; it’s about you knowing what you want to do and going out there and doing it. 

I asked people on my Instagram account if they were passionate about their career. I dug deeper with some of the ones who were not and found out why they stayed at a job they didn’t love. Here were their answers:

Financial stability

Fear of what others will think

Part of the process (working their way up the ladder)


Fear of failure

Worry that they still wouldn’t be happy at their next job

And the number one reason – they didn’t know what they would do if they left.

They didn’t have a dream job.

This is such a common occurrence. Somewhere along the way to adulthood, we wind up on these paths that lead us to different careers and we just kind of keep walking, never stopping to think if this is even what we want – what gives us life and excitement and purpose. 

This is not ok. 

We have to stop and think about what we want. 

What do you care about deeply? In what areas are you uniquely gifted? What ideas keep you awake at night? What market can you serve? What would it take to make you excited to get up and go to work every day? 

We have to ask these questions. If you’re fortunate enough to have found a career that you love and revel in and that is life-giving, I’m genuinely happy for you. Hold on to it, and remind yourself regularly why you love it.

But if you are mindlessly pursuing a mundane career you are not enthusiastic about just because this is where life brought you, it might be time to press pause and think about why you are there and what your goals are moving forward.

It feels good to do work that matters. You should not dread going into the office every day. Your dream job is going to look different from mine, but I hope you know what it is, and I hope you are whole-heartedly chasing after it.

At the end of the day, your job is not who you are – it’s just what you do. So don’t beat yourself up too much if you feel like you’re in a sucky position right now. It doesn’t define you. You are enough exactly as you are. But that doesn’t mean you don’t deserve to love the work that you do. 

So figure out what you want to do, and go do it. Because the world needs more people doing what they love.

Are you pursuing your dream job? If not, do you know what it is? Tell me in the comments!