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Writer's pictureAmanda DeBernardi

Surprising Lessons Learned After One Week of Full-Time Entrepreneurship

Updated: Apr 3, 2023

The Great Resignation is not for the faint of heart

Last week, I traded in a job that offered a paycheck via direct deposit at regularly timed intervals for the rollercoaster of self-employment.

Now, my job is to sell myself, my ideas, and my energy. Nothing has poked at my deepest insecurities like entrepreneurship.

It has even uncovered some fun new ones:

  • Issues with self-worth and confidence? ✅

  • Crippling anxiety about charging for my services? ✅

  • Worried about not being cool enough for social media? ✅

  • Playing out the mental drama of spending a million hours making something with my heart and soul only to hear crickets when I launch the sales page? ✅✅

So why did I leave my job?

Because I am ready to live my life according to what is actually important to me. I crave space and simplicity.


I finally acknowledged that there are parts of myself that I have locked away because I was afraid of their need for freedom. I realized that I was in a cage but the door was never locked and I could leave at any time.

Stepping out of the cage feels uncertain and vulnerable. I am not sure what is out there, but so far nothing has ambushed me.

Here is what I know after one week:

I am tempted to create another job for myself

Old habits die hard. Total freedom over my time and energy feels unsafe because I am used to structuring my day in a way that molds to institutional norms.

What does one do if they do not show up to a prescribed place at 8:00 am and turn on their computer, check their email, and prepare to die slowly in a windowless cell?

My husband came home for lunch and I felt a compulsion to report to him everything that I had done that morning. I listed the completed tasks that I assigned myself. His response was a confused “Good job…?”

It is a strange feeling to not have anyone holding you accountable for productivity. Learning to validate my own progress instead of relying on someone else to let me know that I am worthy and valuable is a skill that I am still refining.

What do I do with the afternoon if I am not counting down the hours until I can go home? One of the first programmed habits that I am focusing on deconstructing is the idea that I have to get everything done during a certain set of hours.

I can grocery shop in the middle of the day but it feels weird

I am getting used to options.

I went to the grocery store at 2:00 pm and I had an underlying feeling that I was going to get busted doing personal errands during work time.

Then I remembered that I am in charge of myself.

I took the time to appreciate the evolution of my shopping experience. How nice to be able to be at the store when it was less crowded. I didn’t have to rush or be vigilant for co-workers who might tell on me.

I used to occasionally sneak away during the day to pick up a prescription or some pretzels and Capri Suns because it was my turn to provide the little league team snacks. Even though the thrill of being bad for running errands on work time is gone, it feels really good to let my life flow instead of trying to squeeze everything into my calendar.

The highs are really high and the lows are really low

Staying in the present moment is challenging when you are going through dramatic change.

Time autonomy was my main motivation for leaving my job. When I was fantasizing about all of the freedom I would have as a full-time entrepreneur, I didn’t count on the stress I would feel from the absence of obligation.

I am used to some arbitrary point in the future dictating the present. Pressure is my default. Pressure to succeed at work, climb the ladder, and earn the recognition and approval of others was a main source of motivation.

What now?

There are times when I can pause and feel the unbridled freedom of entrepreneurship. It feels really good and if the moment hits me just right, I smile and maybe even dance a little jig.

Equally prevalent are the moments of sheer panic, where the reality of ultimate personal accountability completely overtakes the joy of freedom. I realize that I have no one to blame if this all goes south. That is its own kind of freedom, but this kind lands more like a cement block on my chest.

How do I decide what I want and how to proceed if there is no one to please but me? I am willing to fuck around and find out. So far, I have no regrets over my decision to join the pantheon of 9 to 5 ex-pats that make up The Great Resignation.

This has been a two-year plan and it seems a little surreal that I was finally able to gather enough gumption to quit my job. I knew it would be challenging, but the intensity of this emotional roller coaster has caught me a little by surprise.

All things considered, I wouldn’t have it any other way.


 

Wanna stay in touch? I send out an email newsletter with journal prompts and reflection questions at each new moon and full moon. Plus, I will give you my Self-Care Menu PDF as a little bonus.


If you want to support my work and my coffee habit, you can do so here. ✌️



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