Landing Your Dream Job After An Awkward Career Change


Jul. 19 2021, Published 4:50 a.m. ET

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Do you remember being 18 and worrying that you didn’t have an answer (or even an idea) when people asked you what you were going to do for a career? Good news! That’s totally normal—most of us don’t just decide on a dream career right out of high school or settle on a field in college and stick with it for life.

According to a recent survey by Gallup, 60% of millennials alone are looking to switch jobs. So, it’s not unusual at all to be thinking “I don’t know what career I want” or even “I need a career change but don’t know what to do.”

Knowing that career change is possible (and probably even inevitable) is one thing. But, when you’re ready for a change, how do you know what profession or career path is right for you? It’s so easy to become complacent in a job or career you’re not really happy with and miss out on a dream job without even realizing it.

So, how can you keep from getting stuck in a career dead-end? And, with all the opportunities out there, how can you know what long-term career path is right for you?

This article (updated from the original written by Elana Gross) shares six tips for how to figure out what you want to do, find a career you love, and overcome the obstacles of indecision and not knowing what you want.


Just because you don’t know what career you want doesn’t mean you don’t know what you’re good at. A great way to focus on your skills is to make a list of your strengths. If that doesn’t come naturally to you, ask a friend or trusted co-worker their opinion. Or check out a self-analysis resource like the Myers-Briggs personality test. Taking an active look at what you’re good at and what makes you tick personality-wise is a powerful way of assessing a career path that will fit and compliment those strengths.

Of course you can be good at anything if you try hard enough or put in enough time. But you can save a lot of time and avoid frustration if you let your strengths lead you to what you should be doing instead of forcing yourself into a career that doesn’t really fit.

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For example, you might have convinced yourself (or let others convince you) that you’re not a math person, only to find out that you love using logic to solve problems. In that case, you might actually have a passion for something like web development that you might have written off beforehand. It’s easy to let preconceived ideas stop you from a successful tech career, but, if you take some time to look at your strengths, you’ll probably be pleasantly surprised by what they tell you.


To help you clarify your feelings about previous jobs, so you can look for similar or different characteristics in the future, answer the following questions about each place you’ve worked:

  • What did I like most and least about the company?
  • What did I like most and least about the industry culture?
  • What did I like most and least about my boss?
  • What did I like most and least about the people I worked with?
  • What was the most challenging thing about working there?
  • When was I the happiest or the proudest?
  • What was my biggest accomplishment?
  • What did I like most and least about my responsibilities?
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Evaluating your past can also help you recall pivotal moments you might have overlooked that would have made it clear you weren’t happy with your work. If looking back starts to uncover negative patterns around a certain kind of job or career, that’s a way to recognize that it’s time to move on. You may very well be missing out on opportunities elsewhere that would be a much better fit with your needs and abilities. Analyzing your past is a key component to discovering the kinds of situations that will bring out your best work and happiest self.


Start taking some time to request and schedule informational interviews with people in the fields you’re interested in to learn about their career paths and get advice. Ask about their job, their professional past and aspirations, and the industry. Just be sure to prepare with with questions in advance so that you get the most out of these meetings or calls and, besides the no-brainer “thank you” afterward, do all you can to find a way to repay the favor.

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And don’t limit yourself to people you know or have connections with. Network at conferences and workshops. Join Twitter chats or Facebook groups. Go on LinkedIn and read people’s job descriptions or read interviews and articles about people in jobs you admire. For instance, if you’re curious about what a day in the life of a WordPress developer looks like, do a quick Google search and you’ll likely be able to find plenty of info and people to reach out to. Before you set your heart on a career—or completely rule it out—make sure you get a sense of what the job is like day-to-day.


Try something new whenever the opportunity presents itself. Take online classes, attend workshops, read books, and watch YouTube tutorials. By taking these chances, you may find out that you’re really into UX design, digital marketing, Python programming—or something else entirely!

The point is that nowadays there are so many options for learning new skills and, by taking advantage of them, you have a fantastic opportunity to find a passion that you can turn into a new career. And, if nothing else, you’ll have a new skill you can use at your current job (and maybe even get paid more for!) or a new hobby that you can turn into a side gig.

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Are people in the workplace you’re considering competitive with one another or collaborative? Are they friends outside of the office? Do they work as a team or on their own? Can people work remotely or are they expected to work in the office? What is the work-life balance like? What are the salary expectations?

These are all important questions for potential workplaces and employers when you’re searching for that dream job to jump start a new career path. It’s also good (and easy) to do some initial research on your own—both about industries in general and employers in particular—using some Google searches and job boards.

If you know you work best as part of a team, then it’s important to find a company that prioritizes a collaborative approach. If you’re more productive working alone, then you might be better served by freelance or contract work that allows you to manage yourself and set your own terms. The same thing goes for scheduling and flexibility concerns. If you thrive in a structured environment and prefer reporting directly to a manager for guidance, then you might look for a traditional, 9-5 job in an office environment. But if you prefer the freedom of working from home or on the road as a digital nomad, and you’re more comfortable being your own boss or supervisor, then looking at remote careers will be key to your career happiness.

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If you aren’t sure where you stand with these things, you can always try taking up work on the side to help you figure it out. For example, if you work in a hierarchical environment now, try doing some solo freelancing gigs and see if you notice a difference in how you feel. And the same thing goes if you normally spend your workdays by yourself—try making some peer connections instead or work on a collaborative side project to test if teamwork might be more your thing.


Two critical questions to consider when it comes to your career are:

What do you love doing so much that you’d be willing to do it for free?

Think about it: If you love something so much that you’d do it without being paid, wouldn’t getting paid for it be the definition of a dream job? Try to picture what that “job you’d do for free” is and then start connecting it to paid possibilities in the same field.

What would make you the happiest (i.e., NOT what would make you the most money)?

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While we all need to pay the bills and, hopefully, still have money left over for a comfortable life, you shouldn’t necessarily choose the most prestigious job just so you can impress people at cocktail parties. Instead, for greater long-term happiness, choose a profession that will make you the happiest and allow you to grow and learn.

So, think about what truly interests you, not what necessarily sounds the most lucrative or high-powered on paper. Try to pin down those things that engage you in such a way that you’re always able to muster at least a spark of passion about them and use those interests to guide you toward an applicable career path.

Finding a dream job should never mean compromising what you stand for or what you want out of your work life, and the good news is, it doesn’t have to. By following the tips above you can develop a clear sense of what makes you tick career-wise so you’ll be able to find a career path that genuinely fits your wants and needs. You may think you don’t know what you want, but with a little reflection and determination, you’ll soon realize that it’s actually right within reach.

This post was written by Kelli Smith and originated on Skill Crush.

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