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Home»RETIREMENT»Lifestyle Dividends – Retire Before Dad
RETIREMENT

Lifestyle Dividends – Retire Before Dad

Editorial teamBy Editorial teamAugust 29, 2025No Comments6 Mins Read
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Lifestyle Dividends – Retire Before DadWhen I’ve written about dividends over the years, it’s been about cash payouts from stocks, funds, and alternative investments.

But dividends can be more than just money hitting your brokerage account.

Years of saving, investing, and running a business now pay a different kind of return:

Lifestyle dividends — the freedom, flexibility, and opportunities that come from building a sufficient financial foundation and solo business.

Sometimes it means being home for a mid-day school event or choosing uncommon work hours.

This summer, it meant a trip to England and Scotland with my family. 

For three full weeks, we visited historic castles and world-class museums, explored the Scottish Highlands and dramatic landscapes of the Isle of Skye, and had countless hours to just be together as a family.

What made it especially meaningful for me wasn’t so much the trip itself, but how it was possible. 

Financially, we funded the trip through a combination of credit card points, stock and ETF dividends, savings, and business income rather than a salary. 

Without an office job, I don’t have to ask permission or plan around project dates or a client’s agenda. I could run my business on the fly. 

The destinations were incredible, and we have more adventures in the pipeline.

But the greatest dividends come from the extra time and unforgettable experiences with my kids — made possible by self-employment and decades of investing.

The Journey

During our U.K. trip, Mrs. RBD and I would occasionally make the mistake of saying, “After this, we’ll get ice cream”.

Well, “this”, of course, quickly became very boring — even if we were in one of the world’s best museums or an 800-year-old cathedral.

The kids often wanted to be at the next place instead of enjoying where they were.

On our travel day from London to Edinburgh, engineers caused a power outage, stopping all inbound and outbound trains from King’s Cross Station. 

My 11-year-old daughter was in tears after they kicked us off the second train because it wasn’t departing.

While we waited, she got to spend a few extra hours on Platform 5, not far from Platform 9 3/4 where Harry Potter and his classmates catch the Hogwarts Express.

Pretty cool for someone who’s read each book 10 times.

Eventually, they fixed the problem, and we arrived only a few hours late.

But what seemed like a terrible situation at the time has become one of her go-to stories when people ask her about the trip.

If my kids remember anything from this trip, it’s to enjoy the journey as much as the destination.

I Should Have Known

Travel was my original motivation for pursuing early retirement, which is why I began saving and investing so aggressively decades ago.

But over time, the stronger motivation to retire early became escaping an unfulfilling career.

That was an unhealthy outlook.

I should have known better, as I understood “the journey” during my early years of traveling.

It took years of building an online business to realize that enjoying work — with the flexibility and opportunities of entrepreneurship — was a far better pursuit for me than trying to escape it entirely.

I value having control over my time and daily decisions more than I value steady income or the trappings of professional success.

Having a business that I can run from anywhere in the world achieves what I initially sought when I set my early retirement goal — more travel, sooner.

The family part is a bonus.

Success and Control

When I finally left my career in late 2022 to become a full-time online content creator, I gave up on the idea of early retirement. 

Some newsletter subscribers unsubscribed because I was no longer the guy who didn’t like his job and was investing for an escape route. 

That persona resonated.

In a way, I stopped pursuing investment dividends in favor of lifestyle dividends. 

I’d always admired people who worked in careers they truly enjoyed, but never thought it could be me until about five years ago. 

I see friends, colleagues, and acquaintances in successful and fulfilling careers.

But with that success sometimes comes long hours, club memberships, private school tuition, demoralizing commutes, vacation home mortgages, and two $1,000+ car payments.

To them and anyone paying attention, it’s success.

But from my perspective, it’s a sort of confinement with no exit plan.

Perhaps if I had achieved two or three times my peak career salary when I was working, I’d have seen things differently. 

High earners are willing to sacrifice certain lifestyle choices to achieve career success and the prestige or admiration that comes with it. 

But success and lifestyle inflation can lead to a loss of control over their time.

For some, that trade-off is fine.

For others, they find my blog and write me emails. 

Yet none of this is black and white. Everyone falls on a spectrum, balancing financial success with control over their time and lifestyle.

When I left my job, I chose control over career success.

I maintain that control today and consider my lifestyle dividends a better indicator of success than a stable salary.

Ultimately, the dividends I care most about aren’t deposited in my brokerage account — they show up in my calendar, autonomy, and in the memories I make with my family.

 

 

Craig Stephens

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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