Last week closed another professional chapter for me. I’ve left jobs before, but this was my first firing. I wrote about my most memorable separation here:

Getting fired feels shitty. Even if you aren’t doing your life’s work at XYZ company, it hurts to be told to pack your stuff and GTFO. Whether you’re eight years old getting cut from a travel hockey team or a 38 year old getting cut from your job, being told that you aren’t good enough, stinks.

When I reflect on 16 years of being in the workforce, I realize that I’ve mostly felt lost. There have been a few gigs that felt good. At B.E. Retrofit working for the Colwells, mowing lawns for my uncle in the summers, being a coach at Mike Boyle Strength and Conditioning; these were good ones.

I seem to be missing the character trait required to “stick it out” at work. That first job at EMC in 2007 was a launching point for many friends and peers. A lot of them are now high powered sales leaders and executives that send their kids to great schools, live in nice houses, drive sexy cars, and take cool vacations. That could have been me too if I just put my head down and worked. I had too many questions. Why am I showing up every day if I hate being here? Does everyone else hate this? Are they just tougher than I am?

The most money I’ve ever made in a year is 126,313 and 42 cents. Last year I made 107,000. I don’t know if that sounds like a lot or if it sounds like pennies. I used to think, “If I can just make 100k, then I’ll be happy.” That hasn’t proved to be true.

To compound things, my personal finance habits are trash and I’m often upside down each month filling in the gaps with credit cards. I have a spreadsheet titled “monthly financials” that shows a negative number at the bottom of column B. I planned to fix that situation with hefty commission checks that never came. My lifestyle has crept into a spot that might fit someone making 220k. Amazon delivers Whole Food groceries to my doorstep, I lease a brand new truck, the house gets cleaned twice per month, I have a bad door dash habit, and haven’t figured out how to scale back my tipping since covid started.

This isn’t the first bad spot that I’ve put myself in. I’ve been here before. In 2008, I opened a gym. I like to believe that I was a great coach and a terrible business person. The gym lost money every year for the six years that it was open. I think we did a lot of great work for clients, but I’ve got nothing to show for it. During those years, I relied on my spouse’s income, lived off credit cards, stopped paying my student loans, and flinched anytime I handed my card over to be swiped at Dunkin Donuts. More than once the card was declined but they gave me the coffee anyway. The biggest difference between then and now is that I live on my own and share custody of two 5 year olds. I’ve got people depending on me to generate cash in a predictable way. The only time I’ve generated cash in a predictable way is working jobs that wilt my soul.

I’m in a painfully familiar place again, struggling to redefine myself professionally. All I know is that I want to control my calendar and do creative work. I’ve never demonstrated the ability to generate income without a job. That last sentence keeps me up at night. My anxiety is up a few clicks. The heavy weather patterns of depression are not far off. Some days, I hide under the covers and eat Chinese food straight from takeaway containers. Other days I can will myself to exercise, get outside, and bang out cold emails in search of work.

I’m trying to find ways to take small steps forward. I’m breathing fresh life into an old project. I put my housekeeper in a holding pattern for a bit, I’ll swap Whole Foods delivery for walking into Shaws, and I’ll consider deleting the DoorDash app or at least putting it in a folder that is not on my home page. 45 dollar pizzas are my meth. On days when I don’t have my kids, a little pot helps me de-couple from the existential dread.

I’m feeling a mix of fear about the future and restrained excitement about getting to decide how I spend my days.

If you have any thoughts, smash the reply button because I’d love to hear them. Thanks for being here.