Around friends and neighbors, I’m using the phrase “in between jobs” to describe my current employment situation. That’s a convenient euphemism to make it sound less bad.
Most people aren’t familiar with my business so they only see a jobless Dad of three kids married to a non-working Mom, dealing with a mortgage and the same suburban costs they struggle with.
I used the term “unemployed” the other day with a former co-worker and I sensed sorrow in his reply text message.
In a town where conversations often revolve around employment, I’m conflicted about my actual status.
Yes, I’m between jobs because I left a job and intend to go back to a new one. Yes, I’m technically self-employed because I work on a business that earns money. Yet, I was laid off and I’m looking for work. So I’m unemployed.
The way I frame my story changes depending on who I talk to. The truest answer is it’s a long story that only my family and a few friends understand.
Regardless of what it’s called, I like my status right now. I’m home every day. I make breakfast for the kids and take them to school. I go to the gym when l feel like it. Errands are easy.
My side business work is fulfilling and challenging. It makes money and has the potential to grow more. That’s exciting.
It’s all got me thinking… what if I don’t go back to work full-time?
For those new here, I lost my job of 14 years in early October when my project lost funding. I was always treated well, but my employment situation was never ideal. I hope to go back to work full-time in the new year in a similar field.
I miss the benefits and salary.
Even so, my plan remains intact to retire completely and never work again at age 55, one year before my Dad retired.
During this period of searching for a new position, I have time to focus on my side projects to set them up for future growth.
Working for myself, I’m under constant personal scrutiny. Whatever I manage to accomplish on any given day is never enough. There’s always more to do. More writing, more optimization, more tracking, more upgrading, and more organization. I’m trying to automate where I can. But my business requires manual work on my part.
On top of that, since I’m home all day, I’m under constant pressure to be accessible to my kids. When I worked in an office building, they couldn’t knock on my door to ask for a butt wipe.
Young kids don’t understand the concept of work. All they want is more time with Dad. Being more available is part of why I’m embracing this lifestyle in the first place. But balancing work and kids while self-employed is much more difficult than I anticipated.
Waking up early is more difficult too. Planning out my day is not as straightforward as I hoped. When I work during the day, I tend to justify that working in the evening and on weekends isn’t necessary.
Maybe it isn’t. But that feeling of not doing enough is always there.
My Biggest Fears if I Don’t Go Back to Work
As a sole breadwinner, I’m responsible for providing health and dental insurance for my family. Without a sponsoring employer, insurance is expensive. I want excellent insurance, not average insurance.
We are on COBRA for now, but it’s been a slow and somewhat stressful process.
Maybe this is something I need to get over. Plenty of self-employed people have good coverage for their families. For now, at least, I want this aspect of my life to be stress-free. Working for a good employer with excellent benefits would put my mind at ease about healthcare for my family.
Another fear is that the local or national economy will sour while I’m unemployed. This scenario would be bad for my side business if the market tanks and people stop reading about investing. And it would be difficult to find a new job.
At age 42, I’m not ready to draw down my wealth for the rest of my life.
A salary is a solid baseline. Any side income is gravy on top. This combination, I still believe, is the path of least resistance to financial independence for me.
But I may have that all wrong.
What Scares Me About Going Back to Work
If I go back to work, I won’t be able to work on my side business as much as now. My side business could be the real path of least resistance to financial independence. It’s a riskier venture, but perhaps the more lucrative one.
Going back to full-time work, in a way, says that I can’t make enough money as an entrepreneur. But I’m conflicted because this blogging business was never meant to be a full-time gig.
However, online businesses have a way of growing exponentially. Potentially. Not guaranteed. There are many risks and speed bumps.
My new job may require too many hours and I won’t have the time or energy for my side gigs. Definitely possible.
Another fear is I could go into worker ant mode and fall into contentment and lose my ambition.
But the most painful aspect of full-time work is the loss of control of my time. I love choosing what to do each day. Even though I always feel short on time, having the choice is a premium luxury.
Looking back at the last 14 years of my career, the hardest part of the job was the time commitment. The work wasn’t so bad. But 40 hours per week is a lot despite being normal. The full-time job prevented me from extended traveling. It prevented me from seeing my kids four mornings a week. And it meant that my work was ultimately making someone else wealthy.
The Happy Medium
Weighing everything over and over again, I’ve come to the conclusion that after some time in between jobs, I can position my side business to flourish and return to a healthy and lucrative nine-to-five career. I’ll need to be selective in my job choice so I am not overwhelmed by a full-time work commitment where I still have some control of my time.
Finding the right balance might take a while. I am at the point in my career when I can be pickier with employers because I don’t really need the job. Yeah, it would be tough financially not going back to work full-time if the business doesn’t thrive. But our savings and passive income can carry us for some time.
But I’m not ready to stop building wealth.
More than anything, the desire for good health insurance is driving the decision to go back to work. Until my side business income surpasses what I can make as a professional, I don’t expect that to change.
Now that I’ve been unemployed for two months, I’ve seen the challenges of being self-employed.
Actually living the self-employed lifestyle is a blunt realization that it’s not as easy as it seems. The challenges are real and many.
So far, this experience reaffirms that going back to work is the right choice. Though it hasn’t changed my broader goals of leaving full-time work in a few years and retiring completely at age 55.
When I do go back to the daily grind, I’ll be relieved to have the coveted benefits to support my family, re-energized to do good work, and intoxicated by the notion that it may be the last job I ever have.
Photo credit: Emily Morter via Unsplash
Craig is a former IT professional who left his 19-year career to be a full-time finance writer. A DIY investor since 1995, he started Retire Before Dad in 2013 as a creative outlet to share his investment portfolios. Craig studied Finance at Michigan State University and lives in Northern Virginia with his wife and three children. Read more.
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