Update on the 100 Conversations project: 1 down, 99 to go! I’ve got 4-5 more scheduled this week. As I dust off my editing hat, I’m excited to start putting these into future editions of the newsletter.
Until then, here’s my fresh essay of the morning. Have a great week creating-
As I sit here at 10a on Monday morning, it's already been an eventful day. I was going to write about something completely different I'd outlined and planned over the weekend. But, something else has been claiming more of my attention and I think I'm gonna talk about it head on instead.
If there's a single theme that has persisted in my life from my earliest memories to today, it's fear. Fear has governed my emotional energy, decision making, and creative direction for as long as I can remember. There's an entire future newsletter to be had there, so I'm gonna shift quickly into where it has been drilling me.
It's been 7 weeks since I departed my full time role. The title, benefits, salary, and equity. For the first time in my career I left without something else lined up, a backup plan, or runway of any sort. That's not a brag, to be clear. It's probably more on the cry-for-help end of the spectrum. The first month or so was effectively a detox of 15+ years of daily programming. Endless meetings, endless priorities, endless expectations, endless reasons to feel like the work ins't even close to worth it. (Yanking that out of my system is also a future piece all to itself.) The adrenaline that came with the freedom was explosive. And adrenaline has a limit.
As the high has worn off, the truth right now is I'm terrified. Not because I think it was a mistake. Not because I'm worried I'm going the wrong direction. I had all these big feelings and dreams and intentions, all of which remain entirely true and accurate. But time has allowed fear to creep in and question all of them. Every last one—microscope, lights, and exam table.
Here's what I'm noticing. I can clearly see this pattern where I work on multiple things at the same time. I've always been this way. I'm heavy on starting, never short of new ideas. I tell myself options are the right answer to fight fear. If I have multiple things going, they don't all have to work—just one. And wouldn't it be awesome if they all did?
In practicality, here's what it does to me: It gives me a reason to change lanes whenever I feel uncertain. It lures me away from doing uncomfortable things. It dresses up a distraction as a risk-mitigator. I can avoid sending that email, writing that post, recording that video by running over here to this other shiny thing I keep off to the side. Because the ultimate truth that I'm now faced with is:
When everything else is stripped away, is what I create and put out there myself going to be received as valuable? Are people going to get it? Will it strike a chord? Are they going to be confused? Roll their eyes? Or worse—not care?
More directly, because it has an eminent impact, the real question under it all is What am I worth? Without the contract, equity, paycheck, benefits, OKRs, direct reports, metrics. If I build something, do I really believe it will be effective enough to replace my salary and provide for my family?
As a way of ironic comparison, I spent the weekend on an extension ladder with an extension chain saw dropping some very large limbs from our oak tree. Definitely had a few close calls. I would say I had an angel or two steering a few as they fell. I wish one of them could explain my wife's favorite broken flower pot to her for me.
My point is, here I am without insurance or the more capable physical body I had 5 years ago, willing to be making some very real gambles with myself and my wellbeing. But I'm scared to record a 60 second video. To schedule that first session. To build that landing page. Why is the emotional friction there so much higher than real physical peril?
Earlier this morning, I had decided to change topics for this post like I mentioned. Then my wife and I sat outside with the dog and our coffee and I was processing a lot of this fear stuff with her honestly. (This woman is an absolute diamond I do not deserve. 23 years and counting.) Her challenge was simple and clear. "I only want to keep going if you're going to look back at this and know that you gave it everything and didn't leave any question."
Shit.
THEN, as if on cue, as I was checking my email I got one so freakishly on the nose I laughed out loud multiple times while reading. I've come to look forward to this particular author, but I had no idea the head on collision she had prepared for me.
"...this pattern exists where you already mustered up the courage to make the move, and now something is making you consider taking it back."
"...The question is not will you act. You've already moved. The question now is will you hold?"
"...It means staying in contact with what you originally decided to do, even when you're met with pressure to abandon it."
"We are in a moment that requires people who will not flinch... who have decided what they want to go after and will remain devoted in the face of obstacles..."
I feel like quoting any more than that is overdoing it, but you get the picture. Her own work, risk, and willingness to deliver on her creation met me right in the chest today when I needed it.
I'm going to wrap this up and go do some of those hard things I've been stalling on. Push through the fear. I hope you have one or two where you can go do the same.
-Justin


