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?

If you want to get my new pdf laying out the 6 steps to taking a year off, make sure you sign up for my newsletter and I will send that out to you for free.


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