How To Make A Major Career Change After Your 20s

Changing careers in your 20s is easy, right? Most of us millennials do it with relative frequency—especially compared with prior generations—and we come out fairly unscathed. But as we get older and take on responsibilities like mortgages and children, it can feel risky. If you’re dreaming of a different work life but haven’t mustered the courage to make it happen, perhaps you’ll derive inspiration from this study that found those who start down a new path later in life are both happier and better compensated than those who don’t. It’s never too late—Vera Wang didn’t entertain the idea of being a fashion designer until she hit 40, and Julia Child didn’t learn to cook until she was 36. Here, our best advice for starting anew, taking that big risk and making your dreams come true at any age.

Homepage photo: Matteo Prandoni/BFA.com

Before you start making moves toward a new career, consider why you're dreaming of this new life. There is, after all, a difference between wanting to be a rock star with no prior music experience and wanting to return to a craft you love but shunned in favor of the more responsible choice. This isn't to say the first scenario is inadvisable, it's just important to understand whether the urge is an escapist fantasy or a real calling—before taking the challenging steps to make it happen.

In most cases, we don't advise quitting your job cold turkey to pursue your dream. Instead, pick up some component of your new career as a hobby first. If you want to be a chef, for example, sign up for a weekend cooking class. If you want to be a writer, start writing in your spare time. If you find you're not actually doing the thing you thought you wanted to do—if you're dreading class or skipping your writing session—you may not actually want to do it so badly after all. If you don't know precisely what you want to do, but you know what you're doing now isn't for you, take classes, shadow friends or pick up new hobbies. Experimenting is a safe way to introduce yourself to challenges before taking the plunge.

Connections are so important in the working world these days. Building a network in your desired field is a critical step in transitioning. Seek out those who can advise you, help you get a foot in the door and perhaps most importantly, propel you toward a new life.

This part of the program may involve cold outreach, which can feel awkward, but it's worth the discomfort. Make a list of people at the top of the game you're trying to enter, and reach out to them—DM them on social, e-mail their assistants or cold-call their offices. If you're persistent enough, chances are you'll get a response from at least one. If all that results is a short e-mail exchange or a quick coffee, it'll be worth it—but we suggest you set your sights on someone who has the time and energy to invest. Remember, most will see a request for mentorship as flattering rather than annoying, so you really have nothing to lose.

Now that you've tested out your new path as a hobby, it's time to try getting paid for it on a part-time basis. This might look like freelance or consulting work if, for example, you've always wanted to be an editor. It may also look like catering work or gig work or even internship-level work. Whatever it is, it's not likely to be glamorous, and it's not likely to be easy, especially if you have a full-time job. Still, this approach will enable you to further assess the challenges of working full-time in your new field.

In the age of Instagram success, it may feel as though no one has to work their way to the top anymore, but this is an illusion. Lasting success requires hard work and deference to those with more experience, so you should prepare for both before you quit your current position. Going from VP to assistant is not pleasant for anyone, but it might be a necessary part of the process. Swallow your ego and keep your long-term goals in mind at the expense of your short-term comfort. You could spend the rest of your life advancing in a career you hate—or you could suck up a few months or years of being back at the bottom in pursuit of something you love. The choice is yours.

By this point, you'll know whether your second career was better off as a pipe dream or a side project—or if it's truly what you're meant to be doing full time. If it's the latter, this is the time to leap. Before doing so, we suggest having three to six months' worth of expenses saved, at least; it's important to realize, though, that you're never going to feel fully safe jumping from the known to the unknown, and that you'll never really feel ready. Jump anyway. If you fail, you can always return to the field in which you've accumulated years of experience—and remember that the scariest decisions in life are often the most rewarding.