Just Ask

I only studied improv for one semester in college, but I carry with me two valuable lessons from those Friday night rehearsals… the first is to always say “YES, and…” because that’s the only way to move a scene forward, to make it work. True for life, as well. The second isn’t an improv maxim, but logistically can provide more concrete results on the day-to-day; Fairfield’s Director at the time, Heather Parody, told us “you won’t get what you need unless you ask for it.”

And you know when a little nugget of advice plants its seed? That’s what happened.

Six and a half years later I sat down with my boss at work and asked for what I needed: “Can I have six weeks off next spring to go travel?” Without hesitation he shot back “Absolutely, fully support it.”

BOOYAH! I did not think it could be that easy. All that nervousness and held-back hope... and he said YES!

At the time Ralph and I were planning to head to Buenos Aires, rent an apartment and take tango and Spanish lessons, como muy romantico, no? Alas, the major dictator of all budget travel ruled: my financial resources would not cover that destination. No worries, though, there are 5 entire continents (count ‘em) left for me to explore. This time we’re heading to Southeast Asia, where the sun is hot, food is on the street and temples & beaches are bumpin'.

For those of you who are ready to Google “how to ask your boss for time off,” let me give you a few tips to get started:

1. Request a copy of your employee handbook and read through the section on leave. I was surprised to find my company had a policy about unpaid leave (did I mention these 6 weeks off will be unpaid?) that was unrelated to medical and family leave. It should include all the details you need to know on how much time is allowed, what your medical insurance looks like during your time off and also if your job is guaranteed or not upon your return.
2. Soft-sound your HR contact before reaching out to your manager. In my case, my HR manager was able to tell me that people request leave all the time (just not in my particular office) and that she fully supported the adventure. But in the end, it was up to my boss to approve.
3. Prepare “The Ask” for your boss. Make it easy for him or her to say YES. Ask as early as possible and give an outline of a plan for coverage while you’re out. I asked about six months ahead of when I wanted to take my trip and there is ample time to prepare my work to be transitioned to other team members. Then it’s the fun part of the conversation – talking about the trip. Your boss is a big reason you’ll be taking that longer-term trip and if they said yes then they will likely also be excited for you… share your enthusiasm, joy and appreciation.

Now that I’ve secured all approvals, it’s so fun to talk with my co-workers about my upcoming journey: getting tips, hearing stories and connecting. Which is bottom line what makes traveling so enjoyable and satisfying in the first place.