Risk and Reward: Overcoming the Doubt Can Transform Your Life

Risk and Reward: Overcoming the Doubt Can Transform Your Life

When I was younger, weighing the risk and reward in a decision was a lot easier. In your youth, you’ve got time on your side and most of the chances you take aren’t going to make or break you.

If you’re in your younger years, remember that. Don’t be afraid to take calculated risks that can change your life for the better.

As time marches on though, the choice between risk and reward can sometimes be a lot tougher. When you’ve got more on the line to possibly lose (a steady paycheck to be able to take care of your family, a community of people around you’ve known for a lot of your life, etc.), your mind tends to fight for you to take the more certain road.

That’s the way life usually goes.

But sometimes you need to push aside those doubts about taking the path less traveled. That could mean the difference between a mediocre life and a mind-blowing one.

When I was younger…

In my twenties, risk and reward weren’t something I thought about much. I worked hard at every job I was employed at and enjoyed my time at every job (except for one grueling manual labor job).

Back in 1995, I got a job at Walmart working part-time. I was going to college and needed some income to, well, to be able to eat anything more than Ramen noodles (though I’ve got no problems with that cheap tasty meal!).

Just like my other jobs, I did my job and did it well while still having fun there. I even got my 30 seconds of fame with a regional Walmart commercial…

But if you do your job well like you’re supposed to, have fun, and don’t complain, you tend to move up. I went from a part-time guy in the jewelry department (that’s all that was open when I started there) to full-time to the Menswear department manager and then to the Sporting Goods department manager.

I didn’t care about the changes – I enjoyed it and making a little more money was a bonus.

After that, they gave me an opportunity to become an assistant store manager. I would need to move to another store though that was about a 45-minute drive away.

Whoa, whoa, whoa… that’s a big change, a lot more pressure, more hours, and a much longer drive.

Now, I could have bailed and stuck with what I knew was working. But it’s all about risk and reward… with the bigger paycheck being part of the reward. So I did it.

And even with those changes I mentioned, I still enjoyed it. I was still in college part-time but now making a good salary. Life was good even though I’ll concede that I was drained from everything going on for sure. Regardless, I eventually moved to another Walmart that was closer to home.

At this point, it was now becoming a career.

Fade over to the college backdrop where I started as an art major. After a couple of years there, I decided that although I enjoyed art and was pretty good at it, I didn’t want to do this for a living. Eventually, I randomly took an “Intro to Computers” class (this was before computers were really prevalent) and I loved it – so much so, that I changed my major and decided that was my new career path.

Come back to Walmart and I remember one of the other managers rattling off some statistic about how someone who stays in retail for x number of years tends to make that their lifelong career. I was close to whatever that number of years was and it actually freaked me out.

So I went home, considered the risk and reward, and made the decision to leave my job at Walmart. At that time, I was making good money for a kid my age, I was doing well and could have pivoted to multiple directions in retail from there, and I had no other job lined up.

It didn’t matter. I was sure I could make it work. As a footnote, remember, that I was young, not married, no kids, and still living at home… the youth equation tips the risk and reward scale again!

I turned in my resignation at Walmart, worked on a resume, and went door-to-door in a few industrial parkways wearing a suit and peddling my resume. Eventually, I struck a win and found a company that trained me as a Systems Engineer where I eventually became the manager.

I likely made more money over the years there than I would have if I had stayed at Walmart, worked a lot fewer hours, and got to do something I had a passion for. I stayed there for almost 20 years until it wasn’t as fun anymore and that’s when I retired.

Without taking that risk, I wouldn’t be where I am today.

Taking risk and reward to a bigger level

Those are a few small examples of taking into account risk and reward. But they’re also nothing too out of the ordinary – changing majors and careers isn’t that uncommon.

But what about doing something a little more unorthodox?

With the exception of some of those changes in my twenties, I didn’t fully understand the opportunities that risk and reward could play in your life. It just wasn’t something that I had even thought much about.

As the years went on though, I started to get it a little more. I began making some changes that were maybe a little more conventional at first but still a new world for me. A perfect example of this was trying new ventures on the side that had a small risk but the reward had the potential to be worth it. Some of these were:

  • Writing a technical book
  • Buying a rental house
  • Writing another book
  • Buying another property… a duplex
  • Starting the Route to Retire blog and brand

None of these made us rich, but as they built on each other, I learned more to help with the next endeavor, which made it worthwhile. For instance, I was such a newb when I bought my first rental house that I’m lucky we got out of it in the long run probably making an ever-so-slight profit. But buying the duplex a decade later was a success story by leveraging what I learned. We made excellent money every month on that and then sold near the market peak for twice what we paid for it.

Risk and reward.

The big epiphany in life though was the realization that early retirement was a thing (shout out to Joe Udo from Retire by 40 as always!!). This was something that drew me in and I learned every aspect I could.

Eventually, I realized that this had a lower risk (if executed properly) and a huge reward – owning my time and the freedom to choose how to use it. I could always go back to work if it didn’t work out, but that gave me the reward of being able to able to be around my daughter more as she grows up – something you can’t get back later in life.

Despite the naysayers, after nearly 5 years of early retirement, I’d say things are going well. That led to other changes that were bigger and more unorthodox as well. A few of the uncommon changes we’ve made:

  • FIRE (Financial Independence / Retire Early) – As mentioned, this was a lower risk with a higher reward.
  • Moving to Panama – I wish we’d have stayed there longer but this 3-year experience was amazing and helped re-shape all of our lives!
  • Homeschooling our daughter – This went along with the Panama move with the intention of possibly enrolling her in an international school later. But it’s been great for Faith and also for us so we’re still doing it now (though I don’t think this would work for all kids).
  • 30-40 day road trips – After realizing that time is on our side, we took a massive road trip in 2020 and then another in 2022. Taking vacations that are long like this isn’t the norm and can be expensive, but it’s also eye-opening to be able to see beautiful parts of the country we probably wouldn’t get to see otherwise. Plus, it’s a lot of together time as a family!

None of these are things that the majority of folks out there are doing – and we received a fair amount of criticism and doubt from strangers on the internet, friends, and family (especially on retiring early and moving to Panama). It would have been easy to let that doubt invade our own thoughts and bail on the whole thing.

That would have been a mistake. Ignoring the noise and seeing the value in the road less traveled proved to be monumental and epic in our lives.

Our latest endeavor and the doubt that keeps creeping in

By the time you read this, we’ll have officially moved into our 2022 Jayco Jay Flight SLX 7 RV travel trailer. She’s not huge but she’s a beauty!

Risk and Reward: Overcoming the Doubt Can Transform Your Life - 2022 Jayco Jay Flight SLX 7 184BS
New pictures to come now that we’re on the road!

This seems easy enough, right?

But here’s the thing – we just moved out of our apartment, put what we owned in storage, and we’re taking our life on the road for 9 months or so.

This is insane. We’re in our 40s with a 13-year-old daughter. Who does this? And what the hell do we know about RV’ing?

Finding a legitimate statistic is tough, but the RV Industry Association (RVIA) released a study showing that 40% of RV owners are between the ages of 18-54. Now, I would bet that the far majority of those owners are not full-time RV’ers. I would also guess that the full-timers in my age bracket are a relatively equal portion of what’s left.

When all’s said and done, I’m guessing that what we’re about to do is in the single digits and isn’t very common for folks our age… especially with a kid.

And that’s absolutely OK with me.

After pulling off early retirement despite the pundits as well as living in Panama for a few years despite the critics, I’ve learned that taking the path less traveled yields an amazing world that most can only dream about.

So there’s that. But to answer the question about what the hell we know about RV’ing… not much.

And apparently, it’s a lot less than I thought. Lisa and I have dug into everything full steam ahead since this whole idea was born this past spring and we’ve learned a lot. I can also tell you that I now know that this trip is going to be a lot pricier than I had first imagined. The idea of getting close to breaking even on our entire living expenses once we sell the truck and trailer next year is most likely a fairytale I had envisioned.

I now realize a lot of what to expect (and there’s a lot I don’t know yet). This is going to be a costly adventure and that’s when some of the doubts start to creep into my head. Is this a bad idea?

Risk and reward.

Here’s what I know – this is going to probably be one of the last long-term memorable things we do together as a family of three. Faith’s both excited but also a little hesitant. At 13, she’s giving up time with friends and her time horseback riding (her extracurricular activity) and volunteering a the equestrian center. At the same time, she knows this will be a really awesome trip (her words).

I’m sure it’ll be worth the cost and I know we’ll have a great time, but there’s always that lingering doubt.

We could have just stayed in our apartment, lived a “normal” life, and done a few vacations throughout the year instead. That would have been fine, right?

Probably. But when you weigh the risk and reward, I think this opportunity to take our time and visit so many incredible places while boondocking beats the staying-the-course option any day!

Hopefully, by the time you’re reading this, we’ll already be settled into a little bit of a rhythm as we do our test run at a local campground. And maybe tonight, we’ll be sitting around a fire and talking about all the cool places we want to go.

Life is good. Take a few chances and push your life to the next level. Risk and reward – if it’s a calculated risk, the reward could change your life in ways you can’t even imagine!

If you enjoyed this post, hop on the mailing list. I’ll even send you some spreadsheet goodies I’ve created that I think you’ll find useful as a simple thank you…

On another note, I finally put out the YouTube video I was working on for a long time… Installing an RV Air Head Composting Toilet… with Plumbed Urine Diversion. It was a lot of effort to make but I’m learning that I still need some work to make a video like this more exciting. Regardless, I think it’ll be pretty useful for other folks like me who want to install a composting toilet but divert the urine to their gray/black tanks (another unique change!).

I plan on putting together some fun videos during our big adventure so head over to the Route to Retire YouTube channel and subscribe now so you don’t miss anything.

Have an awesome week, friends!

Plan well, take action, and live your best life!

Thanks for reading!!

— Jim

You know you wanna share this!!

8 thoughts on “Risk and Reward: Overcoming the Doubt Can Transform Your Life”

  1. Great insight Jim, love the old Walmart vid! Yes, you articulated Risk vs Reward very well. I have a long-time friend who I tried to convince back in 2005 when I bought my first rental property, come to me just the other day and tell me he wanted to look at buying a rental. His reasoning is, he doesn’t really know how secure his job is any more. Thats a scary place, and now he’s 53 has 2 kids, a job he might not have tomorrow, and no equity in property that he could have bought 18 years ago.
    Moral of the story….. is his risk higher now or was it 18 years ago?

  2. Risk and reward is certainly something I consider with real estate, but now it seems there is more risk and little reward. It seems the more your net worth goes up, you should be comfortable taking more risk having a greater cushion, but you are more risk averse because you’re scared of losing what you built up. Thanks for the article!

  3. That’s pretty amazing. It’s great that your wife and daughter are up for some adventures. I give them a lot of credit. 🙂 My family is much more conservative. I’m also getting more risk-averse as I get older. My young adventurous days are behind me. We’ll travel more when our son goes off to college, but it’ll probably be pretty cushy.
    Thanks for the mention!

    1. Nothing wrong with cushy! I would bet after we’re all done with this, a lot of are traveling might start to shift to some more traditional vacationing as well. That said, some of these adventures have been unquestionably life-changing!

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