Hailey Heishman

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How I Quit My 9-5

One year ago I was sitting in an office bombarded by emails, attending never-on-time meetings, and wondering how I could replace my income to quit my job. This was the burning desire that I was afraid to vocalize because I loved my job. It was everything I ever hoped for and worked for — but something was off.

In college, I decided my major would be Communications and Advertising. It sounded fun, professional, and respectable so I decided that was what my life was going to be.

Only I didn't even consider what life would be like after college. I certainly didn't know the “All-American Dream” was not my dream at all. No one had filled me in on the reality of “being an adult” and the fact that it’s not all smooth sailing and happily ever after from there on out. Maybe I was a bit delusional back them ;)

This confused me because I did all of the things I was supposed to do. I checked all of the boxes as I continued to work my way toward my “dream job” (and life). These were the things that would make me someone in the world.

It wasn’t until I was two months into my 200-hour yoga teacher training in 2016 that I finally looked my life in the face and saw that I wasn't doing what I love. I wasn’t giving back to the world in a meaningful way and something had to change soon.

So, I began asking myself...

"Why am I so unhappy...so unfulfilled?”

"Why am I so tired after all the work and time I put in?”

“Why isn't this what it was supposed to be?”

“What do I need to feel...good?”

I had to throw all of my expectations out the window because I wasn't living my true purpose and I knew it.

First I had to figure out how to leave financially. I couldn't just walk out tomorrow without a tentative plan for how I would earn money. That wasn’t an option. I needed to take time to write it all out on paper to actually see that it could be real.

I sat down on my living room floor with papers and notes scattered everywhere and started doing the hypothetical math of how I could replace my income:

- Teach X amount of yoga classes per week

- Create online products and sell so many a month

- Write my book... and get a book deal

- Land a few freelance marketing clients for stability

I thought, “This is doable. A little ambitious...but definitely doable.”

Then, I pulled up my bank account to see what I was actually making on a monthly basis. I calculated the hypotheticals and the total number equaled exactly what I was making from my salary. No joke.

I sat on my living room floor crying because I just couldn’t believe how real it was. There it is. Income replaced. It won’t be easy, but it’s absolutely possible.

I’ve learned that there’s a huge difference in knowing and acting. We can know something for a long time, but I believe it takes a whole other part of you to actually start acting on that knowledge. It’s kind of like knowing you should move your body or eat whole, real foods and then actually making the choices every day that bring that knowing to life.

Our daily choices shape our lives just as much (or more) than our daily thoughts.

Between the knowing and acting I would ask myself,

What if this doesn’t work… how could I ever go back when I know what I know?

Can I “throw it all away”?

Does leaving mean it’s gone?

Does “quitting” mean I’m a failure?

No. That can’t be true.

I decided I’d tell my boss at the end of summer and finish out the year to get all of my work organized. Well...naturally plans like these are never really in our control. The conversation got bumped up to July and I let it all out. Knowing good and well my boss would probably tell me, “Great, this is your two weeks”. But, he didn't. Instead, he asked, “What do you need to be happy? What do you want to do next?”

Uh. What? I think I was in shock for the next few days trying to decide what was best for me. Turns out I’m the only one who knows that...and I had to decide.

The best way I’ve found for getting answers to my questions is by grabbing my journal and writing the question that I have, over and over. I write the question until finally, I start writing answers. I let my freewriting do the work.

I believe we have the answers to all of our questions inside of us somewhere. The problem is we rarely ask ourselves. Instead, we outsource, to friends and family and strangers, begging for the answers to our problems when only we know the true answer.  

I gave my notice to leave and immediately felt lighter. I cried and smiled and cried some more.

On Day One of “being my own boss”, I got a phone call from a friend sending business my way. My first real client on my own. Opportunities were opening up around every corner and it was honestly kind of surreal.

But it wasn’t luck. It was the result of all the work I’d done at the agency. Everything I left did mean something. The time I spent there was time spent building up my reputation in my field of expertise and creating connections that would fuel this next chapter. Turns out, I didn’t “throw it all away” — I simply took the next best step I needed in my life to thrive and my choices got me here.

Leaving doesn’t mean I’m a failure. Leaving doesn’t mean people will hate me or be disappointed in me. Leaving isn’t the end of the world — it’s the beginning.

The truth is, it is possible to create and build whatever you dream of daily. I discovered that I can be the fullest Me I could ever imagine, but I couldn’t stay and have that too.

Something my partner says is, “In what conditions would you thrive?”

I ask myself this question a lot. Mostly because of the beautiful nature of this always-evolving life. I’ve come to see that my happily ever after lies in the here and now. Keeping a fresh perspective on the life in which I would thrive helps me adapt, grow, and continue to learn every day.

I knew I needed freedom from daily tasks and work-place politics. I needed to be in control of my own schedule so that my creativity could flow. I needed space and time to create. And, I wasn’t getting that where I was.

Consider asking yourself this question and see what comes up.

“In what conditions would I thrive?”

Jumping wasn’t easy. It’s actually the hardest thing I’ve ever done. There were days where I cried and questioned if this was going to work out. There were days where more doubt ran through my mind than ideas. Getting here was exhausting and an emotional roller coaster, but being here is the most incredible, “dream world come to life” I could ever imagine.

I don’t believe everyone should quit their job and “jump”, but we likely won’t get our dream life handed to us on a silver platter. I believe we have to do the work necessary to discover what’s true for us. The work that involves asking the hard questions, trusting our gut, and having a little faith.

You know the answers to your questions, so start asking.


-H