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

[hoverbird]

I hold a key position with a small company and want to do the Trans America Bike Race, 2021. I am the only one in the company in my position, and have been with them for 5 years. It took 2-3 years to become efficient/effective, and the company is growing. I enjoy my job, appreciate my employers, and feel appreciated by them.

The summer is also our busy season, so my absence could have a significant impact. I don't want to have to find a new job, or start my own business, but I really want to do this ride, and I am aging quickly.

Do you have any experience with this? Can you offer any (realistic or sarcastic) advice?

[John Nettles]

Couple of things.  Do you want to do the TransAm Bike ROUTE or the TransAm Bike RACE (Race Across America)?  They are different.  One is a tour and you can take as little or as much time as you want. The other (RAAM) is a race and takes I think around two weeks. 

I am assuming you meant the Route or tour.  Now for your answers (and mind you I am an avid bike tourist).  If I were you boss, based on what you have said, I would say pick what is more important to you, i.e. the bike tour or this job?  You would be leaving me in our busy season and since you are the only one in your job (you imply it is important) your presence would be definitely missed. 

That said, what about doing it in 2-3 week stages?  Many have done it this way.  One benefit to this method is you can always pick the "optimal" time climate wise, i.e. Kansas in September is much more enjoyable than July.  The drawback is that it can take years to finish and you spend a few days each stage traveling to and from.  Are you able to do any of the job remotely so you could more a few hours a day online? 

Finally, you do not say how old you are but that you are "aging quickly".  People in their 70s regularly ride the TransAm (non-covid years). 

Tailwinds, John

[hikerjer]

I think John has it right. You have to pick what's most important to you.  If you're fairly young, you can always do it sometime down the road but that's fraught with danger as well. Easy to keep putting it off forever. On the other hand, who knows what your employment opportunities will be in the future if you quit your job now. Either way, it's taking a chance.  Again, what's most important to you. At the very least, approach you're employers with the idea and see how they feel about it. Life is full of choices and it's not often easy to tell which is the right one at the time.

Whatever you decide, best of luck.

[staehpj1]

I took 73 days to do the Trans America.  I figured it might be career suicide, but I had a lot of leave saved up (not enough) and decided to go.  I told them I was going and asked them if I would have a job when I got back.  I had been there a long time and fortunately had a uniquely matched set of skills to the needs of the job.  Also I am a hard worker.  It turns out that I was really missed and it was actually good for my career because in my absence they figured out just how much I did.  It could have gone the other way though.

[John Nelson]

Couple of things.  Do you want to do the TransAm Bike ROUTE or the TransAm Bike RACE (Race Across America)?  They are different.  One is a tour and you can take as little or as much time as you want. The other (RAAM) is a race and takes I think around two weeks. 

The Trans Am Bike Race and the RAAM (Race Across America) are two completely different races, at different times, on different routes and with different rules. But, as you say, they are both different than the TransAm route.

[John Nelson]

I did the TransAmerica Trail in 70 days in 2010. A year in advance, I started telling everybody, including my boss and his boss, that I would be gone the next summer. I didn’t make a big deal about it. I didn’t ask permission. I just spoke of it as if it had all been agreed to, a done deal. I spoke of it over and over again until it was ingrained in everybody’s knowledge. When the time came, everyone was expecting it. When I returned, I just went back to work as if I had just been gone for the weekend.

[jamawani]

With a smile.

[John Nettles]

The Trans Am Bike Race and the RAAM (Race Across America) are two completely different races, at different times, on different routes and with different rules. But, as you say, they are both different than the TransAm route.

Didn't know that.  Thanks for enlightening me.  Tailwinds, John

[zzzz]

I took off 5 weeks to take a long bike tour for 7 years in a row. I was working in a 15 person shop where I was the only draftsman, the primary project manager, and would work in the shop a couple hundred hours a year when we were desperate to make a deadline. If the owners of a company find you invaluable they will do their best to accommodate.

I did my part, for weeks beforehand I put in the time to stockpile drawings. And when I came back I had to get caught up, that said, there were people who had to pick up some slack, mostly the owner on project management but they did it because what I brought to the job the other11 months of the year.

Three years ago I opened up my own 1 man shop to build furniture of my own design to sell thru galleries. I haven’t been on a bike tour since. No use talking to the owner, he a jerk! 

Pete

[Westinghouse]

I have no idea. Your details are too general and vague. We do not know your boss. We have no ideas about the rules and regulations. If all you do is tell that to your boss, it seems more likely that you would keep your employment. If you were actually to embark on your adventure, that would be a horse of a different color. You cannot keep your job and bicycle across the continent of north America at the same time. You have to do one or the other. Job waiting at the end of the tour sounds good.

[staehpj1]

I will add that I changed jobs with in the same organization at some point after my Trans America.  When I interviewed for that new job I made sure to tell them that I had a practice of using my leave in big chunks and expected to do the same in the future.  I described some of my past trips so they would have an idea of what to expect.  By then I was getting 5 weeks of leave per year and was able to carry it over for longer trips.  The job I was applying for was one I had held some years previously and they were anxious to have me back so my new supervisor quickly agreed to those terms.

None of my trips were as long as the TA, but I often did longish tours or other types of trips.

As luck would have it the next tour after that supervisor left the new guy said "I don't see how we can let you go for that much time at once".  I won't detail the negotiation, but I did the trip and kept my job without much effort or stress.  It was also clear that I would continue to do so in the future, but I think there was only one more long trip before I retired.  I will say that it required that I be firm and take a risk.  I had lots of allies in what is a very large organization so there would have been the possibly moving to a different department.  Also I think I could have plead my case before my supervisor's boss, HR, of maybe ever taken legal action.  If it had come to any of that I would have been able to document that my accepting of the position was conditional on my flexibility in leave usage.  It also helps that leave usage was generally pretty flexible there.

[HobbesOnTour]

You could, you know, try talking to your boss?
Explain your desire and look to see what is possible. Perhaps they have plans to spread your responsibilities around?
At the very least talk to them. Then you'll have solid information for making a decision as opposed to speculation.

[jamawani]

I was in the same situation, and my employer just let me go.

Just FYI -
"My employer just let me go" has two completely opposite meanings.
I believe you intended it to mean, "My employer allowed to to take the time off."
But it could also me, "My employer fired me."
;-)

[BikeliciousBabe]

I suggest asking your boss for a leave of absence, rather than telling him/her you are taking off.

Note that you might have to fund some or all of your own benefits during your time off.

[Pat Lamb]

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.