Finding Your Dream: The End Game

We’ve already covered many ways to go about finding that dream job, but there’s one more way to go about narrowing down the endless possibilities:

Decide where you’d like to end up.

Of course, you won’t be able to choose a future and have it automatically happen—life, unfortunately, has simply too many variables for that. But by identifying the kind of “retirement” you’d like, you’ll be able to consciously make key decisions that will help get you there.

I use the term “retirement” very loosely, because a traditional retirement may not be possible or even desirable. Perhaps you’re someone who would rather split work and vacation time much more evenly throughout your life, or you’d prefer to work your entire life to varying degrees. Perhaps you’d like to stop working at 30 and travel the rest of your days. Fantastic! It’s not up to me to make that happen for you (though I would if I could!), but by establishing your long-term lifestyle goals now, you can start identifying the things you’ll need to achieve them.

For instance, how much money will you need to retire in the way you want? Start developing a budget by calculating living expenses, travel expenses, health expenses, etc, while adjusting for future inflation. If it were me, I’d multiply your numbers by 130% to give yourself a buffer in case of medical emergency, natural disaster, or any of the other myriad ways life can go haywire. AARP and NerdWallet (among many, many other sites) offer retirement calculators you can use to estimate what you’ll need, but they’re imperfect tools and require some tinkering with.

Another consideration is the where: Do you envision yourself in a mountain cabin or NYC? Do you want a yacht in the harbor or a yacht as a primary residence? How important is home/property ownership?

Mostly what I want you to think about is the bigger picture: Do you want to be the VP with the corner office? Owner of a beloved local antique shop? Head of a video game studio, or just lead developer? Do you want to keep working at some point, or will you stop entirely?

Once you’ve identified answers to some of those questions, you can answer (to the best of your ability) the following: Are there ways to continue to make money doing what I do now? Do I have skills that would be applicable to part-time or freelance work? Do I have the skills I need to have the job I want through retirement? Are there other ways of making money that would support me in retirement without me working?

I know these things can feel incredibly foreign to someone early in a career, but often an end goal will help you focus. Even if your goal is as amorphous as “spend my life near an ocean,” it will still help you choose between an offer in San Diego and one in Chicago. Or it’ll start you on the path to looking at a career in marine biology, or what licenses it takes to become a sea kayaking tour guide. These are (as usual) random examples, but I want you to use the lens of the future on the lists you’ve been developing, and further refine them into something that gives you a baseline of where to start.

Next week, my dear friend and absolute treasure Morgan Beem shares her experiences on pursuing her lifelong dream (spoiler: successfully) of becoming an American comic book artist!

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