What If I Don’t Go Back To Work?

Being self-employed for the past few months has made me realize how difficult it is and made me further question if I should go back to work or not. 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.

Oh damn

he wrote.

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.

And you.

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.

We have multiple income streams and cash savings to get us through this period, so we’re not stressed or panicking about money. Though our cash savings account is shrinking and I don’t like that.

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?

Never Enough

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.

Not working for a salary puts a damper on my ability to grow wealth. I’m not contributing to retirement accounts and I’ve paused our college savings for now. Both actions make me uncomfortable.

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.

We can always move to achieve financial independence. And there’s always money in the banana stand to keep us going.

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

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  1. I think that’s the key, finding a new position that is a better fit for you and your family, and maybe not driven by the overall salary. When I found my new role in 2016, I took a paycut, but have a much better work/life balance, less stress, I’m 15 minutes from home, and overall I’m much happier. It’s not always about the paycheck. Good luck.

    1. That’s good to hear you have a better work life balance. I do believe it’s possible for me. The commute may not happen, but a lot of employers allow some work from home flexibility. I hope to have that as a benefit.

  2. fred ford says:

    To make self-employed really work – you need to leave the house.

    1. I hadn’t thought about it like that. But you’re probably right. I do leave the house some afternoons and go to the library to work. It helps me to focus on writing. I try to stay offline and just write. In fact, I should probably do this today. I read someone yesterday mentioning they need to go to a coffee shop to get anything done. Kids at home exacerbate the distractions for sure.

  3. There might be a middle ground on this. I see a lot more part-time opportunities with benefits available now than I can ever remember. You might be able to find something in your field for 20 hours a week that provides health insurance and would leave you more time for your businesses.

    1. That would be sweet. I haven’t seen anything like this in my field/local, but might be worth exploring further.

  4. Brian Feroldi says:

    This is why we save in the first place — to give ourselves options in the future. I love that you can be super picky about your next opportunity.

    Have you thought about just working your side hustle projects for a set period of time (like a year)? Yes, it might drain your funds, but that would give you enough time to figure out if you could make it work.

    Another option would be a part time job — say 20 hours per week. That would likely be enough to close the financial gap and still give you enough free time to pursue your passion projects.

    Good luck either way!

    1. Yes, I have thought about that. If I’m going to do it, now is the time. Yeah, if I went for a full year, I do believe I could grow the side biz further. I’m struggling with this. That’s a big risk, and I do believe the economy is at risk, so I’d hate to be out of work when things go sour. That’s speculation, but I guess I’m jaded from 2000 and 2008.

  5. There might be a middle ground for you… Working part time and be very picky on what position you accept. The longer you are not working the harder it is to go back to work.

    1. A middle ground does sound like a good option. However, with the industry I’m in, it’s not very common. Most employers are looking for a full-time employer. Plus, to get the desired benefits, it’s probably a necessity. If I do adjust my expectations and change my mindset, I suppose it is possible. Just not very common in the space. Being away for a long period of time could be a negative factor if I look outside of my expertise. However, I’m more valuable in a certain space and it makes a lot of sense to go back there. My knowledge will not become outdated. But the long I’m away, the less I will remember!

  6. RBD,

    I feel you on that middle ground. I also completely understand the fact when I work from home my wife will ask me to change the kid’s diaper. To provide the literal butt wipe…

    – Gremlin

  7. I’ve contemplated this scenario many times, and have two young kids myself. I think the deal breaker has always been the daycare / preschool costs we will have as outlays for another 3-4 years. We live in NoVa as well and half day schools can run as much as 10k per child per year (not counting what you do with them after noon each day). For that reason early retirement and / or reduced work schedules won’t work for us anytime soon. Of course, that adds more pressure to maintain full employment during these years as well.

  8. RBD –

    I am saving this article in my archives to go back to, as I am striving to retire early and be with kids, once I have them that is. At least when you are back at work, at some point, you will have a much different mindset than 99% of others – you don’t NEED the job, and just pick something that makes you happy. This is a great article and thank you for writing it RBD, I can really see the emotions & struggles of what you are going through.


  9. One possibility might be job sharing. An employer gets two part-time workers for the price (or a little less) than one, the partial payment for insurance is likely less than COBRA, you may lose some benefits like 401K but you stay relevant in your field. Just a thought …

  10. Interesting! I was sort of “laid off” in a way last year and have been self-employed full time since then. I’ve gone through conflicting waves as well. The first six months I spent frantically working for myself while searching for a job. The more time I spend away from “real” employment, the less I want to go back.
    I love the flexibility. I never did fit in the 9-to-5 box well. I don’t know if it’s a genetic thing or what, but the afternoon crash seems to hit me and everyone in my family harder than most people. Now that I’m self-employed I can take steps to mitigate it, or – dare I say – take a brief nap during the day to hit the reset button. The health insurance piece has been difficult. My first year of self-employment income was low enough that we qualified for subsidies so health insurance was affordable (even if the deductible wasn’t), but now I’m earning more than I’ve ever made before and it’s been a challenge to figure that out. I’m excited for when my husband graduates soon so he can get a job and get us on some cheap insurance!
    Good luck with your business. It is weird, isn’t it – thinking that it might be the last job you have? (and here I am, only 30 years old!)

    1. Notorious DEBT,
      Thanks for sharing your perspective. I guess I’ve fit into the 9-to-5 box for the last 14 years and it’s strange leaving it. Especially with kids. If it was just me, I’d be much more comfortable with not going back to work. When I do go back, yeah I think I can work another 5 years and call it quits, assuming I still want to at that point. I’ll still need to provide health insurance for my family and we plan to pay for college. Huge expenses that don’t go away. Part of that plan is growing the side business to both increase savings between now and then, and to provide cash flow in semi-retirement mode.

      Awesome to hear you’re earning more now with your side biz, even with the napping 🙂