Happy(ish) Holidays

My Own Private Prison

The hardest part about being a founder?

Believe it or not, it isn’t money. Don’t get me wrong, an empty bank account pretty much sucks and we will have plenty of time to get into that black hole later.

The hardest part is actually just trying to unplug my brain from work.

Can’t do it.

I’ve tried, but short of an Office marathon, my mind is always thinking about the business.

And why wouldn’t it be stuck in overdrive?

Companies have teams to collaborate, strategize and carry the load when fatigue sets in.

But what about the solo founder? When we face end of year burnout, the best thing we can often do is take a walk and get some Vitamin D. Because reality is if we don’t hold it together pretty much 24/7, we might not feed our kids.

So, December rolls around, and I do the whole stupid thing where I lie to myself and say I am going to take a few days off and spend it with my family and just try to recharge.

This is the year! I’m going to put up my out of office message and enjoy myself.

But what about customer issues? Running invoices? Outages? Well, I am customer service. Oh, and Accounts Receivable? That’s me. And I will let you guess who the IT Department is 👋. I won’t even get into who does all the outbound and recruiter at this joint.

I can never fully detach. Instead I carry this anxiety and dread around like a portable prison that lives rent free in my head (it sucks).

Yup, I’ve tried therapy like all of you. But I can’t change the feelings that live inside me. Sure, writing down lists helps, and I know we’ve all asked ourselves “what’s the worse thing that can happen”, but none of it matters if you can’t make rent next month.

It’s exhausting and it doesn’t go away just because it’s Christmas.

Office Holiday Parties

The Broke Ass Holiday Party was amazing. I had the entire Subway to myself on Friday night and dined on a Chicken Bacon Ranch footlong, two Diet Cokes (I Ubered), and went all out with the footlong cookie (time to let loose).

The funniest things occur to me as I get older. Take perspective.

When I worked in an office, I loathed holiday work parties. The cheap booze. The awkward conversations with coworker spouses while dining on tapas. Talk about a slow death.

But I miss them. Having an excuse to throw on a jacket and tie and hire a babysitter for the night. The conversations would vary, but I’ll be damned if I don’t miss standing around and talking shit with people. Those Zoom holiday parties just never hit the same, even as hard as managers would try.

Why do things always seem better on the other side? It might be longing or regret. Maybe we realized we might never get back what we had.

My theory?

It’s connection and the shared human experience. I’ve worked from home for the past 5 years and it’s just a feeling of isolation. Holiday parties and happy hours were a great opportunity to decompress and celebrate in a way that Slack just will never capture. A win is still a win, but sitting alone at the kitchen table when you sign that first customer is hardly the EOY extravaganza I was hoping for. We just give ourselves a pat on the back and go to Subway on Friday night.

But the footlong cookies are 🔥.

A Taste of Things to Come

After my post a few weeks ago, the outpouring of words and support from other founders in similar predicaments was quite frankly astonishing.

I heard many stories of founders working multiple jobs and hustling not to make their dreams come true, but just to make ends meet.

You humble me.

With each newsletter I want to highlight a founder and tell just a little bit of their journey. I want to shine a light on the underbelly of entrepreneurship, not to condemn those who might have a more linear path (it’s still a hard one), but rather illuminate and educate others to some of the grittier aspects of being your own boss.

There will probably be plenty of “oh fuck…” moments, but I promise there will be plenty to celebrate as well. More to come.

Love you all 💙,

-T

Vibe of the Week

Music in my head as I write this weeks issue.