We Haven’t Lost the House. (Yet.)


Five years ago today, I walked away from the highest paying job I’ve ever had. And a company-match retirement plan. And a comprehensive health care plan. And a guaranteed monthly paycheck. 

No, I didn’t have a massive head injury. I just wanted to take a shot at freelance writing.

In the years since, I’ve never come close to earning as much; my wife and I have had to find and fund our own healthcare, changing plans multiple times; and we’ve also struggled to put money into savings, all the while trying to make enough to pay the mortgage and keep the lights on.

I’ll be honest, it’s been hard. At times it’s been scary. Heck, sometimes it’s been downright depressing.

And you know what? I wouldn’t change it for the world. 

Here’s why:

  • Back in 2014, when I started working for myself, my daughter had just finished the First Grade and my son was looking to begin kindergarten. In the five years since, I’ve been able to watch them grow up and do things like walk (and sometimes skip) them to and from school hundreds of times. 
  • We’ve been able to go on three separate two-week summer road trips around the U.S., seeing 24 states and having experiences and adventures we never could’ve imagined. 
  • Without any set schedule, I can pretty much live each day however I please. I can mow the lawn or take a five-mile run at 10 o’clock in the morning. I can work at my local coffeeshop, the library, or even a park bench. I can take a nap anytime I please. (And I do. Sometimes twice in one day.) If I want, I can get all my work done by Thursday and spend Friday at the pool or with a good book on a bench down by the river. 
  • I don’t have to deal with any of those normal, 9-to-5 stresses: no morning commute, no Monday-morning meetings, no office politics. Best of all, I never have to wait for Friday in order to dress casually.

So you can see why I say I could never work at a “real” job again. I suppose I could be tempted, though, if the position, say…came with a six-figure salary, six weeks of vacation, and an absolutely-no-meetings clause. A nap room would be nice, too.

I’m not holding my breath.

Of course, being self-employed hasn’t been all sunshine and roses either. Several times over the past five years, my wife and I have panicked, not knowing if we’d be able to pay the mortgage. The only healthcare plan we can afford is one with a deductible so high we pretty much still have to pay for all of our healthcare out of pocket. As a reward for our ambition and work ethic, the government makes us pay our very own special tax. (Gee, thanks!) And at my current average annual income, if my calculations are correct, I won’t be able to retire till right around, oh…95 years of age.

All that said, on Monday morning, when millions of people around the country are getting in their cars to head off to the rat race, I’m sitting out on my front porch, sipping a cup of coffee and listening to the birds sing, as I set my own personal schedule for the day.

After that it’s time for a nap. Just because I can. ~

9 Responses to "We Haven’t Lost the House. (Yet.)"
  1. Amen brother. When I was fired from my last job, I thought my life was over. I did the Amazon warehouse gig, worked at The Home Depot, worked at Walmart and then, for a friend. I realized that “corporate” life was probably not going to happen again. Two years later, I am doing Lyft full time. At times it is frustrating, boring and downright stressful, dealing with bad drivers and pedestrians who do not pay attention. But I go out every day, seeing parts of Pittsburgh I’ve never seen before and meeting some great people.

    I still apply for jobs in my field, graphic design, but am finally realizing that my forever job will probably not happen. Freelance is far and in between too. I pay my own health insurance and sometimes can’t afford groceries. I realized, like you, there is an amount of freedom one has by not having a “real” job. Mow the grass in the middle of the week, sleep in, set your own hours, and do what you want, when you want. You can’t do that with a 9 to 5 job. Yeah, it would be nice to have that steady paycheck, have my insurance paid for, have a few extra dollars in my wallet and have meaningful conversations with fellow employees. I’ll probably work way past my 70’s at the current pay I’m earning now, but I press on, hoping that things will get better. Not having a “real” job was not by choice. Sometimes my world feels like it is collapsing but, I AM truly blessed by what I have and who I have in my life. Life is good, it really is.

    • Thanks, Jim. Glad to hear that you’re enjoying your Lyft work. It’s people like you who helped me build my writing career, and I am forever grateful to you. If there’s anything I can ever do for you, just let me know. Best of luck!

  2. I remember when you took the plunge. Congratulations, my friend!

    • Can’t believe it’s been 5 years since that front porch party! Here’s to us entrepreneurs! ; )

  3. I fully relate. I’m sort of like Jim, but I told my high paying job to shove it in February even though finances were and are tight. It’s retirement time and even without the high pay, I’ve got none of the stress, and possible I will search for a programming job from home if I need extra money.

    • Good for you, Bill! Best of luck in wherever your life takes you from here. ; )

  4. Glad it’s working out. Been following your posts. I’m retired now and trying to get a local history research/writing thing going. (Not in Pittsburgh area -not a competitor!) Keep posting!

    (FYI, I’m an old B&W hand – I had a partial square in the Superbowl pool decades ago, if that means anything to you and gives me any credibility.)

    • Thanks, Rory! And good luck with your writing. I’ll tell my dad I chatted with you. ; )