Why Financial Success Often Depends on the Road Not Taken

Decisions, decisions. Like it or not, our lives are defined by them.

It’s no secret that a big part of our financial success is based upon the decisions we make in life.

Just ask any person who has jeopardized their financial future by, say, starting a family before securing a good job.

Fortunately, most of us will be lucky enough to be afforded with at least one or two challenging opportunities — and hopefully, lots more — over our lifetimes that we’ll choose to either accept or decline.

As a recent assignment for his latest Two Guys and Your Money podcast, my friend Joe Saul-Sehy challenged me to pinpoint an opportunity that I was presented with sometime during my lifetime and the resulting impacts of my decision.

Looking back, I immediately focused on a challenging opportunity I was given just a few short years into my nascent engineering career.

My boss had asked me to essentially take a four-month assignment in a North Carolina town almost 2500 miles from home, and support a small team working on a project I knew virtually nothing about. Being young, single and unencumbered by any real responsibilities at the time, I decided to accept the assignment, even though I was deathly afraid of the uncertainty before me.

Reflecting back in time, my initial assessment of the major impact of that fateful decision was rather ordinary: Upon returning home, my employer gave me a nice promotion and more responsibility.

But then I thought a little more.

It turns out, the more I thought about it, the more I realized that decision to go to North Carolina had a bigger impact on my life than I ever realized. In fact, the opportunity my employer presented to me was not unlike the fork in a yellow wood described in Robert Frost’s The Road Not Taken. It was a fateful decision that ultimately impacted other choices I ended up making in the future. Let me explain:

If I wouldn’t have taken that special assignment, I wouldn’t have received my big promotion.

And without the big promotion, I would have never got the raise that allowed me to buy a little house in Southern California for a ridiculous price at the top of the market.

If I didn’t buy my little over-priced house in Southern California at the top of the market, I wouldn’t have been stuck with an upside mortgage for seven excruciatingly long years.

Of course, if I wasn’t upside down on my mortgage, I could have eventually moved to a much better home in a much nicer city — but then I never would have met the Honeybee.

If I wouldn’t have met the Honeybee, I probably never would have had kids. Eventually, we had two: Matthew and Nina.

Then again, if Matthew and Nina weren’t born, I wouldn’t have had an insatiable desire to earn a little side income to help pay for all the added current and future expenses that naturally come with kids.

That insatiable desire for side income led me to begin writing a personal finance book, but I never finished it. That’s okay, though, because if I hadn’t failed to write that book, I most likely wouldn’t have decided to start this personal finance blog, which has provided me with a very rewarding pastime.

Now, I don’t mean to imply that my decision to temporarily pack up and move to North Carolina was the lynchpin decision of my life. I realize that my life’s way points have been determined by countless other decisions I’ve made since grade school.

Still, I’d be lying if I told you I’m not curious as to where I’d be today if I had chosen some of the other roads not taken during my lifetime. I’m only human, after all.

Even so, I can honestly say I have no regrets.

Photo Credit: Connie


  1. 5


    I have often tried new opportunities. When I was in the restaurant business, I had an opportunity to start a studio catering company. That is where catering trucks go out to movie shoots and feed the cast and production company. It can range from a few hundred people to thousands. Usually 3 meals a day for weeks or months. It is extremely lucrative and you have a contract. It was a great business and I never would have tried it if I were not already in the restaurant business.

    • 6

      Len Penzo says

      That sounds like a great adventure, Larry. And I don’t think I would bother trying to take that job on without some restaurant experience first. I’d like to see your autograph collection one day!

      • 7


        Hi Len,

        Sort of related to this post, perhaps you would write a post along the lines of what are the best businesses to start now that will do best during the reset. One can read articles and posts that recommend things like bicycle repair and farmer. I am thinking there are other more creative businesses, even internet based, that will do well. I am just not coming up with any specific ideas. Thank you, John R.

  2. 8

    Fran Rupley says

    The best opportunity of my life came as I was a secretary to engineers in the old days of computers; when an opening came up for a computer trainee, I was accepted and my whole family’s life changed. Night and weekend classes meant hubby and kids learned a lot of self-reliance! Resulting promotions and raises helped build up a good retirement, I was able eventually to telecommute from home full time, allowing us to move to a country property with hubby retired early and being the house husband!

  3. 10


    Funny. I told my kids this story:

    IF I wouldn’t have accepted the track scholarship at The Citadel I would have never run in college and gained enough resume experience to later become a coach. If I’d been a great runner, though, I wouldn’t have decided to make the trek back home to Michigan State after two years to complete my degree there. If I had been good enough to run in the Big 10 I wouldn’t have applied for the middle school coaching job in nearby Williamston where I met Cheryl. If I hadn’t met Cheryl we wouldn’t have gotten married, and if we hadn’t gotten married, we wouldn’t have had our twins.

    The point? My kids owe their lives to the fact that I’m a crappy runner.

    • 11

      Len Penzo says

      You don’t look like a runner. What made you think you were going to be a good runner? lol (Sorry, I like laughing at my own comments.)

      I joined the track team in 7th grade. I wanted to run the 100 yard dash. My track coach had other plans and decided I was a hurdler. So he made me train for all the hurdle events: 100, 220, and 440 yards. I hated the hurdles. Absolutely hated them. For obvious reasons. Anyway, on the first track meet, on every event I tripped over a hurdle and fell on my face. Obviously, I was NOT a hurdler. So I quit the team the next day.

      How’s that for inspiration? 😉

  4. 12


    I am very glad you went to North Carolina; otherwise I would have had hard time finding another blog to visit and read (and enjoy and find stimulating). My move across Europe had a major effect as well…:) I always think about the movie ‘Sliding doors’ when thinking about that.

    • 13

      Len Penzo says

      Thank you, Maria.

      I just looked up ‘Sliding Doors’ on the IMDb website — the premise looks really interesting, so I am going to add it to my Netflix queue.

    • 15

      Len Penzo says

      That’s true, Pauline. But there are so many branches along the way, the odds of that happening seem a bit remote, don’t you think? :-)

  5. 16


    I often think that if I hadn’t gone on a family vacation to Colorado when I was 15 or 16, I probably wouldn’t have wanted so badly to move to that state in order to go to college.

    And if I had chosen a different college (I applied to more than 10), I never would have met my boyfriend of 5 years, Will.

    And if I hadn’t met him, I probably would have never started investing in real estate, which was initially his idea. (And Will would have never moved to Atlanta, which was my idea).

    Funny how one tiny family vacation could have changed so much.

  6. 18

    Jared says

    This has been encouraging to me! Due to the economy, I feel trapped in the contract work merry go round. I’m right out of graduate school, and haven’t been able to establish my career yet.

    This helps.

  7. 19


    I wonder what would have happened if I never moved to Atlanta: I wrote a book, started a blog, attempted at a few other things that didn’t pan out, and now I’m working on putting a women’s financial conference in Atlanta fo June 2013.

    I have to say you can’t always plan out your life. Actually, maybe we shouldn’t plan everything, just some. I would imagine, like in my case, the bumps, potholes, and detours, are there to learn how to overcome them.

  8. 22

    Doug says

    For me, life has always been like a river. I feel and follow the draw of the current. However you can move out of the main current and at the sides you find eddies and back currents. Sometimes you find yourself going backward as the river goes forward. And once I finally regain the main current, I know that it will lead me to where I should be. Not to say that it ensures an easy ride. Oh no. You know how there are calm parts, and then there are the rapids. Well our river just threw us off a very high waterfall. The plunge was terrifying, huge, jagged, sharp rocks at the bottom. As we fell, an opening appeared and we fell through it. And on the other side we found our new home. Paid for in full. We now celebrate our first Christmas in our first home, you see, we have always been renters. Looking forward as far as I can see, the waters are calm and very inviting.
    Merry Christmas Everybody!!

Leave a Reply

Your email address will not be published. Required fields are marked *