How To Know If You’ll Love Your Dream Job

Ever fantasized about marching into your boss’ office, handing in your resignation, packing up your life and running away to some exotic location to do something totally fun? Before you sell your possessions and run off to Bali to teach yoga, wouldn’t you want to find out if it will be worth it?

If your like most of us, we have these escapist fantasies more often than we’d like to admit. But we never actually do anything about it. In fact we come up with a million reasons it’s a terrible idea.

“What if I hate it?”

“I couldn’t afford to do that and still have all the things I want…”

“I’d have to start all over and who wants to do that?”

Nope, you want low-risk and guarantees. You’d have to know for sure everything was going to work out before you made your move.

I get it. When I was still in the corporate world, I used to fantasize about running a little Bed & Breakfast in wine country. Of course, I never thought that would ever really happen. Well, you know what they say…careful what you wish for.

My boyfriend Thom and I are extremely blessed to have the freedom to work from anywhere. So when Thom’s uncle became ill and we wanted to lend some love and support, a crazy idea popped into our heads. Why not pack up and move to San Diego for 2 months to help them (you guessed it) run their Bed & Breakfast in our “off hours.” In just 10 days, I had my hands in everything from marketing, to painting porches, cooking and cleaning. It’s everything I ever wanted to know (and never knew I needed to know) about running a B&B.

Now, I get that 99% of the world doesn’t have the freedom and flexibility I do, BUT this little adventure got me thinking. There are lots of other ways you too can try out your fantasy job and eliminate some of the uncertainty without taking the plunge.

  1. Talk to people doing it. You wouldn’t believe all the things I learned from casual conversation with Thom’s Aunt Kate over dinner one night. I learned all about how they got started in the B&B biz, what their long-term plan was, what she’s loved about the work, and even the stories of their craziest guests. And that was just over a couple fish tacos. Imagine what I could have learned if I had gone into it with even a short list of questions. So, get curious and write down the biggest questions you’d want answered before even thinking about actually chasing that dream job. Then find someone that does it now (or something close to it), and just ask. If you don’t know anyone personally, you can find all sorts of stuff if you just Google for interviews and case studies of people living your dream.
  2. Moonlight. It may sound crazy, and I know you’re already super busy, but there are plenty of small business owners and organizations that would be more than willing to let you put in some work for them on a weekend or would even hire you part-time. Just being “around” the B&B, I easily put in 15-20 hours a week simply asking if there was anything I could help with and I got to see what the reality of what the day-to-day is like, rather than imagining it. Priceless!
  3. Be a Shadow. Don’t have time for a part-time job? No problem. Just find someone to follow around for a day or two. People love to talk about what they do, and this is a great way to give them that chance and get some first hand experience without an extensive time commitment. Worst case scenario you use a little vacation time and realize it’s not for you, but isn’t it worth it to get the behind the scenes view?
  4. Test it on your Friends. If all else fails, and all other options are dead ends, why not just invite some friends over and “try out” what you think you’d love to do with them? If it’s running a B&B, invite them to come stay for the weekend and take care of their every need. If it’s being a travel guide, plan an amazing trip for a group. If it’s having a little boutique, maybe you buy some items and have a “sale” at your house or offer to do a little personal shopping for them. Is it exactly the same? No, but it will still give you more information than you have today to chew on.

So what is YOUR escapist fantasy? If you could take a week off and “try on” something you’ve always thought would be fun, what would it be? What things would you want to know if you could “try it before you buy it?”

The real truth is you’re never going to know beyond a shadow of a doubt that anything will pay off exactly how you want. And you’re never going to have a chance of ever having your dream job if you never take the first step to learn more. Don’t you owe it to yourself to make a small investment of time to explore it just a little more before writing it off forever?

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