How do I tell my boss I am bike touring for 3 months (and keep my job)?!

[BikeliciousBabe]

I told my boss and my customer I was going to ride across the country for three months (about 4-5 months in advance).  I think the certainty of my telling them helped cement the idea I would be gone for that long and make appropriate adjustments.  Their response to me was, "But you'll be coming back, won't you?"

My situation was such that I was prepared to find another job, if that had been the way the conversation ended up.  As it turned out, three months was enough for my customer's organization to go through another periodic "reorganization" (read: purge), and my job there disappeared when I returned.  Fortunately, I was able to find another slot in the new "organization," so except for a few weeks where my leave ran out, I never had to pay for my benefits.

Oh yeah?  Well...After three years at a job I volunteered to be downsized, got a decent severance package and other goodies while the merger was being approved, took two years off from the working world to tour 10,000 miles and otherwise enjoy life, then got my old job back and have been at it for nearly another 22 years.  So there!   

[ray b]

Sounds like you are good at your job.

In that context, a leave of absence or modified job for 2-3 months shouldn't be an issue - especially if you make yourself available for meetings and questions.

We've all met people who are on the road and still working from their computers.

[staehpj1]

There are always at least two possibilities.  They figure out that you do way more than they imagined and they really miss you.  Or they figure out how little you actually do that is actually of any value.

I think in my case the trip on the TA actually helped my career.  They seemed really glad to have me back and treated me better after when it came to salary actions and so on.  I figured there was some risk it could be career suicide though.

[ray b]

As I prepare to get ready for another leave of absence, I returned to this thread.

Strikes me, If you're looking for success stories, there's plenty of us who've been down this road.

I applied (asked) for my leave of absence 6 months in advance (Bikeliciously) and came back to find not only that I was missed - good for my career (Staehpj1) - but also, that my co-workers were more confident in themselves and functioned better after they realized they could handle the extra responsibilities.

It's this latter phenomenon that you might want to play up if by "key position" you imply leadership. Always good for the troops to learn the jobs of others and to be able to function fairly well with the temporary loss of "key" personnel. You might suggest that your relatively brief absence might improve the stability of the business.

[David W Pratt]

I concur with BB.  Call it a sabbatical maybe, implying that you will be returning.
Having incriminating photos of the boss might not hurt either.
Good Luck!

[j1of1]

Do the TRANSAM or equivalent in "chunks" or "sections" vs doing it all at once.   I've had many friends and have hosted (WarmShowers) many cyclists - and most of them that had jobs - that are doing it in pieces and loving it.  My own personal experience is that I'm going across the USA by completing one or two sections each year.   Last year (2022) I cycled from Washington DC to Dayton OH (Section 1, 12 days) via the C&O, GAP, and Eastern Express to complete Section 1 then in the Fall I cycled from Kansas City back to Dayton (Section 2, 15 days).  In 2023 I plan on bicycling Section 2 which is from Kansas City to Pueblo Colorado.  I plan to complete Sections 3 (Pueblo Co to Missoula MT) and Section 4 (Missoula to Astoria OR) in 2024 and 2025, respectively.

The good thing about doing sections vs all at once is that each year you'll have something to brag about to your co-workers as well as having something to look forward to each year.  Whether you take my advice or do it all at once you'll have one of the best experiences of your life.

[ray b]

Do the TRANSAM or equivalent in "chunks" or "sections" vs doing it all at once.   

The good thing about doing sections vs all at once is that each year you'll have something to brag about to your co-workers as well as having something to look forward to each year.  Whether you take my advice or do it all at once you'll have one of the best experiences of your life.

A great solution for those who cannot realistically take the big chunk of time - we've all been there.

However, even those who aren't exercise physiologists appreciate the difference in how we feel after a 3-month trip as opposed to a 10 day trip. Especially as we get older, effects on the cellular level in muscle and brain and other tissues of a prolonged period with hours of daily exercise simply leaves us much more fit, healthier, and feeling better. At age 65 on my last trip, I didn't get into the swing of things until about week 6. By week 8, I felt unstoppable. (And those who have spent a year or more on the road will tell you that it left them feeling more fit than a 3 month trip.)

[John Nelson]

The biggest logistical challenge of many bicycle tours is getting to the start and getting home from the finish. The most significant argument for me against the section approach is having to do that over and over again.

[djkotze]

Invite him/her to join you

[froze]

We're all aging quickly, and in a blink of an eye, it's eternity.

You didn't say how old you are, if you know you're going to be retiring soon, then forget it and retire now, if you can't retire yet then you need to stick with your job, they need you and you need them.

Starting a business is also very risky, it could eat up your retirement nest egg only to file for bankruptcy later, then everything is gone, and your wife might be gone too! 

About 20% of all businesses that start fail in the first year, another 60 or so percent fail between the 2nd and the 3rd year, the odds are not in your favor, you would have far better odds at the blackjack table!  The odds I quoted are all over the table, depending on what you read, a couple sites said that about 25% of new upstarts are around 15 years later, that's a bit better odds than others I've read, I remember when I was in college back in the late 70's and early 80's a professor told us that only about 12% of all new upstarts are around after 15 years, not sure if things changed since then or people are just throwing out numbers.  Regardless, there are significant risks involved with starting a business.  You also have to be prepared for low personal income, something you don't have to worry about right now, so it could be a real burden to suffer personally for X number of years.  It could take you 15 to 20 years to get up to the kind of income you're making now, then you can't leave the business to go on a bike tour because the business needs you 10 hours a day 7 days a week.  Been there done that!

If you go the starting your own business route, make sure you isolate your retirement from the business, in other words, do NOT use your retirement nest egg to start, or keep your business running, or give you income to live on.  Also do not take a second on your house to start a business because you are putting your home at risk of losing it.  You will need a business plan laid out professionally, and get a business loan if that's what you need to do.  Make sure the business is put into an LLC, then if you default on the loan the collectors can't come after your personal assets as long as they're not connected.