Not Dad’s Retirement

Craig Stephens

MY FATHER RETIRED from a 35-year teaching career in 2002, when he was 56 years old. He hasn’t worked a day since. For years, his retirement was the primary model for my retirement aspirations—until I realized my path needed to diverge.

Like many dads, he worked a career he tolerated but probably didn’t love. It provided our family with a comfortable lifestyle in the suburbs of a low-cost-of-living city. Teaching enabled him to be ever-present during my youth, with summers off and time to coach my baseball teams. He took his pension and left teaching without hesitation when he reached retirement eligibility.

I missed his retirement celebration because I was halfway through a 14-month backpacking trip that took me to southeast Asia and South America. Upon my return, I was 27 years old, broke, unemployed and living with my parents.

Though my dating prospects were bleak, I had a finance degree and a few years of information technology (IT) experience in my back pocket. I was ready to return to the workforce. Inspired by my dad’s retirement, I set a goal to retire at age 55, one year earlier than he did, so I’d have the flexibility to travel the world again without the time constraints of salaried employment.

After six months of living with Mom and Dad, I landed a government IT consulting position in the Washington D.C. area, for which I was underqualified and overpaid. My salary snowballed. Backpacking the world trained me to live frugally. College finance courses taught me to contribute to my 401(k) and invest monthly surplus dollars into stocks. The foundations were in place to reach my retirement goal.

But one thing became apparent soon after I started my new job. I didn’t like government IT consulting. I worked on massive IT projects with hundreds of workers. My direct contributions rarely influenced outcomes or led to organizational improvements. I was a small fish in Lake Titicaca.

Job satisfaction was elusive. But I was okay with that because I mainly cared about the salary and benefits. The high earnings allowed me to save and invest to reach financial milestones. My IT career was the path of least resistance to early retirement.

A steady job and homeownership gave me the confidence to finally achieve some dating success. I married and started a family. Early retirement to travel the world suddenly became impractical for at least the next 20 years. But the desire to retire at age 55 didn’t go away. In fact, it strengthened because I didn’t enjoy my career and wanted to escape.

Like my dad, I tolerated a career I didn’t love to provide my family with a comfortable lifestyle. But unlike my father, I lived in a high-cost-of-living city, worked summers and had no pension waiting for me after 35 years.

In 2013, I discovered a creative outlet by starting a personal finance and investing blog called Retire Before Dad to share investment strategies, personal finance tips and my progress toward my age 55 retirement goal.

Our Free Newsletter

My website became a side business. I enjoyed writing and earning money without filling out a timesheet every day. Writing more than 400 articles helped me discover that my dad’s retirement wasn’t the right model for me. His retirement was the end of his active earning years. But I found earning money through self-employment was more rewarding than a salary, and I expected I’d want to continue earning beyond age 55. My retirement goal was ultimately about attaining freedom and flexibility in my life. I started admiring entrepreneurs and workers who built careers they genuinely loved so much that they didn’t want to retire.

At some point, all the diligent saving and investing over the previous two decades became a large enough financial backstop. Meanwhile, unproductive meetings consumed each working day. Career advancements meant I had to sacrifice more brainpower and control over my time. What I craved was independence, extended time off, more fulfilling work and control over my weekdays.

In late 2022, I left my 20-year government IT consulting career at age 47 to be a fulltime blogger. I’m not aiming to retire at age 55 anymore. I’m as excited as ever to build my business—because I now have greater control over my time and a more gratifying profession.

Blogging is location independent. I can work from anywhere. I control my workday hours. My success depends on the quality of my writing output, not some opaque HR performance metrics.

Retirement is the most logical escape from a tiring career. But many retirement-aged workers still enjoy being productive and earning money. The commutes, meetings, overbearing superiors, corporate annoyances and constraints of fulltime employment make us want to leave.

But retirement may not be the answer. My suggestion: If you’re in a career you don’t love, consider your investments as the foundation for your next life phase. You may not have saved enough to retire outright—but it may be enough to launch a second act.

Craig Stephens writes about personal finance and investing at Retire Before Dad and Access IPOs. Follow him on Twitter @RetireBeforeDad and Facebook.

Do you enjoy HumbleDollar? Please support our work with a donation. Want to receive daily email alerts about new articles? Click here. How about getting our newsletter? Sign up now.

Browse Articles

Notify of
Inline Feedbacks
View all comments
Gavin Schmidt
Gavin Schmidt
3 months ago

Criag, relatable and inspiring article. I very much enjoy my day job. However, it’s fun to have projects on the side that are enjoyable and generate some extra income.

Mr Moderate
Mr Moderate
3 months ago

Welcome, Mr. Stephens, to HD.
Your story resonates with me, my dad, and my son on many counts – I’ll bear you the longer version!!

3 months ago

Craig – Welcome to HD and thank you for your column. I do look forward to more and will browse your site. I started to work for in financial services right out of college and learned the value of compounding and all the rest very quickly. That mindset allowed me, my wife, and our 2 kids to take a break when I was 45 and spend a year backpacking around the world. While I did love my career, I was ready to move onto the next chapter so the timing was right for us and my early investing gave us the foundation to be able to do that. And that foundation will, thankfully, continue to fund future phases of our lives. Cheers

R Quinn
R Quinn
3 months ago
Reply to  Guest

Compared with average folk, are the key words “financial services”

Free Newsletter