Early Retirement Experiment

dealing with the unknowns

We went into this Gap year with more questions than answers. Some people enter early retirement full of confidence in their carefully laid plans. They have no doubts, just “mountaintop shouting declarations” of what this next season will bring. Not us. We had questions, doubts, and unknowns. We went into our year off with an open mind and a list of questions; hoping to find some answers.

The questions weren’t even, “We think it will go this way, but know it might not.” Nope. More like “This is a big question, hopefully we can find the answer by the end of this.” Then there were other answers we learned. Ones not even on our radar to ask. “How will I feel not investing this year?” That question didn’t even make the list! But I quickly learned the answer. “I don’t like this AT ALL!”

It’s ok to have questions.

We ran the numbers, and then ran them 100 more times. But I wasn’t sure….about of a lot of things. I had a list of questions. And a pile of doubts. There are things that a spreadsheet won’t answer for you. A pile of great nonfiction books can’t answer for you. I can’t answer for you.

If you are thinking about retiring early. If you want to take a career break. If you want to change careers. If you want to start a business.  If you want to travel the world.

And I am sorry to tell you this but…

You won’t know until you try.

 If you never try, you will always wonder.

I think wondering is worse than a little bit of failure.


Seth Godin says, “You win by trying. And failing. Test, try, fail, measure, evolve, repeat, persist,…” We research, plan, and experiment. Maybe we get it exactly right. But maybe we find answers to questions we didn’t even think to ask.

According to writer Joseph Epstein, “81 percent of Americans feel that they have a book in them — and should write it.” That is about 200 million people just in the US. Google estimates only 130 million books have been published throughout human history. Clearly, we have a gap between desire and action.

I don’t know if you will enjoy writing a book. I don’t know if you will be able to finish. I don’t know if it will be any good. I have no idea if anyone would ever buy it. Maybe you have some doubts about that too. You won’t know until you try.

We might say it’s because we don’t have the time to write a book. But if you write 500 words an hour, for an hour a day, it will take 6 months to finish 80,000 words. So is it the time? An hour a day for 6 months? I can create a spreadsheet of the schedule for you. But I don’t think the spreadsheet is the real issue. Maybe it’s the questions and doubts that stop us from starting and trying. The questions can stop us from even preparing to do something big.

Can you create a great side business? Will you miss working after a few years of early retirement?  Will you find travel lonely, stressful or repetitive. Until we start, we won’t find out.

If you feel bursting with confidence about your plans, I am so happy for you. You know how everything will fall into place and all the details are nailed down. Sometimes, I become more hesitant by the confidence of others. Some people really seem to have their crap together. They have this 100 step plan for life, and everything is rolling along smooth as silk.

Don’t worry, that isn’t me. I had a list of questions and unknowns. In part two I will look at the laundry list of questions we had, and the answers we have figured out so far.

We planned the best we could.

We minimized the risk.

Then we jumped.


That long list of questions and doubts shouldn’t hold you back, but motivate you to start. How else will you know?

The results might be better than you ever imagined. Good things might flow into your life you never could have expected. But you won’t know. Until you try.

Two Steps to Start when You have Doubt

1. Really think about the absolute worst case scenario

Just let your mind go there. The case where basically everything goes wrong. When you walk to the very end of the worst situation; where does that leave you? I know it seems counter intuitive, but after you nail down the concern, you can find the solution. I have done this for every situation that creates some fear in my stomach.

Let’s say you take a year off to travel with your family. Maybe this is your worst case scenario:  “My spouse leaves me because I am a horrible grump when I travel. My kids die of cancer because we went to Japan and ate radioactive fish. Our house was burned down by our renters. Our homeowner insurance lapsed but I didn’t realize it because I couldn’t find an internet connection. My old employer tells every employer in our industry to never hire me because they were so mad I took a year off. I end up living in a cardboard box alone and die of leprosy I picked up in India.”  That is a little silly, but truly look at what the worst situation you might find yourself in.  Then figure out ways to minimize those risks. We can create a work around plan for those concerns.  Minimize your risk. Develop a backup plan. Honestly, those things I help you figure out!

2. Deal with Feelings of Failure

Here is the real issue that freezes us. The one that will create a non-start. The one I don’t have a great solution for.

What if I feel like a failure? What if others see me as a failure?

Our spreadsheets will help us with the numbers. We can plan for other possible situations. We can build a buffer into our budget. But it’s hard to be ok with feelings of failure. Feelings of failure are a very uncomfortable emotion. I don’t have any great advice, but here is what I tell myself.

“This is one of my biggest, most important dreams. For this goal, I will risk an uncomfortable feeling.”

That works about ½ the time. =) After the 4th attempt….

The things we try are rarely a 1 or 10. Dismal failure or Smashing success. Most of the things we try will fall on the continuum. 2-9, 3-7. We have to risk a few 3’s to get a few 8’s. At least 100 times in my life I have stepped out and tried something new. Only for 2 of those I felt 100% confident. The rest I went with a few questions, doubts and fear in my stomach. Yup, there were a few dismal failures, and a couple 2’s and 3’s on the success scale. But a whole heaping pile of good stuff as well. Amazing things I didn’t even seen coming. At 33 years old, I feel like the richness, abundance and goodness in my life is tough to measure. So I don’t mind those failures so much, because they helped bring us to this place.


And one more Seth Godin quote, “If it scares you, it might be a good thing to try.”

We didn’t start this year off having all the answers. We are learning as we go. We are trying things. Not because I am 100% sure they will go perfectly, but because I want to find out. We created a low risk environment. And we are experimenting. Full of questions and some doubts. It’s ok if some things don’t work like I thought they might.  A few things might go better than I imagined, and catch us by surprise. I’ll only figure that out by trying.

We don’t start because we have all the answers.

 We start because we have things we want to learn.



This will be part of a 4 part series recapping the all the questions we had, how the numbers look and what is next for us.

Which one is harder for you? The numbers or the unknowns? How do you find some tolerance for feelings of failure. Is there something you want to try or start laying some ground work for, but have been held back because there are questions about how it would all work?

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17 thoughts on “Early Retirement Experiment

  1. A 4 Part Series!! Yay, can’t wait. Awesome topic, and relevant to all of us! I love your quote: You won’t know until you try.

    Sometimes, we just have to plan as well as possible, then make the leap of of faith.

    I look forward to reading about your leap, and what you’re learning.

    • We went into this year with really open minds and a notepad to glean as much insight as we could. There are so many things you just can’t know until you start. So instead of pretending to know it all to give ourselves confidence, we framed it as a great experiment and fact finding mission. The only way you can fail on a fact finding mission is if you don’t learn anything! But we brought the notepad, so we are safe. =)

  2. For me, as I plan for a year off, I’ve found that mitigating the short term risk on the numbers is easy enough. Will it cause other long term risks? Potentially, but I don’t think so. It’s the unknowns that are scary as all hell.

    But as you mentioned, sometimes you just have to fight the fear, risk the possibility of failure, and go for it. I can’t wait to write my version of this post after my year off. 😀

    • I look forward to reading it! When I read about how people are 100% sure that everything is going to be amazing, I have more doubt instead of more confidence. Because I don’t feel like that. I have questions. I have concerns. So I wonder if it’s not for me. I was hoping this post would set the stage for those with a few questions. That have a bit of fear in their stomach. We didn’t have all the answers, and it has still be amazing. Better than I even thought. Maybe my honesty about the unknowns will give others more confidence. =)

  3. Great post! It’s that fear of the unknown that really gets all of us sometimes. We like predictability, we like knowing that everything will be just fine. But, in reality, there is always risk, no matter what.

  4. As we think about taking a year (or two) off we sometimes get paralysis from analysis. The numbers seem pretty good on the financial side according to the spreadsheets, but the what if scenarios can really generate a lot of doubt. We can fund the time off, but our biggest fears revolve around what happens on the other end of what we hope will be a great life-changing experience. Can we get decent jobs again? What about health care if we go for a while without working? Can we still help kids with college expenses? I think contemplating the worst-case scenario is a good way to put these doubts into perspective. It will ultimately come down to just taking that leap of faith. If it’s something we want badly enough, we will make it work.

    Definitely looking forward to the rest of your 4 part series on your experience.

    • Man, thanks Mike for sharing this! When Mr. Mt proofed this he was like, “You have done that worst-case scenario stuff so much, and it’s really helped. You need to do a whole post about that. Add it to your list!” But until then, it really does help. If you can very specifically name the concerns you have, you can think of solutions. Even crazy things like, “What if my child develops a brain tumor.” Then you can spend an hour or two looking into the options of health care sharing ministries (you don’t always have to have a religious affiliation) and programs at Children’s Hospitals and organizations like Ronald McDonald’s houses and realize that you have a possible solution. And maybe even a better solution if you aren’t working, because you would have the time and flexibility to move close to the best hospital and be available during treatments. It’s been really helpful for us.

  5. The surest way to fail is to never try. Yet it’s so common psychologically that we avoid starting something for this very reason. Failure instead should be a learning opportunity and if you plan enough you can just use that failure to guide your next opportunity.

    • When I am really nervous about a move, I label it as a “test” or an “experiment.” Actually failing isn’t so bad. A bit of wasted time, maybe some wasted money. It’s the feeling of failure that is hard to bear. I try to keep that in mind. The outcome I fear the most is that unpleasant feeling. Huge reward vs. unpleasant feeling. And a deep breath. =)

  6. Hey, Ms. M. Wonderful post. Mrs. G and I are big proponents of preparing for the “worst case scenario.” When we left New York for North Carolina, we arranged our North Carolina expenses to be so low we could survive on minimum-wage jobs. But fortunately for us, the worst case scenario didn’t materialize. Mrs. G kept her New York job and salary (thank you telecommuting), and I got a job that paid 2/3 of what I was making in New York. The key is to prepare as best you can and then go for it. It’s scary, for sure. But most times, our imagined nightmares never come to fruition. As you so eloquently put it, “[you] don’t start because [you] have all the answers. [You] start because [you] have things [you] want to learn.” Love the way your mind works, Ms. M.

    • We had some friends visiting right after we wrapped up our last rental purchase. They mentioned how we always take so many big risks, and that they just couldn’t do that. I laughed because I am actually very risk adverse. We carefully plan everything to minimize risk when possible. Even that rental purchase. The numbers were so good, that it would have been almost impossible to not make money. The “risk” was if we would make at little bit of money vs a lot of money. I think it’s easy to write things off as risky until you actually dig into the numbers and think about the worst case scenario. Your guys relation is such a good example. Minimize risk, create a plan, then try it out. =) You can always change your mind and move to Montana later. 😉

  7. Ooo, I love a series! I’m looking forward to learning about how you and Mr Mt decided the gap year was right for you guys.

    The “what’s the worst thing that can happen” reminds me of our honeymoon. We had a 12 day trip to Portugal booked six months after our wedding. The night before we left, we couldn’t find my husband’s passport to save our life….

    We ended up cancelling our flights and doing a big road trip from MN – UT – CA – Vegas – Denver – Iowa and back home instead. We got to see friends at each stop along the way, drive down the Pacific Coast Highway, and see my Grandpa for the last time before his memory started to deteriorate. It was SUCH a fun trip and I cherish the day we spent with my Grandpa that we weren’t expecting to have. At the time, losing a passport and cancelling the trip really felt like the worst case scenario, but it ended up being such a blessing! And a REALLY great story 😉

    Obviously the worst case doesn’t always turn out wonderfully, but I remind myself of the outcome sometimes when I’m stressing about the “what ifs” of a scenario.

    • That is a great story! I can’t imagine the panic trying to search for that passport. That would make me want to throw up. :/ But it’s a great example of how things might not go at all how we plan, but still end up being really good. Even bad situations can open the door for new good options.

  8. Great way of making us really think about the worst-case scenarios – and how likely it is that they would happen. I am going to make a big jump and take some risks in the future, but I feel responsible to my family first. As the breadwinner, I have to bring home the money we need to fix our finances before starting off on a new adventure. It’s always tough balancing that drive to be impulsive and follow your dreams, with the adulting responsibilities.

    • The spreadsheet numbers definitely need to work first. I’m not in the “jump and then figure out the numbers” group. But even after the numbers seem good, there are a lot of questions you might not have answers to. I think you are doing an awesome job Harmony. =) Bit by bit you guys are getting there.

  9. Excellent posts. With hindsight, you bring to words, good words, the process I went through when I started to trade options and when I left my corporate job for a startup.

    I hope these words inspire me now to ask a month of parental leave.

    • I think any big change causes some questions with out answers and a little fear in the stomach. I’m excited about your month of leave. I hope that conversation goes well. =)