The First Steps Toward Planning a Nontraditional Retirement
Montrose County Fall 2026. Photo by Wendy Stieg
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Say the word “retirement,” and most people cringe. At least I do. I still feel like I am 25 and filled with joy, with young ideas, but maybe a bit more wisdom. I also have a few more pains, but living a busy, active life will do that to you. I wouldn’t change a thing. I think the word “retirement” says to a lot of people that you just roll over and stop living. To that I say, “Says who?” I did not live my life conventionally, ever, and I am not about to start now.
In What's Your Plan for Life Beyond Work?, I explored the bigger questions about retirement, purpose and creating a life beyond traditional work. Now it's time to look at the numbers behind those dreams.
First, Identify What Matters in Retirement
Laughing while wearing Melanzana, at the westernmost point of Europe, in Portugal. Photo by Miguel Rodrigues.
For years, I've fantasized about building a life that would allow us to travel, explore new places and work for ourselves. Now we're finally putting those ideas together. We're combining bucket-list adventures with scouting trips to places we might eventually call home, and using those experiences to create stories for my blog and content for Paul's sports podcast. Over the next three years, we're planning trips around Europe's three major cycling races: La Vuelta, the Tour de France and the Giro d'Italia. Paul just added to the timeline: The 2030 FIFA World Cup is scheduled to be in Spain, Portugal, and MOROCCO! We are definitely adding that to the list!
Our loose plan is part travel, part retirement research, and part building a business around the things we already love. Will it all work out exactly as planned? Probably not. If there's one thing Paul and I are good at, it's changing the plan! But for the first time, those dreams have a timeline and a purpose beyond simply wishing we could make them happen. We are starting to see evidence that this plan is working. So we will keep going until our plan comes to fruition.
I am writing a loose series around these ideas. If you like the sound of figuring out ways to incorporate your passions, living the life you dreamed of, and finding ways to stay healthy, then please keep following us! Today’s assignment: Take a hard look at your retirement picture and identify the income gap. Maybe you are a better planner than we are and don’t need that piece. But we are planning on holding on to our dreams as we keep on living.
Exploring places you might eventually call home? Airalo offers travel eSIMs that can help you stay connected while navigating unfamiliar destinations, researching neighborhoods and keeping your plans flexible.
Figuring Out Retirement Finances Matters. Start by Looking at What You DO Have
Snapshot of a snapshot planner.
I would start with Social Security. Colorado has PERA if you had a state-level government job, so you need to look at which benefits you qualify for and how they work together. You most likely have other retirement investments. You may have other savings accounts and so forth. Find all of those and see if you can get an idea of what monthly money you have.
Where will you live? If you have a home you own, is it paid off, or will it be shortly? If not, will you be selling it? You have to start gathering all of this information. Also, what debt do you have? Really research what age you think you want to retire. Paul wants to retire at 62½, but I don’t think that can happen. I wish we could get the maximum money possible, but waiting until 67 is maybe not great either. I like using age 65 as my retirement age, given that I will hopefully qualify for Medicare and have time in the States with health care coverage.
If living abroad is part of your retirement plan, managing money across borders is another consideration. Wise offers international money transfers and currency conversion, making it worth exploring as you begin researching the financial side of living in another country.
Our plans may be different than yours. We know we will be looking at either selling or finding someone to manage our property for rentals, either short- or medium-term. That would give us income, but selling would give us cash. Over the next few years, I will be researching both. I use that as an example because it is an area that can generate money for us. You have to look at your situation and figure out other sources of income.
Free Retirement Financial Starter Planner
Ready to put some numbers to your retirement plans? Download this free, printable organizer to help you gather your income sources, savings, expenses, and other financial information. It's a starting point for identifying potential gaps and thinking about your next steps.
Download Your Free Retirement Financial Starter Planner (PDF)
Start to Brainstorm Ideas: What Are You Good At?
Writing while camping. Wendy and the Blog. Photo by Paul Lampe.
About four years ago, I started thinking about this. What am I good at? Well, I know that I have always loved writing. I also had a strong fear keeping me from being public about it. Well, sort of. I did enjoy writing posts, which seems silly and trite, but it did show me that I could capture people’s minds briefly and ask them to consider things. I was good at that as a teacher, too. I loved having great discussions with kids and just watching their minds take off. I also knew I was good at finding ways to engage people.
It turns out that those are very important if you want to be a writer. I also realized I didn’t want to BE a writer. I have always been a writer. I just wanted to find ways to break out of the cage I had built myself. That meant I had to stop worrying about what people might think about me and worry more about how I wanted to capture imaginations and ask people to come along for the ride with me.
Over two years, I have built a blog that has over 8,000 viewers and 1,300 monthly views. I realize there are blogs with a lot more people in those categories, but all of those bloggers started exactly where I did: JUST start. You will get better, and you will learn a lot.
What are you good at? I promise you are good at a lot of things! Also, what do you love to do? I have already done things that I needed to do, but now I am focusing on what I love to do: write, travel, get out into nature, spend time with friends and family, and spend time in a present, meaningful life.
I also want freedom, maybe most of all. Freedom to me means geographic, physical, spiritual and emotional freedom. That means traveling and getting to use my time how I want to. Being able to articulate that also matters. Next question: What would you do if you could do anything?
I wrote about taking those first steps in Building Best of Both Worlds, when I began learning that I didn't need to have everything figured out before starting.
In Closing
Wendy in Diamondhead Beach Park and Outrigger canoes outside of Waikiki circa 1985.
Don’t be afraid. Step out of your comfort zone. Leave the Shire, Frodo. You might just find that there are things you shelved many years ago. I don’t remember why, but I remember that I somehow got talked out of journalism. It was my plan if I had stayed in Colorado. But wanderlust got a hold of me instead. So I stuffed journalism to the side and moved to Hawaii. By the time I had taken a year off and had gotten into Chaminade University of Honolulu, I had lost the drive to write, even though I ended up writing to some degree the entire time I was at Chaminade.
Well, now I am writing again. I have been asked to use some of my articles in Medium publications, and I just finished writing an article on skijoring for Spoke + Blossom, a Western Slope magazine. I will link it in my blog once it is published online. That is exciting and promising. I wouldn’t be here if I hadn’t ventured out and trusted myself. You can do that too! Was there something you gave up? Maybe now is the time to think about doing it, and maybe, just maybe, it can also be part of your plan to take you through the next chapter of your life!
As I close this article, a final thought occurs to me: I did struggle with the transition between teaching and figuring out what my next chapter would be. I strongly resisted the lack of work. That felt almost like the Universe was sticking it to me. But the truth is, without those two years, I wouldn’t have started a blog. I wouldn’t have pushed myself to learn Portuguese, and I wouldn’t have thought about living life as I do now. Those two years without a job were a gift, after all. I now have a job that fits better than I expected, and my writing continues. If you are in a transition right now, remember that it is just a brief course correction, not an ultimate destination.
