In Pursuit of Change: How to Job Hunt for a New Career

We don’t follow one path from graduation to till death us part, our work lives tied to a singular declaration of a lifetime’s worth of identity. How wondrous the concept! That we are not beholden to ourselves, and that, in every moment, we are never too far from reinvention.

The idea that we are active creators of our worlds, even past the point of perceived social or cultural no return (an imaginary line, to be clear) is wonderful, and I think it says a lot about the human drive to grow. Me? I’ve never been much of a risk-taker; I’m pretty risk-adverse, so all my job changes have been iterations more than complete reinventions. Both are completely valid ways to make a career change.

Either way, you’re in some very respectable territory. You could be Cheryl Wischhover, former nurse who decided well in her 30s, with a family and kids and way past the “prime” to start a career in lifestyle journalism, to do it anyway as an intern turned beauty reporter. Or Chandler Bing, Mr. “Transponster” who became an ad copywriter after a moment at a coffee shop where he realized that all his friends loved their jobs and he was the odd one out. The SuperHi team is home to several career changers too, including Mariví, ex-lawyer and now our CX/UX hybrid.

The drive to change spans all backgrounds, income levels, and jobs (there’s not one job everyone hates or one that everyone loves). It afflicts everyone from superstars -

(See: Elvis Costello, former programmer, Julia Child, former CIA intelligence officer and Martha Stewart, ex-model turned Wall Street stockbroker turned well, the Martha Stewart; even the super-rich Kim Kardashian is studying for her next career change into the world of law)

- to someone’s anonymous neighbour next door asking, like I see at least twice a week, some version of “I did it!” or “Can I do it?” on Reddit.

You could be like me, the career iterator, going from one job to another without an active career change approach, but somehow having changed careers multiple times anyway.

You could be, and this is accurate to say: like most of us.

Online education has skyrocketed in recent years (hi, SuperHi!), enabling more people than ever before to tackle their dreams of a career change with or without another - or first - expensive and all-consuming round of traditional college education. People are constant works in progress, and sometimes most of the time, you’re not fully formed enough at 18 to decide what you want to do for the rest of your life. I get that.

But I also get the other stuff: the major imposter syndrome, the anxiety that comes from feeling like you’re too old and over the hill, the constant back and forth, insecurities of wasted time and sunk costs.

Aside from the already pronounced anxieties around finding a job, the career changer’s job hunt is especially daunting. You’re adding some existential questions to the mix: Who am I? Am I good enough? Am I too old? You’re competing with the swathes of people who have trained for a lot longer than you have, with many more hours dedicated to their lifelong pursuit: the purebreds of your craft, we could say. But that first step in, that foot in the door - once you get there, it’s the most beautiful form of validation.

David Epstein posits that generalists are the future in his book, Range. At tech companies, the T-shaped person is often highly desired, someone who has a specialty within a breadth of skills.

This is not to say that if you’re not a career changer that you don’t have these things, but that if you know how to sell yourself right, roles, titles and industries don’t actually necessarily define your work. So what does? Your hard and soft skills, your behaviors, your breadth and agility, what you show up to work dedicating yourself to do and why. And even if you were fairly mediocre, even if you spent years doing what you thought was dead-end work, you’re at least different. Different is good, as long as you know how to work it.

How many times have I wondered what if? If I were more of a risk-taker, I’d perhaps had made more daring career choices, faster. I’d perhaps not spent years pushing my own career dreams to the backburner. I’d perhaps embraced my career change ambitions with more effort rather than skepticism, more seriousness rather than casting them aside as frivolous whim until they pushed me out anyway. Somehow the power of WANT worked. And it made sense not in spite of the time I “lost”, but because of it. This is your pre-job hunt pep talk, signed me.

Welcome to the moment you really put yourself out there, after you’ve made the leap in your mind to then make the leap to get paid for it. So here’s a guide of all the things to consider when you’re in the throes of a career change, looking for the first step into a path that, at the moment, might still seem lightyears away. It’s not. You’re almost there.

Look beyond the obvious job titles

There’s a lot of creativity and free rein given to job titles, and I’m always astounded to discover new jobs constantly, things that make me curious what else could be out there. Who made up these jobs, and when? Does everyone else know what this is? You may be opting for a career change as a copywriter because you love writing and psychology, but there’s now roles in things like UX writing and content strategy. Among these, there are even more granular distinctions between jobs. Or, maybe you want to do some sort of design, so you’ve been looking for “digital designer” roles - but do you even know what else is out there? Sometimes, it may require a bit of extra training but it’s well worth your time to really consider what other job titles may fit your interests and skills - there may be a lot out there beyond what you’re familiar with.

So how do you find jobs if you don’t know what to look for? Stalk the careers pages of your favorite companies, and read job descriptions and tasks carefully. Make note of jobs that sound relevant and close to what you think you might want to do.

Similarly, learn how to describe, in your industry’s terms, what you do (different industries use unique terms, keywords and jargon for very similar roles and skills).

Focus on what your transferable skills accomplished

Studies show that diversity breeds creativity, not just in groups but also in individuals. One of the most undervalued traits in today’s work world is creativity, whether or not employers actively recognize it as that (on job descriptions, it could be labelled as “the ability to work cross-functionally”, “the ability to think critically”, “problem solver”), which means that if you play your cards right, a background that shows you are creative and impactful can really help you stand out. How do you play up your transferable skills in the most optimal way? Instead of just listing skills in your resume, highlight what you did using them in the bullet points under specific roles and in your cover letter and interview.

Things like leadership, project management and excellent communication are fairly universal to a wide range of roles in today’s world, but most people list them and leave it at that. Well, anyone can say that they can do these things, so find ways to tangibly prove it by highlighting results. You’ll notice that these are all “soft skills”. Soft skills require an extra special touch to really make an impact: instead of “I demonstrated leadership skills”, highlight what your leadership skills accomplished. Extra points if you can quantify results with numbers.

“How you do one thing is how you do everything”

An expansion on the idea of playing up transferable skills, the best way to build career capital and to ease your transition from one thing to anything else, according to Cal Newport in his book, So Good They Can’t Ignore You, is simply to be the best at what you do. It’s a vague concept, yes. But I’ve been on the other side of the hiring table and I was always looking to hire for roles that were invented very recently (to the point where what to call the role was always up for debate); there was no precedent or educational path. So what did I end up looking for? Patterns of impact, the desire and capability to learn, curiosity. The type of company you’re applying for and what they value affect what they’re looking for (look for clues in their About and Careers pages, even interviews with founders and key employees), but everyone loves someone who does great work, period.

That’s not to say that if you’ve been pretty mediocre (maybe because you were doing something you didn’t really enjoy) that you can’t dig yourself out of that, but any kind of success is a signal of the kind of person you are: someone who gets things done well. So think back to these things and highlight them, no matter how unrelated they seem (as long as they aren’t dug up from your long gone past, say, anything in high school if you’re past 21). Even though I’ve changed jobs and careers a few times, I still find a way to tie in achievements from previous roles, especially if their results are tangibly recognizable (for example, press features or revenue growth).

Resist the urge to pad your resume. Highlight and focus.

This is general advice but it’s extra relevant for career changers. You’re already at risk of confusing potential employers (especially given my previous possibly contradictory point), so this is the time to revamp your resume and be selective about what you share. You don’t need to include everything - you may find that you’ll need to present an entirely new perspective and narrative on your previous roles. Be ruthless.

This could include things like rearranging your education so that your new skills training comes first. It could mean thinking about what parts of previous jobs are relevant to your new direction, and leaving out things that are unrelated. It could mean dropping certain skills altogether, if they play no part in your desired career direction. Keep your resume focused to avoid the dreaded scatterbrain syndrome, someone who appears to have no focus. Some of you are designers: take the application of negative space beyond the things you design and into how you present yourself. This is the power of a good edit.

Always be learning

If you’re at the stage where you’re already looking for a job, you’ve hopefully already undertaken some skills training, perhaps taken a few courses to upskill towards your desired career.

But, career changes can happen in a way that’s a bit more subtle: for me, they often came in tandem with learning I was actively partaking in, not necessarily as the next step following a concrete learning path. Sometimes, I was doing these things in current roles, taking on new responsibilities and tasks. Whether or not you’re actively searching for a job right now, take the time to consider your career and your next steps. It might not be “change careers” right now, but if you’re unsatisfied and yearning for a change, you might be surprised what opportunities open up when you embrace that learner’s mentality. You become primed for job openings, possibly before you even feel ready - which actually is the best place to be, before you’re desperate for a job.

Talk to people!

People often seem to be more open to discussing their jobs and careers with other people who are new to the field, or even not yet in it. There’s something people generally find very fulfilling about acting in the role of mentor, to people who are starting out. Guess what! You, as a career-changer, are just starting out. And, you don’t get to be here forever. It’s a “for a limited time only” time in the phase of your career.

This could come in the form of informational interviews or job shadowing, but the point is two-fold: to learn more about certain roles or companies but also to put yourself out there and to build relationships. Your next job opportunity may not come the traditional way; it could come by way of a person. Of course, it makes sense that as you gain more experience and grow your network, you’ve worked with and talked to more people and may potentially get to a point where you stop cold applying for jobs altogether, that they come to you. But you’d never know about these if no one knows about you.

Take advantage of the internet to show your work

We live in the digital age. Take full advantage of that to build your career and get yourself a website, if you don’t already have one. This is purely anecdotal, but I definitely think my career grows a lot faster every time I’ve had a website up. And when I don’t have a website, it’s as if I don’t exist at all. It is a strange dichotomy: if you’re not online, you’re probably actually doing quite well and staying busy, but the internet is basically a world of its own, one that connects us beyond physical limitation.

The idea is to leave a trail of breadcrumbs of the kind of work you’re interested in: when I was not yet actively searching for a job but exploring the next phase of what I had become really interested in, I started to orient my personal website and social profiles towards that. I blogged about what I was learning. I had nothing big or groundbreaking to say, but I wanted to at least put forward the start of a new version of myself. Writing about what I was learning also helped me learn.

Sometimes I hate advice like this because it’s always given from the perspective of the advice-giver (me). If you’re not inclined to document and write like I am, do whatever works for you.

• Maybe you’re a strong relationship-builder - so tell your network!

• Or if you’re a visual creative, then the most obvious is to show your work, even unfinished in-progress work.

• If you enjoy writing but can’t be bothered to do the whole “set up a blog” thing, write on Medium or set up a Substack.

• If you’re driven by accountability, maybe do a #100days challenge for whatever your skill or craft is.

I know so well the feeling of not wanting to put out work that’s not done or perfect. I cringe sometimes looking back at some of the work I’ve put out, even work I’ve put out very recently. But output really matters here. The only way to get better and to “get out there” is to do it: put yourself out there, one piece at a time, using your best assets.

At the very least, update the web assets that take minimal effort: social profiles, LinkedIn, whatever comes up when you google yourself. Employers really do look (they probably didn’t a few years ago but the secret’s definitely out by now for anyone who has internet access, in case you’re wondering).

Contextualize your background and tell your story

I recently read a discussion (on Reddit, of all places) about when it’s appropriate to call oneself an artist. Are you an artist if you do it professionally? Or are you an artist if you get paid for it as your main source of income? Maybe you’re an artist if you spend the majority of your time doing it, regardless of your income? The truth is all of the above, depending on who you’re asking, but in the context of a career change, you should tell the story you want people to hear. Find a way to contextualize your experience and frame it in a way that speaks more to what you want to do. It’s never right to be dishonest, but take control of how you want to be perceived.

This in-between space is hard to navigate, because you may not be confident enough to describe yourself as the new you if you’re not yet doing it for money, and yet, your current or previous role just doesn’t feel like the right fit anymore, a too-tight snakeskin you just want to get out of already!

So try this: rather than starting with the common but limiting “I am an x”, talk about what you’re interested in as the lede (bonus points if you do the best thing and apply to jobs that relate to said things), then flavour your bio with your actual work history, highlighting aspects that tell the story you want to tell, the transferable skills and universally understood achievements. Lastly, end by looking forward - what are you hoping to do next? It’s an aspiration sandwich! Give people space to imagine you as the future you. This general concept applies to writing a bio for your website or how you frame your story in a cover letter, even providing talking points for the “tell me about yourself” question in interviews.

For my very first career change (one of many, and probably many more), I went from being an apparel designer to a copywriter. And because I wanted to work for fashion brands, which I ended up doing, I mentioned my design background but spoke about my empathy for designers and approach to brand building. I left out the things I did that I didn’t want to do anymore, so no mention of pattern drafting or assembly production. Gone from my resume like poof! Not one bit. Nada. And I never looked back.

Change your environment

Audit your work “feed” - you can start to train your brain to think as if you’re already in the field/industry by intentionally removing all the newsletters, bookmarks and professional groups you’ve become so used to as past you (just don’t make sure to do anything prematurely) and actively searching for new things to automate your environment.

This is more than “get better at what you do” advice. It’s also a way to prime yourself for finding job opportunities and keeping an influx of them on your radar, as well as getting you in the right mindset for interviews. Being able to speak eloquently about your industry, understanding the “scene” and doing it with fresh eyes and a new perspective can help you stand out big time. As a career changer, you have a lot to give - and while you may feel behind, starting to infiltrate your surroundings with new things related to the field you’re pursuing before you officially get there is like giving yourself a head start.