What matters is, you’re doing it.
and how a Canadian tv show taught me everything I know about taking chances.
Growing up I used to watch this show called Red Green. I have absolutely no idea how I stumbled upon it, or how it was even broadcast to me, given it was a Canadian public television show - but it was an absolute gem of TV programming. The general premise was there was this guy, Red Green, he ran some sort of lodge/cabin thing up in the great north (Canada), and the structure of the show was an oddly beautiful mix between (1) a Saturday Night Live style variety show, (2) a Home Improvement style comedy show, and (3) a This Old House style “do it yourself” show (In doing my Red Green research for this article, I also realized the show ran FIFTEEN (thats right, 1-5) seasons, and had over 300 episodes, spanning 1991-2006. For those of you keeping track at home, Red Green ran for longer than (i) Seinfeld, (ii) Friends, (iii) ER, (iv) Cheers, etc. etc. - impressive, right?) - and featured one of my favorite television segments ever: “Handyman’s Corner”.
The general premise of Handyman’s Corner is Red Green would invent seemingly unnecessary things in a Rube Goldberg-esque way, typically to less than desirable, yet ultimately entertaining outcomes - including such classics as:
Gull Wing Doors (where he uses garage door openers to put mercedes/lambo doors on an old buick skylark or something)
Bug Zapper (where he wires a radio transformer to a wall of screen doors to create a mosquito repeller), and
his Automatic Shop Door Invention, which opens with one of his best quotes ever:
“The smart handyman knows that your best projects are done alone, that way there’s no one there trying to tell you how stupid or impossible they are.”
Now, the overall (intentional) stupidity of the show belies some of the incredibly deep and important life-lesson-y points its title character makes, and this quote is no different.
Not necessarily that one must work alone, but that instead - when working on something seemingly so out there, so impossible, there will be plenty of people telling you it can’t be done. It won’t be done. It shouldn’t be done.
And that you must be the one that believes it will.
That you will be the one to make it so.
(trying hard not to go off on a star trek TNG tangent here)
Some of us are lucky enough to find others that believe in our vision so deeply we can create actual companies around them - others, must venture alone for some time before our peers begin to see what we see.
Regardless of whether you go alone, or go together - the very fact that you are going - is the important one. That you believe in your vision, and won’t let anyone stop you from achieving it - even if that vision is creating a mobile refrigeration unit out of an old chevy conversion van.
Enter our Neatworking connection for this week: John Montague (Managing Attorney, Montague Law)
John has been one of my good friends for some time, and we share a lot of similarities. We both graduated from UF Law during the height of the great recession (gone were the days of law graduates exiting their 2L summer associate position with multiple job offers heading into their 3L year, having heard numerous stories of those just 5-7 years ahead of me being wined and dined on yachts jetting around Tampa Bay or expensive bottle service at exclusive Miami nightclubs, and here were the days of “don’t try and calculate what your annual salary amounts to in dollars per hour or you’ll want to quit before you start”) and we both were interested in pursuing careers in technology, a path previously limited to those Stanford and Berkeley grads plugging away in their mirror-faced glass offices along Oregon expressway in Palo Alto, and away from the typical Florida-law-grad shuffle into one of those personal injury firms you see on the side of buses or telling you their names on the television) (I promise I don’t mean to knock on personal injury attorneys in each of my Neatworking articles but…c’mon yall)
But looking back, perhaps it was better this way, graduating during a job crunch.
Using lack of (job) supply to drive our true (job) demand.
Being free to pursue the ultimate vision of our career without fear of regret, without concern of leaving something better behind, without concern of failing, without lofty south florida law firm salaries being left on tables (not that I would have gotten any of those offers btw, I certainly would not have, but for the sake of this article, lets just believe I would).
Creating a path truly your own.
Even if we didn’t know how we’d get there.
Or how many times it would take us to get it right.
Unencumbered by the benefits of a good economy (lulz, would have been nice tho), ready to work, ready to try, and whether we knew it our not: ready to fail.
Ready to just get out there and DO it? Awesome, let’s go!
Take one look at John’s Linkedin and its pretty clear what his Handyman’s Corner segment would have been about: Blockchain
(talk about an even more niche career dream than mine which I describe as “tech stuff, in general, I guess”)
It’s John’s passion. And what I love about it is, it’s ALWAYS been his passion.
Like, not the “i’ve always been passionate about it…since all my friends started posting about it on facebook” kind of always been passionate about it.
But the “i’ve always been passionate about it…since it was only available on the dark web and you had to send someone a check and get back a usb drive in an unmarked envelope from them” kind of always been passionate about it.
I remember a morning maybe a decade ago, talking Bitcoin with John over an egg sandwich at Dunkin Donuts on University Avenue in Gainesville Florida (the nexus of all cutting edge technology, apparently), right around the time my roommate and I were debating on putting $1,000 of our own money into bitcoin (almost 100% of my net worth at the time btw, and a move that would have solidified my future as definitely not writing these articles right now and instead flying my military-decommissioned F-14 tomcat to my private island off of St Kitts & Nevis. Oh you think they dont have private island that can support an F-14 landing strip for sale off of St. Kitts & Nevis? You’re looking at Google maps and still not seeing any? Well, not unless you have private fighter jet money, they don’t.) But anyways - my financial foibles and missteps aside, John has always been into this stuff.
The company he was legal counsel for right out of lawschool (also, a pretty amazing achievement in and of itself, btw), now defunct music streaming giant Grooveshark (think: Spotify, but not nearly as “legal”, also a Gainesville company btw) was even one of the first businesses to accept bitcoin, back at least nine years ago - and he tells stories of his own group of friends mining and trading crypto in the early days - before robinhood, before coinbase, heck even before dogecoin (can you even imagine a time before DOGECOIN?)
Here was John - despite a great recession, graduating from a non-silicon valley-feeder school, and living in north florida - pursuing his passions, previously a dream many may have called stupid, or impossible: working in tech, actively involved in blockchain, and making his vision a reality.
Let the good times roll, right? Well, kind of.
(Remember how I said “now defunct” music streaming Giant?)
Enter: defunctness.
Some may have seen this as a failure. A sign he should turn around and head back to the well trodden path of the rest of his legal peers in Florida.
What was John to do? Relegate himself to a Morgan & Morgan commercial like his contemporaries? Or take the Red Green route - create his own project. Invent his own future. No matter how crazy, or ridiculous it may seem.
Obviously we know the answer, because Neatworking isn’t about relegating one’s self.
John began constructing his own future, this time, alone. (how Red Green of him)
He recounts his early post-Groove shark days, spending 10+ hours on the phone with referral services like RocketLawyer, just trying to land one new client.
Where conversations weren’t “here’s what you’re going to pay me” but instead were “well what CAN you pay me?”
Hustle Mindset. A common Neatworking theme.
“Give me everything and pay me anything”
I remember having similar days in Florida - running my own shop just like John (to much less success, I’d add) - driving to numerous incubators, networking events, meeting people for coffee - all in 98 degree weather and 100% humidity (how can there be 100% HUMIDITY? I’ll never know…) wearing a collared shirt and slacks (gross) - trying to convince people building something innovative that this fresh faced 2 year post-graduate attorney could provide them the same legal counsel that the big name firm they just spoke with could.
Grinding for legitimacy. All the good ones do it. Regardless of field.
Rarely do we stumble our way into legitimacy. Some may - they will go off and join an established company, nab a cool title, and some cache will flow with that - but much more commonly, legitimacy is an exercise in stacking blocks. Accruing small wins. Piecing together your career, and yourself, as you go.
Success is a long climb. Another common Neatworking theme.
And the one ever present Neatworking theme among all individuals I speak with, John very much included: putting yourself out there.
“I’m just gonna figure it out” says John as he speaks longingly of his early days starting his own practice.
And its true.
And he is.
The real Handymen/women/people out there want to figure it out themselves.
They’re excited to figure it out themselves.
Whether they’re pushing back on securities regulators regarding a new ICO, or they’re adding corrugated steel tracks to an old chevy caprice to make a pothole proof car, all operate with the same mentality: sure, it may sound crazy, but i’m going to figure it out, and i’m going to do it. Just watch me.
And this doesn’t mean we do everything perfect the first time. We just have to be ready to do it. And do it again. And keep doing it again until we get it right.
“My failures are what have made me good at my job” says John.
A lesson I think I’ve learned in every job I’ve ever had.
A few companies back, at a finance/legal/ops organizational meeting, all of the leaders were presenting their OKRs (Objectives and Key Results, not to be confused with KPIs (Key Performance Indicators) not to be confused with KRAs (Key Results Areas) not to be confused with KRIs (Key Results Indicators) blah blah blah…) and statuses against those OKRs. My time came and after the normal pomp and circumstance I always bring when discussing my own work I proudly displayed an OKR list full of all dark green circles. (Dark green is good, light green is OK, yellow is not great, red is…well you don’t want red up there). I thought I’d blow everyone, including the CFO, away with my progress. But instead - publicly - the CFO called me out on my goals. Noting that “if you’re doing everything perfectly then you’re not pushing yourself enough” (paraphrasing, I’m sure, but its how I remember the quote)
Make mistakes. Get things wrong. It means you’re pushing yourself.
And don’t be afraid at making them, and making them publicly.
(Or else be ready to get called out on them publicly, like me)
We need to be ready to put our name against our work, if we say or do something - we have to stand by it.
Don’t be sacred to fail. You might. But who cares?
Push yourself.
Don’t be scared to make the call. Be proud you’re able to make it. If you’re wrong?
Well, now you know for next time.
“You can’t enjoy the successes unless you’re also responsible for the failures”
And John certainly owns his failures, laughingly recounting stories of participating in plenty of ICOs, shorting blockchain offerings, and coming out the other end not nearly as wealthy as he could have been (been there).
“but I learned a lot”, says John.
Yep - that’s where the learning is.
And ultimately, we need to surround ourselves with people that encourage us to do just that, make the calls, fail, and be there for us when we fall.
When I think about the teams I’ve worked with in the past, or the people I’ve called my friends throughout my life - the truly great ones are the ones that encourage me to push, to take risks, to be bold - and that I know will be there for me if I fall.
And conversely, the truly…less than great...teams, people, are the ones that are just happy with the status quo. Aren’t willing to lean in - aren’t willing to take risks - would rather let someone else be bold. And are perfectly fine letting others fall.
Well - fine, I’ll be bold. John will be bold.
And we can be there for each other, and all of you other risk takers too, when we fall.
Regardless of how many times, how many iterations, how many hours on the phone w/ Rocket Lawyer it takes - we’ll do it. And we’ll keep doing it.
Ultimately that is the lesson Red Green is trying to teach us here, not that we can make a higher performing car engine with an old toilet, or that we can make an automatic table cleaner with an old window blind, but instead a much more philosophical point (because at Neatworking its ALWAYS a much more philosophical point): that we can always try. And next episode, we’ll try again.
Humans were made to try. And we were made durable enough to fail.
And isn’t that the fun part of life? Trying?
Think about all the times you tried something new. I bet those times, good or bad, come up in conversation, in memory, way more than the time you did the thing you’ve always done, in the same way, one more time.
So get out there, and do it. And fail. And do it again. And fail. And you know what, do it again. It doesn’t matter what it is. What matters is, you’re doing it.
“Measure once, and cut as many times as you have to.” - Red Green