Digital Writing

Why I Returned to Being a Solopreneur and Started Creating and Writing Digitally

And left a six-figure salary on the table

Before I started a family, I was a consultant and serial gig worker. In 2009, I got married and life took a different path. My wife and I met online. eHarmony. We were both running our own small businesses and single parents. We each had one young child, only 6 months apart in age.

We lived six hours apart. Our first date was on a ski hill. It was near the halfway point between us. Less than four months later we were married, moved in together, and had a third child on the way.

We both decided to step off cliffs of certainty. Why mess around — just get after it, has been our motto.

At the time, my consulting gigs required a lot of travel. I decided to ‘settle down’. I needed to be closer to home. I applied and was hired at a local community college as a project manager with salary, benefits and regular hours.

I was never cut out to work in an office — in a box. Much of my younger years involved working outside (forestry, fisheries, and tourism). Thankfully I worked with an excellent Vice President at the college and enjoyed the work.

I moved up the ladder quickly securing a job as the manager of an internal data team. Even though I am not a ‘data’ person. More of a people person. The bulk of the work was government data reporting. Not the most stimulating.

After less than two years, I was restless. I got a higher paying job with a healthcare organization. I moved up the ladder there. Within two years, I became a Director. Managing a relatively small team covering a massive geographic area (300,000 sq. km) — largely rural and remote.

When the COVID pandemic hit, I was in all-day emergency planning and response meetings for months on end. Almost six months. We devised an emergency response strategy for rural and remote communities in case of the need for evacuations. Only certain hospitals in the region could accommodate symptomatic or COVID-positive patients. Each of those had limited capacity and we had to plan for the worst, including possibilities of field hospitals and morgues at capacity.

As COVID slowed, I was restless again, burnt out, and tired of offices and cubicles. Not only had I been working full-on, I had also completed a doctorate degree in online education. I defended my dissertation in early 2021, after 5 years of pursuing the degree. Those were busy years.

In the spring of 2021, a head-hunter (search firm) contacted me about a director role back at the community college. I entered the competition and got the job. After 3 months, I realized I could not exist in a box anymore. No more cubicles, offices, and largely useless meetings.

The salary and benefits were excellent. The stability of these had moved us through the busy years of raising young kids.

But, something had to change.

The next step off the Cliff

After six months in the new position, I left. My wife and I had several conversations about possibilities.

For months I had been reading and studying the world of digital creation, digital writing, and online courses.

I have a doctorate degree in online education — but what’s going on out there in the world of digital creation and curation is astounding and impressive. Especially outside of formal institutions.

By April 1, 2022 — I was solo again. Back to the world of being a solopreneur. But not fully solo as I have full support of my wife. She is a mental health counselor and has filled the slot of full-time work in our household.

I do some part-time faculty work for a university, teaching Communications courses online. This is a decent supplement to take on the task of digital writing and creation full-time.

We’ve called this initiative: Box Cutter. We allocated 12 months for me to take a solid kick at becoming a digital writer and creator and begin to make the income I left on the table.

I’ve been soaking everything up that I can, while also writing and creating every day.

Cutting Boxes

This business of digital creation and digital writing takes time. Anyone in the Start-it-up phases will want to be prepared for the long haul. Overnight success is extremely rare. Patience and persistence are the name of the game. ‘Practice in public’ as some of the leading creators suggest.

My approach to this has been a full cliff jump — a full box cut. Others advocate for a slow, side-hustle approach. Many stay in full-time employment and do well for themselves through the creation of creative channels and profitable digital writing and creation.

For many years, I’ve had side hustles in addition to demanding full-time work. I’ve taught online for almost four years. I started with one course and a few students. That has evolved into three courses.

I also teach at the local community college on sessional (single term) contracts. In a human resources program with almost 100% International students.

So the step off the cliff is not into complete oblivion.

Taking Stock

As I set out, I took stock.

• I had been on Twitter since 2010. Not very active though. Largely news media articles of interest to a very small following.
• I had been on LinkedIn since about the same time.
• I abandoned facebook many years ago. Too much personal drama and silliness.
• I had kept various blogs over the years. The first I started was in 2006 using Apple products to share stories of my first kid as a baby.
• I then set up a WordPress blog in 2010. Mainly articles on wild Pacific salmon. I did some volunteer work for a remote Indigenous community that was active in salmon conservation work.
• Two years ago, in my professional work, I set up a draft course on the platform Thinkific.

I knew I could navigate many of the platforms. Now the creation and building audience part.

Starting it up

My main strategy of choice has been LinkedIn. Initially, I read everything I could that Justin Welsh — LinkedIn king — was producing. I agreed with his logic, strategy, and thinking. I knew the platform, and in early 2022 I had about 1,000 Connections.

I set out posting 2–4 times daily. I had a certain range of topics I wanted to explore and see how they landed.

I was also reading everything I could find that Nicolas Cole put out, along with his Ship 30 for 30 partner Dickie Bush. My reading and studying evolved from there.

Slowing it down

Things slowed for a bit in the early summer months. My mom passed in the late spring of 2021. Due to COVID restrictions, we were not able to do a service until a year later — June 2022. We also had a special small family gathering to spread some ashes at a special remote site in British Columbia.

I wasn’t writing as much online, but tracked my ideas and thoughts in a journal.

Her passing was a significant motivator in our decision for me to cut the box. We had traveled as a family to be with her in her last few days in the summer of 2021. It was challenging on various fronts, with COVID restrictions. Not all of my family was able to make it home, as international travel restrictions were in place.

Navigating the deaths of loved ones can generate a lot of introspection and reflection. My sister had passed of brain cancer in 2017, and all four of my wife’s grandparents passed between 2018 to 2020. Death was not new.

We knew I had to come up with a plan to get out of public administration work, and set out back on my own path. We only have so much time on this planet.

In our discussions, one day my wife said:

Increasing speed and content creation: “Practicing in Public”

Fast forward to the present day, and I am now 8 months into this box free gig. My LinkedIn connections have doubled. Now approaching 2,400 after starting at approximately 1,000.

My impressions have steadily increased sitting at about 5,000 per week. Not a lot compared to many with huge followings. However, I have consistently reminded myself — comparison is not the game. It’s a motivator, especially in celebrating other folks’ successes.

I have covered a lot of breadth in my LinkedIn posts. I have an eclectic professional background. I have been exploring topics to see what audiences respond to, as well as what I am enjoying creating and publishing.

In October, a colleague reached out with a small writing project. He had seen what I was posting on LinkedIn and asked if I could take on a small project. These were the first $ made online.

I started an account here on Medium in May 2021. I started sporadically. Followers came in a similar pattern. Single followers about a week apart. I kept publishing. Taking LinkedIn posts and expanding.

Initially, I would post on my personal website (research blog) and then bring them over to Medium. I stopped that process in September and published directly on Medium. I am now at almost 90 stories and 60 Followers. Just this week I have started to pursue writing within some of the Medium publications.

In September I also set up a page and newsletter at Substack: Box Cutter.

This week will be my sixth free weekly newsletter. Subscribers are trickling in, with plans to go over 20 this week and keep building. I appreciate the Substack environment as it has its own ecosystem and others on the platform can find you.

In the fall, I also established a YouTube channel.

I started with short ‘walking, thinking, talking’ videos. Talking about many of the things I also write about.

In early careers, I did a lot of work in community development. In Canada where I live, over 50% of the population does not have the literacy required for day-to-day life. Videos can be an excellent pathway through literacy struggles.

In the past 6 weeks I have also stepped up work on Twitter. This has mainly been far more about engaging with others. It is called ‘social’ media. This has made a difference in making quality connections and finding more builders. I am currently at 130 followers.

Nothing I have written or posted yet is seeking $. It’s all been Free.

Monetize?

I have not rushed into monetizing anything.

We did not have a large savings nest to get us through this gig, but a few resources to draw upon. I was also comfortable, that if needed, I could always pick up work.

I’ve read many recommendations from successful digital creators — build consistency, build trust, build content, then look to monetize. Don’t rush it.

I appreciate this approach. In the last four weeks, I have set up a Gumroad page.

Starting with small guides. These are available for Free or for whatever someone chooses to pay.

I have also set up a shell for online learning modules focussed on Respectful Communication. A course to assist in self-reflection and navigating conflict and disputes.

For the last several months I have shared components of the course in LinkedIn posts and short videos. This has generated valuable feedback. I plan to offer this for free initially, build some community, and generate more feedback.

What have I learned?

I have been tracking a lot of my learning along the way and sharing it. I posted a story here on Medium and Substack in early November comparing what I’ve learned to a doctorate degree that took 5 years and tens of thousands of $.

A lot of what I’ve learned is also shared by others that have become very successful in the world of digital creation. Sometimes it takes learning things for one’s self for those to become embedded.

• Be persistent and consistent.

Coming into this gig I had been writing consistently. It took me two years to write my doctoral dissertation. I was well past Draft 30 by the time I defended and published. But that was academic writing.

Writing online, and in a character-limited environment like LinkedIn, takes some practice.

• Don’t be in a rush to define your ‘niche’.

I am still working on this. I have an eclectic professional background and a lot of interests. My academic journey has been multi-disciplinary. I teach courses in an interdisciplinary manner.

• “Practice in public” is excellent advice.

When in doubt press “publish” or “post”. Some digital environments are more ephemeral and fluid than others. Twitter moves fast and furious. LinkedIn is not as fast, but still ephemeral.

Medium, Substack and personal websites are more like repositories. Find someone you enjoy reading, then search their content. For example, Alex Mathers is someone I have really enjoyed following. His illustrations and productivity are impressive. And he openly shares his journey.

I have also enjoyed Eve Arnold and her stories of working full-time and creating part-time.

• Diversify platforms, but not too much. Be social.

In recent months, I’ve engaged more socially within many of the platforms. I have consciously tried to keep it to just a few platforms. It’s too easy to get overwhelmed and pulled off track.

I have also read a few scary stories of creators getting put in “LinkedIn jail” for example. I’ve had one short blip there that gave me a fright. That was the impetus to diversify, and get the newsletter going.

What’s next?

Medium is a social environment. In the past few weeks, I have consciously and purposely dedicated more time to this platform. I have been engaging with more fellow writers and creators and sharing appreciation for good writing.

I have started looking at, studying and applying to Publications within Medium. An article was just recently published through New Writers Welcome. I intend to publish more through other publications.

In the past week alone, and even as I write this article, I have moved from 50 Followers to 64 (at this moment). My first goal is to reach that infamous 100 by the xmas season. Then onwards from there. I love to write, so this is an excellent ‘medium’ to do that (pardon the pun).

I publish my newsletter weekly which is part ‘journey tracking and updating’ — as well as a personal accountability mechanism for me. I share what my plans are, and this assists me to also ‘practice in public’ and public with what I’m setting out to do.

I set a goal to make at least $1,000/month from my digital creation and writing by December 2022. I made and surpassed that slightly last month in November. I have another small writing contract set up for December. These came from my work on LinkedIn.

The next goal is $5,000 by April 1st. That is the one-year mark of becoming Box Cutter. I intend to get there, similar to online creator Daniel Vasallo’s recommendations through a series of small bets.

Wrapping it up

The image at the top of this article is two of our kids in a very special place for our family. Up until COVID, for 12 years straight we traveled to the islands where I grew up, off the northwest British Columbia coast. It’s a long journey to get there. Close to 8 hours of driving, and a 6-hour ferry trip across open ocean.

Every year we would spend at least 2 weeks there. Most of the time camped on a beach, out of cellular range and with no electricity. These trips have been purposeful for building connection to place, to each other, and to each of our own Selfs.

The spot in the image is a rugged spot on the coast just up from the huge sand beach we camp on. Our family belief is to encourage adventure, responsibility, and exploration.

My heart is in my throat when our kids are in places like these cliffs they’re sitting on. But at some point, they will set out on their own life journeys without parental influence and ‘control’.

This journey of returning to soloprenuership has been similarly motivated. Our kids have known for years, I hate office-based work. They have noticed and shared the changes they’ve seen in my mental (and physical health) since setting out on this journey.

They also know the risks.

But that’s also why the term solopreneurship may not be a full fit — as this has certainly been a group effort.

My hope is that just as they find comfort to sit on a precipice, they will see that it’s OK to step off the precipice (in a metaphorical sense).

We can’t buy more time in our lives, but we can sure be purposeful in what we do with the time we have.