Building Something Rather Than Talking About It - SDLN #1

Ok, settle in sports fans, this initial newsletter is going to be a doozy! It’s a bit long, but it’s a fun ride.

I’ve been building what most people refer to as “side hustle businesses” for pretty much the entirety of my working career stretching back now over 25 years.

I’ve always had something on the go either by myself, with my wife, or with a friend - I just find the process of building businesses fun.

Even when I was a kid, I was usually hustling - selling bulletin board software for the Commodore 64, writing and selling worksheets via mail order for stats tracking in video games, buying and selling sports cards…

If there’s a way to hustle and build a business, I’ve generally tried it - sometimes successfully, sometimes not so much.

🧪 I’m a Business Mad Scientist at Heart

My first adult side hustle was in my early 20’s back in 2001.

A friend and I got the idea of building a website that could sell physical video games online - basically, it was a mail-order business where you’d order a game on our site and we’d send it to you by mail or courier.

We were both technical and could write software, so the daunting task of building out a backend order processing system and integrating with the absolute earliest incarnations of credit card processing systems didn’t scare us.

It took us about 3 months, but we got there.

We’d sorted logistics companies, wholesalers for games, and even managed to get some free magazine advertising in exchange for help with building them a website.

The problem was, we were too early to market. That type of eCommerce was probably 5 years away. We also had the problem that delivery lead times for the newest games from us took too long - someone could hit their local game store on release day, pick up the newest game and play it right away, but if they pre-ordered from us, they’d get it two days after release.

After about 18 months, we got an offer to sell the site and our small inventory of games from another online game retailer for about $35,000 and we took it.

He and I tried another idea after that with a third partner, it did ok, but it was super high risk and when she offered to buy us out for $50,000 a year into it, I think we’d both had enough.

I never stopped building side hustles…

There were a bunch of bad ideas and failures along the way - SaaS products, Wordpress plugins, website-building services, apps… Like I said, I’ve tried most things.

But it’s always the successes and fun that bring you back for another bite at the cherry…

I built small hundreds of small sites from 2005-2010 that were doing AdWords arbitrage and affiliate sales - that was very lucrative.

My wife and I started and successfully ran an SEO and Content Agency for almost a decade from 2009 - 2018 - each of those businesses were doing six-figures at one point and we had over a dozen people working for us writing and doing technical SEO.

I wrote a book and built a paid physical newsletter/coaching business to over six figures annually from 2016-2018. During that time I wrote daily emails to my list for over 820 consecutive days - each email being 700-1500 words. I published over 2.5m words in that stretch.

😩 And Then Burnout Hit…

In 2019, I needed a break. My mom has passed away in Canada, I had a couple of health issues, and the grinding for almost 20 years with work and side hustles just finally wore me out.

I stopped experimenting… for the most part.

That’s not entirely true, I discovered Medium and across a couple of different accounts, I’d built out a pretty successful following and earned about $10k from 2019 - 2021.

I was still in the midst of burnout and while I enjoyed the writing as a form of escapism, it was the grind of writing so much over the previous five or six years that had basically pushed me into a sense of dread every time I stared at the flashing cursor.

So, I stopped.

I can’t lie, Covid lockdowns helped. They gave me an excuse to just not bother with anything and while content creators were building empires during that time with captive audiences, I rediscovered my love of video games and started playing more with my wife and (at the time) 17-year-old son.

It was escapism and it was beautiful. I dabbled with streaming and a bit of content creation, but I took a side hustle sabbatical.

☘ Lucky To Have A Solid Career

I’ve worked in Enterprise IT for my entire 25+ year career. I got in before the dotcom boom just when the internet started to become a thing for businesses, so my career exploded early and really, that kind of set me up for life in many respects.

I was making solid multiple six figures from my job by my late twenties and have remained that way for the last twenty years.

You don’t get rich by having a job, but you can get VERY financially comfortable.

Most people hate their 9-5 grind, but for me, I get to play with new technology all the time and solve really hard problems for some of the biggest companies, banks, and government agencies in the world - I really like what I do.

And it pays well…

I’ve never had the desire to turn a side hustle into my escape and as a result, when something becomes boring and not fun, I can shut it down - it doesn’t matter about the money because we’re not going to struggle to pay our bills or put food on the table.

That’s a luxurious and privileged position that I’ve earned, but I still appreciate nonetheless how lucky it makes me.

👀 The Itch To Build Came Back

Over Christmas, I started to feel the urge to “do something”.

It’s a familiar feeling… I want to create something, focus my attention, and then I immediately think, “how can I turn that into a business?”

My wife said the other day that she saw this coming about six months ago. After being together for over 27 years, she knows me better than I know myself.

I started looking around and I found a cohort of people who were writing and building writing businesses online… that intrigued me.

I lurked and studied on Twitter for most of January… started engaging and participating in February… and now, I know what I want to do.

I want to buck conventional wisdom.

I saw people saying the same things that people have been saying for nearly two decades:

“Focus on one thing and master it.”

“Learn one platform before you start on a second.”

“Don’t waste your money on tools and software when you’re just starting out.”

And all of these things are true in isolation for people who want to build a nice little online business that gets them out of their job. It resonates with people who are young, that don’t have much experience, and who are just learning.

But for me, it bores me.

I want to try something entirely different.

🧫 I’m Going Do Side Hustle Experiments

I don’t want to do one thing for two years and grind away at it in the hope that I can achieve an extra income stream that’s less than half of what I earn at work.

I’m 48, and that doesn’t interest me. I’d rather just play Call of Duty with my wife and son if that was what I was going to do.

No, I want to have fun and try some things - I want to experiment and challenge what people are saying.

And when I say experiment, I mean it - I’m going to follow a version of the Scientific Method.

I’m going to set up pages on the SeanDoesLife site for every experiment, write up each of those areas, outline my experimentation methodology, state my hypothesis for how I think it will turn out, then document the results over time, and finally come to a conclusion.

It’s going to be a “warts and all” view of the metrics and the effort that I’m putting in to achieve the results that I’m getting. You’ll see the revenue, the expenses, and where practical, some of the actual details of what I’m doing.

I also intend to be running several of these experiments at the same time - at the moment, by May, it’s conceivable that I’ll be running 5 different business-building experiments at the same time.

Take that “conventional wisdom”.

🚦 It All Begins Now

I started getting things in motion in late February when I settled on this idea with a view to starting for real on March 1st.

I’ve been putting some pieces in play this week and on March 6th, everything starts happening.

My intention is to do a normal “Sean Does Life Newsletter” once a week and then a second newsletter, probably Sundays, where I dive into something about the experiments that are ongoing.

Then on the first Sunday of a new month, that experiments newsletter will be a monthly review of where everything it, showing the numbers, and giving small status updates on where each one is… of course, the individual experiment pages will get updated periodically too and those will get linked in the newsletter updates.

I’m pretty excited. It’s going to be a lot of work and the risk is, I take on too much and nothing gets done properly, but that’s honestly part of the challenge for me.

This could either be a huge success or a huge failure, we’re just going to have to see what happens!

Either way, you can keep up to date via these newsletters and if you have questions or comments, feel free to hit me up on Twitter.

Talk to you soon,
Sean.