Last year at age of 70 years young, I did this trip:
Bike Tour near Lake Ontario and part of Erie Canal - June 2024

Plus two backpacking trips and a canoe trip in northern Minnesota.

I am a bit slower than I used to be, happy to do shorter days than before, and a bit less interested in high levels of exertion. When I was backpacking in the Rockies in my 20s, I discovered I have bad knees, so I have to limit over-stressing them. I don't enjoy these trips as much as I used to, but if you stop doing physical activity, you might find you can't restart it again. I am still happy to do tent camping, motel rooms are too confining and boring.

This past May, a medical issue popped up for me. Not being life threatening means long waits for treatment. Long bike rides are still doable, but long walks are not. I planned to be backpacking right now, but canceled that trip. Starting to think about what I will do next year when I should be fully recovered.

The thread title made me realize that I almost didn’t make it through New Year’s Eve of 2022 to see the next year.

In addition the tours you do later might be different than those earlier and even the places you travel could be different. As mentioned, I am fortunate to have taken multi-month trips at ages 29, 34, 38, 44, 50, 53 and 60. The sort of trip I took at age 29 (six week intense ride from Astoria to Portland ME averaging 95 miles/day including rest days) were different than the trips I took at double that age. Both are fine in their own ways but I also feel fortunate to have had the earlier trips. Doing a ride around Australia now would be different than what I did at age 38 since I would have to break the larger gaps into more pieces.

^^^IKR^^*

I did 6,000 miles during my first tour. I was 34. Did two seven-week tours the following year, including Seattle to Cortez, CO. While I was in MT in June I thought about the long days I pulled as a ute. Even days I pulled off in the 2010s seem impossible now.

You were fortunate to have the available time away from work to do that. My first bike tour was when I was 55. My second bike tour was a few months after I retired.

That said, I did a lot of week long canoe trips and kayak trips during the working years, and before that did several backpacking trips during summers while in college. For me the bike touring came late.

You gotta either be a student or just quit your job. Both of these are easier when you are young.

Then later when you are more advanced in your career, you can transition to self-employment and get flexibility that way.

I see a lot of young people and retirees touring. Very few middle aged people.

That’s pretty much the way it was on my group cross country tour. There were 12 of us, excluding the leader. I and one other were in our 30s. One person was in their mid-50s. She was a teacher, so she had summers off. Three people had just finished higher education, and one was about to start her senior year of college. They were all in their 20s. The rest were 60 or older and retired,

I had been downsized in the wake of a corporate acquisition. Ended up taking exactly two years off and then got my old job back.

Yes, I do feel fortunate. Though having managed people for 30+ years in large companies it may be more accessible for some and it may also require some explicit career tradeoffs.

I've worked for exactly two employers since graduating from college so four of these long absences were personal leave of absence for 12, 10, 6 and 6 months in accordance with HR policies from the company.

How did I get those leaves? A few things to recognize:
1. A large company will have legally required leaves they need to support (e.g. maternity, military deployment, FMLA).
2. They may also have a leave policy for an unprotected leave as a personal leave of absence. Examples might be to have an employee do caretaking or perhaps an education on-site degree. So these come at discretion of the managers and there are no guarantees (of the company for a job or the employee returning). So it relies a lot on trust and relationships with managers ...
3. There may not be a huge cost to a large company to grant such a leave. They aren't paying you. They aren't guaranteeing a job. What they are doing is maintaining a tighter relationship to a good employee than going a quit/rehire approach.
4. So how did I have my managers approving such leaves? A few different techniques (a) I asked way early, often in context of career planning, e.g. "I'd like to keep growing this team but perhaps in two years take a chance to do something a bit different and along the way take a break for some extended bike travel (b) I had a lot of mutual respect with my bosses and made sure I got a lot done as a top performer (c) I didn't do this by making myself indispensable but instead the opposite including growing team members, doing transition plans etc. (d) while there were no job guarantees I also made sure I had up to date and current skills. I also reassured my bosses I had every intent of returning (e) I was willing to be flexible, e.g. I wasn't looking for my old job back, typically the opposite something similar but slightly different where I could contribute to the company in a new role and keep growing my skills in new areas. When I came back it was sometimes working with managers on the next role.
5. I also made some explicit career choices. 25 years ago I was leading a group of 40+ people. If my goal had been to lead larger and larger groups in a company, taking a year LOA to cycle Australia wouldn't have been the smartest move. But that wasn't my goal - and I was at least as happy going back and leading a smaller team elsewhere.
6. I lived below my means and was single. This meant I would be fine with no income for a year and also didn't have dependents affected by my choice to tour for a year.

So by asking years early, discussing in context of larger goals, getting a lot done when I was at work and making some choices on career progression - and being fortunate in the employers/bosses I had - I was also able to create a situation where I could work for 4-5 years, go on a long tour and then come back refreshed and energized into new roles but still with two employers.

So for example, my last six months leave in 2023 was requested in 2021 and was a chance to take a team I built, transition it to next phase with people I had grown and have me come back elsewhere in the group in a new role - all with support and collaboration with my manager.

Was I fortunate and lucky, yes. Am I the only one to ever be able to trade things off for a goal of longer bike trips or manage a career with such a side goal, probably not...

It was a restructuring that got me started with my pattern. In particular I had been fortunate to take a six week trip when later that fall our group was eliminated.

In light of that restructuring my immediate focus was on finding a job again (and found one in the same company but moving). However the other thoughts were (a) I am really fortunate to have done that trip since it would be hard now and (b) if the company can "restructure" I can too ...

So I made a personal goal to get another extended trip in "five years" and worked towards that goal including asking my manager way in advance and even worked out how we could use this as an opportunity to rotate to our sister organization in CA after my trip.

Three months after my second trip, the company again restructured and closed all the offices in MA. So if I had done nothing, I would have been affected - again a reminder that I sure was fortunate to have taken such a trip when I could...

I am sure that there are others out there that were as fortunate as you. I have had some great jobs and some very poor ones. Same with bosses. Life is an endless roll of the dice with many twists and turns.

My last boss told me that he was going to cancel my vacation because they were so busy. I decided that I could retire early and by staying frugal could live for several years off of my savings, so instead of him canceling my vacation I turned in my notice. That was 15 years ago and I have never regretted it.

Congrats.

"...instead of him canceling my vacation I turned in my notice." Very bold, yet smart move. I have made that move when a company I was with was headed where I didn't want to go.