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Work in Progress: How to Build a Career You Love When Everything is Changing

Posted by

Ana Wang

Published on

January 15th 2020

As part of our ongoing deep dive into the modern job hunt, we've covered defining your dream job. If you're a career changer, there's certain things you should know about looking for a job. And what if you're pretty set on where you work, but want to keep growing? Then, here you go. Next up, we talk to people on their careers and job trajectories. Before we dive in, we bring it all back to the whole concept of a career in today's changing world.

What did you want to be when you grew up? I don’t quite feel grown up yet (even though I should), but I remember flitting from one dream job to another, embracing my curiosity until it came time to decide the rest of my life. Of course, I made the right decision. And I’ve worked hard at that goal ever since, until happily ever after I made it one day and now I’m here to tell the tale.

KIDDING! Here’s the real story.

Past childhood, I found it really difficult to articulate what my dream job was. I thought I knew once, but that led me down a path I realized didn’t work for me at all. So if you were to ask me now, I’d probably give you a very abstract answer. If you pried further, I’d think about it and realize that my dream job could look like many things, but I’d still be hesitant to commit to specifics because by now, I’ve seen just how quickly things change - to expect a static ideal to remain true in an ever-changing world is just silly. To expect that for creative people, well that’s almost “ha ha” funny. Though, of course, you’ll always hear about exceptions: the artist who always knew that they wanted to be, just simply, an artist. (If you pried further, the truth could be that “artist” may have been just one of many childhood dream jobs.)

Wherever this comes from, these childhood fantasies are what first define the direction of our pursuits, sometimes for so long that they become a massively influential part of our lifelong identities. Sometimes we attach ourselves too closely to the shiny surfaces of these dreams, losing sight of the subtext underneath or how the world around us has changed. Or we’ve pulled too far from them, avoiding the whole concept of following our curiosities and tucking the idea of dream jobs into a pocket made for circus performers and secret agents (which, lo and behold: people actually do as jobs too).

So far, we’ve talked about defining dream jobs, and we talked about career changes, but we haven’t really talked about the in-between: a place where things are not so black and white, but instead a beautiful grey area where dreams live and die, and we live through all of it anyway, emerging with feedback the world has given us or that we’ve given ourselves.

And if we listen carefully, we can make great careers out of not one dream, but the layering of many, diving deeper than the shallow “I want to be a designer” and into all the little things that make us who we are: our preferences, experiences, environments, even our insecurities.

Some of us can articulate our goals and dream jobs, and some of us do go through hard pivots and definable career changes. Many of us just keep going, iterating along the path. But, there are very few of us who haven’t had to adapt our dreams in some way, shape or form; that’s not a bad thing at all. It’s not that we’re discarding our desires for the monotonous drivel of adulthood, but a sign that our desires are changing and our worlds are opening up to even more.

I’ve been thinking about this a lot, and especially at SuperHi, where I’m basically living in a sea of aspiration, working to make it real for myself and others: a team looking to make better creative education, students looking to learn and find new jobs, make more money, do more fulfilling work, and me trying to understand how it all fits together and how to do it myself too, over and over again so that I’m not just some creative work snake oil peddler (to be clear: not my actual job description). It’s a place where I get to think a lot about work, creativity and pursuit, all things that weigh heavily in how we measure happiness.

Careers are Iterative

It’s not about the destination, but about the journey, right?

If you went to design or art school, you may have heard this too: it’s about your process and being able to explain how you got to the end. When we teach UX and visual design, with so much to look at, what hiring managers are looking for is, yes, a good end product but more than that, they want to see how you think through a problem. Even when we look at things like code and project management, it matters how clean your code is and how you work through a project, not just what you deliver.

When it comes to careers, how you think and why you make your decisions matters much more than the outcome, an outcome that’s shared by many. You can copy and paste almost anything today, even a dream job just because someone else did it and well, that looks really cool.

But we set ourselves up for disappointment or ineffective striving when we idealize specific and narrow career paths, when we look to our idols and despair when we’re not nearly close enough to where they are, when we see another 30 Under 30 list and wonder how far you’ve strayed and why not me. No matter where you are, whether you have a job you love or you don’t, if you’re young and starting out or mid-career and done, you are still changing. Wherever you are, it’s not the end. It’s time to think iteratively and sharpen your career building process.

If you’re a designer, marketer or product manager, you may have already worked iteratively, a method that doesn’t seek to know everything right away, instead using small experiments and the feedback you get back to improve. If you’ve ever worked at a startup or started your own business, you may have firsthand experience with the downfalls of a non-iterative approach: for example, working months or years on something nobody wants. Well known brands and businesses have met their demise by focusing on wrong outcomes, Blockbuster and Kodak to name a few.

It’s not just business and human nature that demands we think iteratively. Work is changing, just as you are, and just as I have now seen more of the world and the options that are ahead of me no longer as clear-cut as “writer” or “designer”. Entire industries have disappeared and new ones have replaced them.

There are a few key concepts and trends in modern work that will dictate and inform what jobs are and what they mean to us, even how we get them. To share just a few:

  • Freelancing is on the rise
  • Hiring continues to be expensive and time-consuming
  • Remote work is on the rise
  • The internet has made everything more transparent and accessible
  • Traditional education is no longer the only way to learn
  • Automation is here
  • And so on…

TL;DR: Everything is changing and will continue to change in the coming years. What we thought work looked like no longer holds true, and we’re in a brave, new world.

Out of the four people we’ve interviewed for so far (with more to come!), there were some patterns: tapping into intuition and following curiosity, having a strong and clear sense of self-awareness, and using the latter to guide, in an almost organically unfolding process, their careers. They listened when they were curious and when they were dissatisfied. They tuned in when they had something to say, or something they wanted to try.

And that’s what successful careers seem to be built on: a rinse and repeat cycle of exploring, listening and trying. Even then, it was clear that “success” itself is iterative: once you reach one goal, another is laid before you. To play on another oft-cited saying: when one door opens, so does another.

Self-Employment Isn’t the Cure-All

A few weeks ago, we surveyed the SuperHi community to hear your thoughts on dream jobs and the job hunt process. It seemed that the majority of you just want to do your best work, but some turned to freelancing because in that moment, shunned by work or simply disappointed by it, you feel you have no other choice. You showed a different side to the renegade, fearless freelancer living their best life scenario: sometimes, you are there because you’ve been let go or underpaid, unchallenged or overworked. Many did it to escape a hopeless situation, disenchanted with jobs and managers, doing work you don’t believe in or feeling undervalued. That echoes a common motivation for jumping into the world of independent livelihood:

“I did it because I can’t work for anyone else. Because I had to.”

Estimates show that the freelance workforce will keep rising, with some projecting it to make up 40-60% of the global workforce within the next few years. Great! More flexibility for the people who want it, right?

Sometimes circumstances shape our perceptions of what we can and can’t do and yes, there are times and reasons when freelancing and entrepreneurship are the better fit. Sometimes, it can be seen as the “easier” - cognitively speaking - path. Avoidance is one way to escape less than ideal, even toxic, work environments. I don’t say that lightly. People who’ve done it, myself included, will tell you that there’s pros and cons but it isn’t exactly a walk in the park.

But this Millennial “quit your job” fantasy isn’t even a dream for many people: for the many immigrant families I grew up with, starting a business, taking odd contract jobs without security or benefits, was the only thing they could do to put food on the tables. A good job was the ultimate fantasy.

Now, somewhere between steady jobs and passionate escapes, there’s an interesting thing happening: all sorts of fantasies seem to be merging together.

I used to work for a company that built products for entrepreneurs. Entrepreneurship was deeply ingrained in the company culture, from how it started to how we hired and even to how we worked - we encouraged side hustles and taking ownership. Isn’t that funny? A job about entrepreneurship? Except that more and more, entrepreneurship is a mindset that can be applied at work. We need value creators in job settings, working together and not constantly competing. Your value can be amplified within the context of a job, getting to work on problems that have already been deemed financially viable, working with a team and people whose skills and values complement yours. Together, we did more for entrepreneurs than I could myself. My value, and thus the money I received in return to do a job, was compounded within an organization.

This is just one example of a concept that most people find in contrast to the idea of a “job”. Other things - flexible work, artists with jobs, creative autonomy, and freedom in where you work - are all a part of the modern job lexicon, redefining what the picture of work looks like for many people. When companies embrace work that works for people (ie. work/life balance as an expectation and not a disparaged ideal), many of the allures of freelancing are no longer unique to the self-employed. The lines between jobs, independence, flexibility, impact, even money are blurring.

But then there are the questions: how exactly do you get to those great jobs, the ones that offer the things you believe will get you to your best work? What does it take to get the cream of the crop jobs?

Everything is Data

My rabbit hole led me to a TED Talk by mathematician Hannah Fry. Time for a lesson on dating: you have the highest chance of finding the right partner if you automatically reject the first 37% of people you date, so says math.

There are some obvious flaws to applying this to jobs (Does this mean reject the first 37% of companies that offer you a job ever? Probably not). But the overarching point is: don’t settle on what you think is perfect. As you move through life, what you need from a job fresh out of school may not be the same as what you need 5, 10, 20+ years in. What you need to be fulfilled, to fuel the change you need, to match the growth you want, will be fluid over your lifetime. (Good thing jobs aren’t as permanent as marriages, eh?)

The question of what you want and how to get there - it’s a big question, and it looms especially heavy when we’re young, fresh, uncertain, changing, starting. But the great thing is: you don’t have to get it right the first time, or even the second, the third - as long as you iterate, pivot and listen (to yourself) carefully.

You’re a constant work in progress. Take a long term, long view approach to your career, and use each job as a piece of data in that experience. Besides, the definition of a cream of the crop job, as I hope you have now started to discern, varies from one person to another. I’ve seen it myself: two people, in the same job, with the same manager, doing the same work. Guess what? One loved their job and one didn’t. One saw issues where the other one. One appreciated certain things where the other didn’t. No one was right or wrong.

Learn from Others, Learn from Yourself

Two of the most important questions you can ask yourself, anytime you feel stuck, anytime you look around and wonder why you haven’t “made it” yet: What piques your curiosity? What do you want to try next?

While there’s no secret, no hack and no consensus - and certainly no one grand fairy tale ending (it’s more like a choose-your-own-adventure game with many possible endings) - you can build your self-awareness and diversify what you know by learning from those who’ve done it and then trying it yourself. So this is where we’re starting, as we look to kick the year off by saying it’s okay to not know where you want to end up, as long as you try to work with what you want to do next.

We’ll be giving you an inside look at people working in jobs with diverse models: from managers to makers, big cities to the middle-of-nowhere, remote work to cubicles. We’ll be examining creative work in jobs, as well as how jobs support creative side projects. Our aim is to show you the things you may not have thought of, the things you may not have considered and the things you have and want to know more about. And from that, to give you more information to build towards the next step in your own iterative career. Beyond that, we’ll continue to explore modern career paths in the context of the technological and social changes you’re living today: we’re going to talk about freelancing, career changes, getting your foot in the door, and what to do when you’re facing burnout.

An iterative career expects agility, feedback and research. An iterative career expects you to change your mind. And it needs you to go for it, to put yourself out there, to do the work, in order for you to get something back.

Through it all, you may not have one dream job but many. You may love your job until you don’t. You may follow your curiosity with one thing, falling so hard and so fast until one day, something else catches your attention. Your dream job is a journey, and it’ll change over time. But if it comes down to two things that make up the concept of a dream job for everyone, it’s:

  • How you feel about your job and the time you spend there
  • What your job allows you to do with the rest of your time not spent there

    Sounds simple, right? We’re working on it.

    Did you miss the rest of our dream job series? Learn how to define your modern dream job, then prepare yourself for your job hunt as a career changer, and finally, how to find a job and grow while sticking with one company long term. Oh, and by the way, if you want to tell us about your career journey, email us at [email protected] - we’re always looking for stories to tell. 💌