What I Learned When I Let Go of a Regular Paycheck


Many of the people I work with yearn to be their own boss, but balk at the uncertainty that goes with it. For the past two years, I’ve been flip-flopping (sometimes daily!) about whether to hang on to my very-part-time-but-regular-paycheck job.

While I didn’t have that many hours at this company, therefore, not a big paycheck, they did deposit money into my bank account every two weeks. Reliably. Plus, I didn’t have to do any marketing and I loved the clients.

The struggle has always been around how much of a distraction it is from pursuing my private coaching practice. The administrative side of things was much more cumbersome than with my own practice; I was driving to meet people, often for just a single appointment so it wasn’t an efficient way to earn money.

But…it was something regular. I was reluctant to leave, unsure how I would make up the income, however paltry it might have been. I’ve felt really stuck about this decision for a long time, and always go back-and-forth about what the “right” thing to do is.

Here are all the reasons I told myself for staying:

  • I like the clients.

  • They’ve offered additional training.

  • I don’t have to go find clients; they just come to me.

  • It’s good for me to get out of the house.

  • It might not be a big paycheck, but it is a regular one.

At the start of the new year, I decided to leave. And that’s when I learned what I’d really been holding on to.

I left because I wanted to have more time to focus on my own coaching business, or so I said. Yet, last week here’s what I did with all that extra time.

I procrastinated. Did laundry. Walked the dog. Repeatedly checked the email account for the old company that was no longer assigning clients to me (why?!). All these behaviors signaled that I was avoiding something but I didn’t know what it was, exactly.

One day, I plunged into the questions from my coach about creating a core message and vision for my business. No big deal, I thought. I love to think and write about myself. I am my favorite past time.

When I really started to dig into the work, all my inner demons came for a visit. I thought I had my core message all sorted out, but once I started answering the questions, I got confused about what I really wanted to say. Wrote myself into rabbit holes I couldn’t remember why I was visiting. I compared myself to others who look more successful, and I kept thinking “Everyone else’s message is better. They’re saying what I want to say, only better.”

The icy fingers of fear gripped my stomach and I spiraled down into a black hole of “This is a stupid idea. This will never work. Who do you think you are? That’s lame. No one’s going to want to do that. You don’t have anything to teach anyone.”

It was excruciating.

This spiral of indecision, anxiety and incessant self-doubt ranks high on my list of worst feelings. I felt it throughout high school, college, and graduate school. Every single time I had to write a paper for a teacher, I went through this process of not knowing: not knowing how the paper would turn out, not knowing if the ideas would come together in a coherent whole, not knowing if my work—and I—would please them.

For me, it is agony.

Being my own boss means I face this indecision and self-doubt every day. I’m examining, at the core, what it means to be me. What am I going to stand for? Can I make "it" (my profession, me) work?

During this particular spiral, I suffered through the negative thoughts: "I don’t know what I’m doing. I suck. This is too hard." I finally said out loud, to the dog, "This has got to be easier." I shut my notebook and took a break.

In the morning, I faced my notebook again, and it hit me: the reason I held on to that very-part-time-but-regular job was that it distracted me from doing this inner work. The job had kept me busy with concrete, well-defined administrative tasks that were “work” — but they weren’t the real work I needed to do to move my business forward. Blaming the distractions was far, far easier than doing the hard work of self-searching and then getting into action on my own behalf.

The worst thing about being your own boss is you. You have to face yourself and your inner demons every day.

That’s what I was avoiding: me. All those other rational reasons were smoke and mirrors to avoid looking deep within and asking, “Are you going to show up for your life or not?”

It means owning who I really am. Nothing is scarier — or more rewarding. I’m on the other side of this now, and life has gotten a lot more exciting.

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Portland, OR

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