The Self-Imposed Pressure to Be an Expert
On resisting the urge to listicle and tie tidy writing bows 🎀
The itch is subtle at first.
It starts when I see the blank cursor. Tell them something helpful! Be useful!
The urge to listicle grows stronger.
Be concise! Boil your knowledge down into something easy to skim and consume!
Wait a minute . . . what knowledge? Can we ever be so sure?
Something about online platforms elicits expertness, in myself as much as others.
I do have a drive to simplify and systematize to make similar moves easier for fellow small business owners, and a genuine desire to put my best foot forward.
But what’s going on with that back foot?
“Why do you always wear those silly shoes?” Michael asked, as my hand went to unlock the front door.
I looked down at my tired black leather loafers. “They’re the only shoes I can wear when it’s raining! Leave me alone!”
I bought them at an upscale Italian boutique1 during the Before Times, back when I:
Got hired by corporate clients to do things like in-person speaking and training
Was paid to travel to fun cities, and felt okay buying one new “professional” outfit for each, knowing I reside solely in athleisure-ware the remaining 98% of the year
Needed flats because my fancier stilettos killed me after long facilitation days
To be fair, Michael is our resident fashion consultant, and all the “cool” sneakers I have thanks to his curation are pale pink or off-white, ones I wouldn’t want soggy or ruined by dirty gutter backsplash.
I packed into the train with other commuters shoulder-to-shoulder. Every fall, the collective clothing decisions make their annual shift from bright to drab—from splashy attention-seeking summer garb to practical browns, blacks, and greys.
A woman sat down next to me wearing calf-high strappy combat boots, shiny black hair in a shoulder-length angled bob.
I kept to myself, not feeling particularly energetic or talkative. As she stood to exit a few stops later at Times Square, she said softly, “I like your shoes.”
“Thank you so much!” I said, smiling and a bit caught off guard.
I didn’t tell her I bought them in Paris, or that I superglued the soles back together because they are falling apart.
Best foot, back foot.
In 2012, I taught a $79 five-week course called Build Your Business. One participant said that after the first hour, it had already surpassed the value of a course she had paid $2,000 for.
Still, I shut that stream of income down almost as quickly as I had set it up. I felt like a fraud, like I didn’t know enough yet.
Yes, I was happy to share my journey being a few steps ahead, but I wasn’t ready to wave any sort of expertise flag. And why should I? There was a far bigger, flashier course already on offer. What would be the point of adding clutter with mine?
“I’m not the end-all-be-all expert on this topic,” I repeat often in podcast episodes. “This is not the way, this is just one way, and I’m sharing what I’ve learned along the way.”
I see myself as the friendtor, the business bestie that you’d call if you had their phone number, delivered via podcast. What do you think? What have you tried? What have you learned the hard way? Or the short way, from people even farther along?”
I still veer toward teaching, which puts me dangerously close to the expert bucket. Teaching is something I have done since my earliest days, when I used to play school with my younger brother. I loved creating lesson plans and worksheets for him, sharing what I learned in my third- and fourth-grade studies so that he could have a leg up on his.
When I first started this Substack, I worried about jeopardizing my financial prospects by sharing from the “wound” and not a shiny, well-worn scar.
And yet, speaking honestly from the heart has always been one of the biggest gifts I feel I can give to the world. As my friend
said in a conversation for the Pivot podcast, “Whatever comes through me comes for me first.”
Sometimes when I open my Substack inbox, I start noting all the examples of people who can write more skillfully, with more academic rigor, or with even more honesty.
Part of me is scanning for the reason I will fail, or at least fall short. Part of me is still holding the measuring stick, the qualification bar, higher than my hands can reach.
There’s a gap between our taste and our talent, Ira Glass famously said.2 What about the gap between our talent and our truth? Between our truth and our published work?