It’s 5:37 am on a Monday and I’m staring at the ceiling. It’s still shrouded in the darkness of pre-sunrise yet glowing in blue light cast by one of the devices somewhere in my room incessantly making its presence known.
My thoughts default to someone at work pinging me in desperate need of help. Because, you know, I’m important. Even at 5:37am.
Except I’m not important to them anymore.
This isn’t a normal Monday.
It’s the first in a long time I’m waking up to a day where no one’s looking at me. No one’s watching (if you exclude my wife laying seven inches from me. But, going by the snoring, she’s still asleep.)
Three days earlier, on Friday, I decided to hang up the boots on a four and a half year tour of duty at a hyper-growth startup in Seattle. I began there in senior roles alongside our co-founders and CEO when there were 25 people and we used empty boxes as desks. When I left, there were 500 folks and we’d just achieved a US$1B valuation. And we even had proper desks.
There’s nowhere to hide when you work at a startup. Someone’s always looking. Your direct reports. Your boss. The board. Your customers. The creepy dude across the hall. Someone.
There’s greater inspection than in many “normal” jobs. Startups are often built on the concept of radical transparency. It’s an effective means to stave off unnecessary internal politics which can be an anchor dragging down progress and innovation.
All this looking and inspection and transparency isn’t to be feared. You could think it’s all a bit “micro-managery” but — in a company with a great supportive culture — it’s quite the opposite. It’s empowering and motivating knowing everything you do is highly visible, important and impactful. It helps you be at your best.
But now, as of this particular Monday morning, no one’s looking.
Your mind explodes with delicious visions of what life would be like if you weren’t working in a job. Lip-licking thoughts of sleeping in, cooking huge hearty breakfasts, sipping lattes while people-watching, grabbing a massage and having an afternoon kip.
Being your own boss — whatever that means.
The hard truth is this: if no one’s looking, it’s very easy to simply do nothing. Sleeping in and sipping lattes is only going to get you so far before you…well…become lazy and large, I guess.
And maybe depressed.
Depression is in my family so it’s something I try to remain self-aware of. In Australia, there’s a popular mental health campaign encouraging people to “act, belong, commit” in order to maintain strong mental health. Being part of a growing startup with a ton of transparency is a great proxy for this. You act because you’re part of something you deeply believe in; belong because you’re deeply embedded in a tight-knit team; commit because there’s transparency around the challenges you take on — everyone’s looking.
If no one’s looking, you’re left with looking at yourself in the mirror. Great for grooming the inevitable don’t-have-to-go-to-work beard, plucking the mid-forties grey hairs and basically admiring what a good looking rooster you’ve become.
But mirrors aren’t, by design, transparent. They offer only a reflection — you see what you already know. No one’s peering through and providing feedback, reinforcement, encouragement, and guidance.
No one’s providing motivation.
Running into an idea
In anticipation of this, I got up shortly after 5:37 am that Monday and went for a run. I didn’t listen to my typical picks of nineties hits playlists or the “How to be awesome at your job” podcast (I have no affiliation with the podcast, I just think it’s great!). Instead, I thought about how to be at my best at the beginning of my new journey — where I find myself without a traditional job for the first time in twenty-plus years.
How could I stay motivated and make sure I wasn’t going to slip into a sleeping-in latte-sipping spiral of doom now that no one was watching?
“The business strategies employed by highly successful start-ups and the career strategies employed by highly successful individuals are strikingly similar,” says Reid Hoffman in his book “The Start-Up of You”.
Hoffman’s insight bounced around my head as I was gasping for air at around mile three (I hadn’t run for a while). “If that sense of everyone looking — of transparency — was such a source of motivation and accountability within my startup experience why couldn’t I replicate it in my personal life?” I thought somewhat incoherently as my heart rate hit 188bpm — 10bpm more than what’s considered a safe max heart rate for my age and probably why I was merely shuffling on the spot at that point.
Back at home, I threw my shoes off and started icing my calves (OK, I hadn’t run in a really long time). I’m not certain what the early morning run had achieved for my fitness but it’d certainly unlocked an idea to keep my mental state in check.
I needed to invite people to look.
Open invitation: Look at me.
It began with a LinkedIn post. In it, I updated folks on where things were at and made a couple of claims about what was next for me…at that point I wasn’t even sure so I simply said “concentrating on having many great conversations, to learning even more, and to seeing what come of new connections and ideas.” Now there was something out there — some intentions I’d stated publically. Something to be held accountable for. It was the act in “act, belong, commit.”
Immediately I felt a sense of people looking and it motivated me.
In an early-stage startup, you tend to overshare information to force clarity and look for opportunities for efficiency. When everyone knows what everyone else is doing it avoids double-ups and creates collaboration — and keeps you accountable.
So, in the same post, I invited people to reach out, to chat, to follow me, ask me questions. I wanted to share as much as I could with as many as I could. Inviting people to look — inviting inspection — forces you to have more clarity. You can get away with kidding yourself with half-assed ideas and throw-away promises but not so much when under the scrutiny of others.
Actually, just like in a startup.
I’m not going to lie to you. My phone and inbox didn’t exactly blow up with folks fighting to get to speak to me first. It was more of a steady trickle, like when you need to turn the almost empty honey bottle upside down and wait for gravity to do it’s thing. Slow, but worth the sweet taste in the end.
So I proactively reached out to people, too. Some were in my network, some were people I targeted based on their experience and story. In my mind, these were my direct reports, my boss, my board, my customers. People I could be transparent with and invite them to look. It’s led to many amazing conversations but each time I’m deliberate about doing one thing — trying to ensure agreement on some meaningful action.
I share my website or a draft article with my new “team member” and ask for brutally honest feedback. They suggest an improvement or an idea and I commit to getting back to them on it. I make a claim I’m going to build something or write something or provide them with something and we make a follow-up meeting where I’m expected to show that thing.
In return, I receive the benefits of being motivated, held accountable, receiving feedback, feeling important. Having an impact on someone other than myself. Acting, belonging and committing — keeping my mental health in check.
All the things you need to be at your best.
I woke up that Monday morning with no one looking at me. By the end of the week, there were a ton of eyes watching me — and I’m much better for it.