To Vacation or Not To Vacation

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I didn't know where else to talk about this (my parents are out of the country and my co-workers are no help). Earlier in the year, I made a decision to go to Tokyo next January for about 10 days. Being a fan of videogames and anime, it's a place I've always wanted to visit (plus there's a really big pro wrestling event going on there). I was waiting for the days to get closer to make the actual arrangements (not too close, six months out), but I've hit a few psychological setbacks. Money's not the issue nor is it any other travel-related fears: it's that I have no more confidence that my job can survive without me for that amount of time.

In short, I'm the accountant/office manager for an office furniture installation company. I own my own business, so I have as much PTO as I could want. However, I took a week off work earlier this year and it took a REALLY long time to catch back up and re-center myself there. To make matters worse, I took a DAY off earlier this month and ran into similar troubles when I came back. I'm not blaming my coworkers since I consider them my friends, but the spark of excitement that came with the anticipation of the trip is gone.

My parents really want me to go, but I honestly believe that my added responsibilities in the office requires me to stay here. I'm at the point where I honestly don't know what to do anymore. Well, I better stop before the tears start. I am at work after all.

Wow Tokyo is a place I would love to visit someday, I'm jealous!

You should definitely go, life is so short and should not be wasted. If you get the chance to travel, definitely do it, it's worth every minute.

As you are the office manager, surely there are people you can delegate tasks to, aren't there? And this includes when you get back, right?

I mean - was it because they did something wrong, or was it because it was different from the way you would normally do it? And is there any way you can set things up ahead of time on like an "in case" situation?

That said, I agree, going away is tough because the thing is, trips are great, but then there's that coming back part that is hard. For me, I travel at least 3 times a year, so that involves not only planning for the trip itself, but for the work coverage while I'm gone, and yes, it does indeed suck. But it is worth it in the long run. Isn't there a way you can do this too?

YOU HAVE TO GO!
There are no worse things than what ifs.
If you don't go you will regret it.
Maybe you could take a laptop with you and check in every morning, or even work an hour daily to keep yourself up to date. Next year January is far away, you can arrange everything in advance.

Or let me rephrase it. What's worse? A lifetime of regret or maybe 2 months of catching up with work?

You have half a YEAR to train someone else on how to do the ESSENTIALS of your job to keep the place operating while you're gone. Train someone (or two), delegate, relinquish control and have faith in someone else' abilities to get things done well enough to keep the place running.

Otherwise you are not a business owner, but rather, you're self employed. That's the difference. Owners own a %, or all, and others manage/work the jobs. Self employed people have essentially bought, or created, themselves a job that they must be present to do. Shift your thinking more from a self employed perspective to a business owner over the next 6 months and set things up so you can take a proper vacation and not worry.

It might be as simple as scheduling things for 2 weeks further out than you normally queue up if you only schedule things for x amount of time right now.. plan all the work for while you're gone well before you leave and then leave the plan with your people to execute.

Even if you were running an emergency room, there should be backup plans and people trained and able to take over very basic functions of keeping things going should you get sick or injured yourself.

You have half a year to sort this out. Book the trip, buy the tickets, then deal with planning so the essentials get done while you're gone and you come back to a few receipts to file & account for or w/e. It shouldn't be total rocket surgery stuff here, but if you're having difficulty planning and scheduling and making it work - come back and post here and we'll sort it out.

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No for supporting trump. Because doing so is deplorable.

I suppose I should provide a little more detail on my job. We only have five full-time employees in the office not counting our field employees. My dad essentially bought the business in 2012 just so my uncle and I would have something to do professionally. His assistant is loaned out to us as one of the office employees, but she's basically the middle person between the staff and my dad (who serves as an advisor, though personally I think he's more than that). That leaves my warehouse manager and ops manager (who were pretty much here before me), but those two can handle themselves for the most part.

When I've gone on PTO before, I had a lot fewer responsibilities than I do now (which is why I believe taking time off wasn't a problem before). I took on a good chunk of the workload since my uncle (who's probably the most neuro-typical of us all) was spending 14 hour workdays trying to figure out things like invoicing and billing which I was able to take to like a fish to water once I molded it into a system that fitted me. Good news was that I was able to fill the role my dad had envisioned for me, but it came at a psychological price.

Dad's assistant is the one who would (in theory) handle the workload if I wasn't there. She's bipolar and a stepmother of two, so I try not to lean on her too much out of respect for her and her family. However, we've had a bit of a rift form as we've gone along. She's mentioned that she never looks forward to me being away since I have so many responsibilities she would need to cover. And all that's before going into the things she changes about my layout while I'm gone.

Yeah, I know that this is a first-world problem. But it's the rut I've fallen into nonetheless. The mind doesn't care if you're in the penthouse or the outhouse.

Do you have the financial capability to possibly hire a temp worker? Because that may be worth it as well, to have someone who is familiar with accounts payable stuff and could be trained ahead of time on your particular way of doing things so you can take off for a few days.

I am familiar with your problem. I own a small business with five people working for me. Preparing to leave for any time off was virtually impossible until I got enough people trained to do the work without me. I worked seven days per week for three years before I took any time off. But I have learned now, how to delegate, let go, let others do the work. It might not be exactly the way I would have done it, but that is okay too. It was nerve-wracking and I hovered too much, made sure there were backups of backup plans for every possible thing that could go wrong, even bringing a satellite phone with me when I went places without phone service so I could be reached.

Now, I pretty much just email the team the days I am going to be gone and let them handle it. I am going out of the country for three weeks and will be totally unreachable in the Canadian wilderness. Do I still have some internal stresses and anxieties - of course I do. But I keep on because that vacation time is so essential to my overall well-being.

And if you get sick, injured, or called away by a family emergency or something then they have no choice but to just deal with it.

At least with a planned absence you can PLAN. You have half a year to figure out who to delegate what essential tasks to and train them to ensure they'll be done smoothly while you're away.

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No for supporting trump. Because doing so is deplorable.