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Should You Quit Your Job and Start a Business?

Eddie Yun Shieh
Dec 10, 2018 · 5 min read

Should you leave the security blanket of a steady paycheck in favor of a life of passion and pursuit of wealth? Should you stop building someone else’s legacy and start building your own? Should you stop letting other people decide what you’re worth and start seeing what you’re really made of?

My friend, I know exactly what you’re going through.

I used to think myself in circles like this:

Ugh! I hate my job. I’m going to go be a freelancer. That way I can choose the projects I work on and get to work whatever hours I want, wherever I want. Ted says he only works 6 months out of the year because he charges double what I’m getting paid now. Chloe says she gets to travel whenever she wants because she can work from anywhere with internet. Hmm, I’ll probably have to take some small projects at first, which means juggling multiple clients. I hear that’s really hard because you lose productivity by task-switching like that. Maybe I should try to get a 6–12 month contract somewhere at like Google or Netflix, so I don’t have to keep finding new clients. But those contracts generally require that you’re on site, so it’ll feel just like being an employee again. Plus whatever I get paid by the hour, I’ll have to take off 30% for taxes, plus pay for my own insurance, which…who knows how much that is. And freelancers usually get assigned grunt work that no one else wants to do, so I won’t have any creative liberty. Having clients is basically just like having multiple bosses all telling me what to do. At least right now I only have one. UGH! Forget it!

Most people think of it as a question of security vs. freedom or fulfillment. They think they’re choosing between “having a boss” or “being your own boss”. They think it’s an accounting challenge or a product-market fit challenge. But it is none of those things.

It’s about something much more fundamental and transformative. It’s about who you want to become.

To find the answer for yourself, the two questions you should be asking yourself are:

  1. How am I being asked to grow?
  2. How do I most need to grow?

Here’s the thing, any path you choose will involve struggle. Whether the struggle is in striking out on your own to build a business or in reconciling your current job situation, you will be grappling with yourself to make shit work. So which struggle would you like to embark upon?

The one you choose will determine how you grow and who you become.

In 2015 I decided to leave my job without anything lined up. I felt that I had reached a breaking point. I felt so volatile and resentful that sometimes it took all of my willpower to keep me from storming out of meetings or screaming. I had trouble focusing because I was constantly daydreaming about the “other life” I could be living. I couldn’t bear to be in my reality. I felt like a liability to the company and to myself.

I was being asked to grow. Not by any person, but by my situation.

I could have lied. I could have told my boss I wanted to quit because I wanted to work in a different company that offered the exact opportunities he could not. I could have told him that I wanted to pursue my “true passion” somewhere else, or go back to school. I could have come up with answers to every objection and made a smooth exit that made sense in the retelling. Or I could’ve just left.

That would have been easier than what I did, but I wouldn’t have grown.

What I did was let my boss see me. I let him see my sadness, anger and fear. I let him see that I had no idea what I wanted or who I was, and how it was killing me. I told him I needed space to find myself which is why I was deciding to leave. I told him I knew these reasons made no practical sense and weren’t very smart. And that I would not convince him of their validity because I couldn’t. I didn’t need him to understand. I just needed him to hear me.

It was awkward. It was scary. But it was worth it. Listening to my intuition, asserting my needs, and speaking my truth were exactly ways I needed to grow. My journey began with that conversation.

Nowadays, my business feels like a natural part of the journey. I design my life around trusting my intuition and living authentically because I keep growing in ways I want to that also help me be a better entrepreneur. When I’m being my best self, I’m productive, confident, clear-headed, decisive, courageous, and creative. Qualities that I need to be successful.

The return I get from investing in myself in this way makes a strong case for continuing down this path of being a solopreneur.

But let’s rewind. What if I had stayed? How might I have grown then?

Let’s say I had decided to recommit to and grow at the company.

Instead of daydreaming, I learn to stay rooted in my reality and sit with my discomfort. I learn to manage my anger and resentment and reframe those emotions as fuel for a worthy challenge. I learn to stop blaming others for my circumstances and take responsibility for myself. I learn to be strategic in asking for help and making requests to change my situation. I learn how to build a case for what I want and take the lead in implementing it. I learn how to nurture relationships and identify advocates and mentors. I learn how to impact an organization from the bottom up and create a better life for myself along the way.

This would have yielded tons of growth and transformation, too. But a very different kind. I would be a very different person today if I had chosen that path.

Is it better or worse? Right or wrong? I dunno. It just wasn’t the path I chose. And now I’m just focused on living my best life while making adjustments as needed when they arise.

You see, it’s not about making the right decision, it’s about making the decision right.

And when in doubt, take a long, honest look at yourself and choose the direction you most need to grow. Then fully commit to that journey. You won’t regret it.

Originally published at

Eddie Yun Shieh

Written by

I help minorities in Tech design fulfilling lives, so they can enjoy the success they worked so hard to achieve.

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