In 2017 I graduated with my MBA in Finance and then went to work for a Fortune 50 company as a Senior Financial Analyst.

When I would tell people where I worked and what I was doing, many would be impressed. According to conventional wisdom, I had made it. I was working for a market leader with great benefits, awesome perks, flexibility, and a solid salary (I was making in the low 6-figure range).

So why leave those comforts to become the 3rd employee at an early stage healthcare software startup?

1. I wasn’t happy with my career trajectory

Look down the road 10 years from now if you continue on your current path. Do you like what you see? I didn’t.

We’ve all heard the phrase “if you like what you do you’ll never work a day for the rest of your life.” This did not apply to me. I didn’t hate my job, but there was almost nothing about my job that got me excited. I wasn’t very challenged, nor was I learning many new skills.

Most people think it’s a pipe dream to actually enjoy what you do, but I don’t agree.

You don’t have to just deal with a job they don’t like/hate to put food on the table and pay the bills. That is a limiting belief, and you shouldn’t fall for that crap.

Let me qualify my statement by saying, don’t go quit your job today (unless that actually makes sense for you), there is a time and a season for everything. Just make sure that you are critically thinking about how your choices today are putting you closer to your end-goal.

This job changes my career trajectory to be more in line with my long-term vision.

2. The opportunity

Had I stayed with my former employer, it would have taken me 7-10 years to get management experience. I’m not saying my final goal is to manage people, but it is my goal to grow in my career while I’m working for someone else, and that growth should come much quicker with a startup than with an established company.

There is also the outside chance that this company will grow and sell for millions of dollars, in which case, I’ll be rewarded. I’m not planning on that outcome, nor does it need to happen for this move to make sense. In fact, there could be very little company growth and my career change should still make sense, but the possibility is still there.

3. The ability to try new things

Have you ever wanted to try Operations, HR, Marketing, Engineering, Finance, Account Management, Sales? Well at a startup you can. So you can bet your bottom dollar that if I want to try out Marketing, I can easily create a path to make that happen.

It would be nearly impossible to do that in Corporate America. And who knows, I might be really good at Marketing, but without trying, I’ll never know.

As I add more scope and my role gets unmanageable and we’re in need of more employees, I can offload job responsibilities that I don’t like as much. As time goes on, I should be able to just keep job scope that I enjoy, which will make my job better and better.

4. The “fake it till you make it” factor

I have observed a major internal shift to become more entrepreneurial. I used to have the opinion that you’re either an entrepreneur, or you’re not, and I “wasn’t,” so I never pursued the path. I’ve changed my opinion and I think that you become what you think.

It’s easier today more than ever before to be an entrepreneur, heck, starting this blog was entrepreneurial! You don’t need to raise millions of dollars or hire loads of people to be an entrepreneur, you just need to act and capitalize on a market gap.

This is a step to further put me down the entrepreneurial path. Even though this isn’t my company, I will be creating processes, growing a team, selecting software solutions, influencing product features, and helping to determine the strategic direction of the company. All of these skills will be essential if I end up starting an entrepreneurial venture of my own someday, even if it’s just a 1-man internet operation.

5. This was the time to take a risk

My wife and I have been very smart with our money since we got married 5 years ago. We’ve grown our wealth quite a bit during that time, to the point that we could take off work for years and not even break a sweat.

We don’t have kids yet, so now is as good a time. This is another big perk of being smart with your money, it affords you to take risks when those risks make sense.

Don’t wait for “someday”


I had a co-worker at my former company who said it was a goal of his to make a similar jump to a small/mid-sized company “someday.”

I asked him why not take steps to make that happen today. The best time to find a job is when you don’t need a job, that way you can be super picky and only apply for your dream jobs.

Ultimately, he didn’t have a good reason, he’s comfortable where he is, and being comfortable is easy, but comfort doesn’t lead to exceptional results. If you want to live your dream life then sometimes you have to make tough decisions.

Hopefully, as you read this post something came to your mind that you know you’ve been meaning to do/change. Your path might not require you to join a startup, but I challenge you to act on whatever that thing is.

Are you– earning enough, saving enough, working in a field you enjoy, taking action on a passion-project, building a side-hustle?

What big changes have you made, or do you need to make, to accomplish your goals? Don’t wait for someday, start today.

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