In Defence of Half-Assing Things

I have a confession: I’m a half-ass entrepreneur. Or at least I was. You see, I started my business (freelance writing) as a side hustle. I refused to work with clients I didn’t like. I refused to pitch myself for business. And I more or less refused to take client meetings. None of that really appealed to me. I wanted to write and get paid. Interestingly enough, that’s exactly what happened.

Without knowing it, my “laziness” turned into building a freelancer inbound funnel that brought clients to my door. Within 6 months of starting my freelance business, I matched my job income. I decided to keep it a side hustle for two years before going full-time. After going full-time, I wrote my first book in under three months - and it hit the small business bestseller list.

I don’t mean to humble brag. I am grateful for the successes I’ve had to date, and yes, I did work hard for them. But it didn’t start that way. And honestly, I don’t think I’d have achieved much success - or been willing to put in much hard work - had I not half-assed things in the beginning.

This is my defence of half-assing it.

Let’s talk about school for a second

I want to address what some people assume about me when I share this story: that I was a burnout in school, doomed to laziness for eternity and somehow I got lucky.

Not so. I was an absolute keener. I wanted straight As (and my parents expected that of me). I ran a volunteer kitchen for low-income students and was a varsity athlete. I continued this vibe throughout university as well. I was a recruited athlete, landing a place at Yale University to play Ivy League varsity sports. I did, as well as doing way too many other things, and somehow got through with good (enough) grades. Not a “gentleman’s C,” but I didn’t have any Latin honours either.

I was good at the structure of school and sadly got too good at playing the game of academia. I don’t claim to be the smartest person. In many cases I barely learned anything except how to game the system to get a good grade. Sorry if you were my classmate. I was a brat.

Awaken to reality

Then something nasty happened. I failed.

Not in school, but in life (melodramatic, I know. Let me explain). I left college and joined a semi-prominent research consulting company in my native Toronto. After a year of doing - gasp - a job, I wanted to start a business. I figured I could game that system just like I gamed academia all the way to the top. Oh boy, was I wrong.

After leaving my full-time job at the ripe age of 23, I was going to make it big in my fancy new startup. Instead, within a year I had (in no particular order) gained 50 lbs, re-ignited an old sports injury, got depressed, lost most of my money, found myself in $14,000 of debt, and had no job prospects. One might call this a quarter life crisis, though looking back I’m grateful because it helped me develop my personal development system I affectionately call My 5 Fucks (it has nothing to do with porn - it’s just the “5 things I give a fuck about”).

Post-failure of my first startup, I was shaken to my (lack of) core, fat, and broke. So I did what any rational person would do: drank a lot. Just for a few days, feeling sorry for myself. Then I started looking for a job. I found a part-time gig with a nonprofit that just about covered rent, but they provided lunch every day so at least I knew I’d be fed. A few months later, I found a job at a startup doing customer success.

If it ain’t money, then wrong number

With my job, I had one goal: get out of debt. But I wasn’t making enough to pay rent, pay debt, and focus on my health (hi, dollar menu). So I thought about side hustles. That’s when someone offered to pay me for my writing. It was April 2017, and the man literally said “can I pay you to write for me?” to which I promptly said abso-fucking-lutely.

My side hustle became my means of paying for a personal trainer, which was steep at about $800 per month. So I had two rules for my side-hustle: it had to pay. None of this “for exposure” crap. And I had to be able to do it quietly, since technically I wasn’t allowed to take on any work outside my job per my employment contract.

The restrictions I had on earning money (and my desire to circumvent those restrictions) became my half-assing it. I wouldn’t chase big deals that required multiple meetings because I couldn’t take client calls at work. I wouldn’t do projects with picky clients because I didn’t have the time to respond to their emails. All my clients thought I was a full-time freelancer and my employer had no idea I was freelancing - and I intended to keep it that way.

Stop trying, start doing

As my business grew, it got harder to hide, but I managed. I took client calls on lunch hour or went for “smoke breaks'' (I don’t smoke, but no one questioned me. It helps to appear semi-erratic anyway, so people just go “oh, you!” when you say something weird like that you’re taking a smoke break even though you don’t smoke).

Eventually, I got to the point where I matched my salary in freelancing revenues. That was a fun month. I paid off a huge chunk of my debt, happily paid my personal trainer (I’d lost 7 lbs that month anyway so I was feeling good), and even put some money into savings. That’s when I started thinking about how to systematize my business even further. Use technology to take up some of the tasks I couldn’t afford to delegate and get even more strict about only taking on clients that were easy to work with. It got fun.

By the time I took my business full-time in January 2019, I had a bunch of helpful systems in place - a steady (if small at the time) stream of clients, some reputation, a portfolio, and now a heck of a lot more free time to build up my client base. I figured if I matched my job income with a side hustle, I’d easily be able to do it with full-time effort.

That’s when I stopped half-assing and started whole-assing. I’ve been happily running my business full-time since 2019. In 2020, I more than doubled my 2019 revenues.

In defence of half-assing it

I like my whole-assing right now, but I’m self aware enough to know I wouldn’t be here if I tried to whole-ass freelancing from day one. And I know I’m not totally unique. Had I tried to whole-ass it from day one, I’d have put in this burst of energy, quit my job (maybe), tried to secure big contracts, taken clients that sucked just for the money, hated my life, probably not made much money anyway, and quit. I know this because that’s precisely what happened with my previous startup. And I was not going through that again.

Instead, half-assing at the time allowed me to build up an idea. To test things out. To try new approaches. And to build on my own terms. Those are all critical lessons every entrepreneur needs to learn, and I am so happy I had the privilege to learn those lessons while being paid by both my employer and my clients.

When you whole-ass from day one, you fall into the startup adage: it’s like jumping off a cliff and building a plane (or at least a parachute) before you hit the ground.

It’s a visceral and effective simile. But let’s be honest: no one wants to fall off a cliff even if they have the potential to build an airplane before crashing to their death. I’d rather just go to the airport and get on a plane I know is safe (or, you know, extant).

I loved that in my business I got to learn new things while earning money. Same for my job at the time. I didn’t have any comparison to steal my joy - I was making money! I loved that I could up my commitment at any time, something I did in 2019, and had next to no barriers to entry or barriers due to expectations.. There was no pressure, only performance and revenue. It, frankly, was a lot of fun and next to no stress. How many entrepreneurs can honestly say that about their first two years in business?

My simple proposal to you

If you’re thinking about that next thing, I have a simple proposal: half-ass it. If it’s a passion, you’ll find yourself being pulled more and more. It will happen, I promise. Or if it doesn’t pull you in more, perhaps it’s not the right thing for you to be doing at that time. I know that statement might be sacrilegious to you based on what idea you’re thinking about right now, but also remember I’m just a rando on the internet. You do not need to take my advice. But I hope you do. I’ve been through the ups and downs of whole-assing from day one. And let me say it clearly: it was mostly down days.

If you are going to whole-ass it, I respect you and wish you the best of luck. But for those who want a slightly less painful way to give something a shot, I look forward to seeing your half-assed attempts in the very near future.