Choosing Your Own Career Journey

What do you want to do with your life? 

Who hasn’t dreaded hearing this question? Finding the answer can take many forms: a buddinging talent during childhood, a sudden epiphany, a meandering life-long quest. Often, the choice is specific and fairly well-defined, some thing to aspire to: doctor, lawyer, teacher, painter, musician, football player, and so on. But there are those who find they have many diverse interests that collectively don’t fit any conventional pre-existing category.

What happens when you know the things you want to do but you don’t know how to make your hybrid dream job a reality? How do you forge your own path when the standard options don’t suffice?

My own journey has been anything but predictable. I started out with a natural interest in art, which morphed into a graphic design major in college. My design professor connected the dots between my interests and skills and introduced me to information design. A huge, life-altering door opened before me. I was basically handed exactly what I wanted to do, without knowing that’s what I wanted to do. And there were people out there already doing it. Just one problem: there was no yellow brick road leading to my dream information design job. It was up to me to blaze the trail for myself, to knock on many doors, to piece together clues along the way, to learn from mentors, and to ultimately draw and re-draw my own map of the terrain that fascinated me so.

The 20 year-old me who first set off on this adventure could never have imagined the steep climbs, sudden drop-offs, sharp turns, tedious stretches, hidden treasures, treacherous depths, or glorious peaks I’d encounter along the way. Now, nearly 20 years later, my journey still continues, but there are others about to set foot on theirs and face the same uncertainties I once did. To those who’ve chosen to venture off the beaten path with their careers but aren’t sure how to navigate — the soon-to-be college graduates and mid-career pivoters — in the spirit of Rainer Maria Rilke’s Letters to a Young Poet, here are some hopefully helpful suggestions (generalized for the non-information designers out there).

5 Tips to Launch Your Journey

1) Define what you want.

Flesh out in detail your future state, with as much as you know so far. Visualize it as best you can. What types of projects would you be working on? What skills will you be using? What outcomes will you hope to achieve for yourself and for others? Even if you don’t have all the pieces of the story, it’s crucial to have a general goal in mind that will focus your efforts. This is your North Star. The picture will get clearer with time.

2) Commit to it.

If you know you want something, put 100% of yourself into achieving it. Believe without doubt that you’ll find the way. That’s the only way you’ll get 100% of what you want. Just one word of caution: make sure you’re doing it for the right reasons — because it’s the fullest expression of yourself and your skills, because it taps your highest potential, because it will bring some good to the world. Purely pursuing wealth, fame, or other ego-driven aims will carry its own unpleasant lessons.

3) Assess where you are now.

Methodically size up your situation relative to your goal. What’s already working to your advantage? Maybe you have a strong network of people to tap into. What’s lacking? Perhaps there’s no structured training program in what you want to do. Be exhaustive in your lines of questioning. This type of evaluation can surface clear problems to tackle and opportunities available to you.

4) Plan your initial steps forward.

Once you’ve done your evaluation, you need some sort of working plan that addresses current gaps while drawing on existing strengths and assets (point 5 below lists some essential action items for most fields). There are plenty of guides on planning and productivity, so I won’t go into that here. The main point is to adopt a system — any system you can stick to — and break down your main goal into smaller objectives and even smaller tasks that you can plug into a calendar and chip away at daily. With every crossed-off item from your list, you’ll get just a little closer to your goal. Also, keep in mind that this should be a flexible plan; you’ll need to course-correct as you learn new things and try out different experiences.

5) Get to work.

Read ALL the books (and their bibliographies), magazines, blogs, websites, papers, journals, conference proceedings, syllabi, etc. And by all means, use a real, physical library to do your reading and research, not just because they’re meant for this, but because they allow the possibility of stumbling upon some adjacent book on a bookshelf or table that opens a new door. Bookstores work too.

Educate yourself with continuing ed, summer courses, workshops, online classes, whatever. Experts in your fields or areas of interest can help answer questions and help point you in the right direction. With any luck, you might find a mentor or advisor in the process. 

Apply what you learn in any way you can, from personal projects and trial projects for friends and family to internships/apprenticeships and freelance gigs. Hands-on experience is vital to sharpening skills and zeroing in on exactly what type of work you want to do and where you want to do it. Being in the “trenches” also tests your mettle; every trial by fire that you endure makes you that much more resilient and capable of handling what comes next.

Connect with other people at lectures, Meetups, conferences, and other gatherings. Informal get-togethers make it easy to strike up conversation with all kinds of people and hear fresh perspectives on whatever may be bouncing around your head. Living in or near a big city can afford you a wealth of social options, but if that’s not the case, online platforms provide plenty of opportunities to join conversations. You might come across kindred spirits on similar journeys to your own. 

Participate in groups and organizations that relate to your interests. Volunteer or take on an administrative role. Tapping into these networks gives you access to a variety of members-only resources, such as certain publications, content repositories, and discussion forums. Being an active, visible member of a community doesn’t just mean you can find other people — it means they can find you too.

These five steps are just the beginning. Once you’re on the journey, you need to prepare for what lies ahead.

5 Tips to Survive Your Journey

All is not rosy on the self-determined path. It’s extraordinarily hard work to execute and follow through on a hybrid career plan, churning through tons of information and constantly being in sense-making mode day after day. But there’s also the invisible, unspoken side of things: the inner battle with self-doubt, frustration, and the looming spectre of complete and utter failure. As I’ve learned many times over, remembering a few encouraging words and repeating them every now and again can lift you out of some difficult places.

1) Make sense for yourself.

As you get acquainted with a particular field, you may find that there’s a tendency to cling to conventions and stick to established “insider” concepts and themes. This is not unusual as it’s what most disciplines do, although crossover discussions bridging different fields are extremely rare, in my experience. The connections you seek are up to you to make. Follow paper trails. Find similarities across fields and look for “common ancestors” such as key figures or influencers in their respective histories. Question the so-called “gurus.” Accept no easy answers. Seek out original evidence and create understanding for yourself. The most powerful asset you can have on this journey is an open but critical mind that can synthesize disparate bits of information and reach sound conclusions independently.

2) Come to terms with uncertainty.

The self-driven journey is filled with surprises, some welcome and some not. A promising-looking gig might end up being a total mismatch for you. A golden opportunity to study somewhere might fall through at the last minute. A random conversation with someone at a friend’s party you almost bailed on might open an exciting new door. This is a game of trial and error, where you don’t know until you know by getting out there and doing lots and lots of stuff. You will often have to take leaps of faith (some bigger than others), using little more than your best judgement. Just try not to brace for the worst instead of expecting the best just so you don’t get let down when things go south. Keep an optimistic perspective, because no matter what, you’ll always end up learning something valuable.

3) Get discouraged, then get on with it.

Sometimes, things will just suck. It’ll feel like there’s a mountain of stuff to learn, and life is too short to gobble it all up. It’ll feel like you’re missing something, somewhere, and nobody is telling you about it. It’ll feel like other people are on the express lane to success while you’re barely moving at a crawl. Worst of all, it’ll feel like it’s all pointless, nobody understands or even cares, and you’ll never be good enough. Allow the dark thoughts to pass right through you. Don’t let them hang around too long or get trapped in a rut. Stay on course. Remember how far you’ve gotten, how much you’ve accomplished. Remember the encouragement shown to you by people you respect. Better things are in store for you if you just power through and keep at it. Trust me.

4) Give yourself space.

There’s no race to the finish line. It’s your journey, and you’re moving at your pace (so long as you are moving). Allow yourself to step back — away from the multitude of browser tabs, podcasts, and videos on your screen(s) — and quietly reflect on what you see, hear, and experience. Make use of empty moments of your day. Sit in a park or coffee shop and document your journey with a pen-and-paper journal. Shifting your perspective can help you see the big picture and enable connections you might not have made while deep in the weeds.

5) Pay it forward.

After some time, you’ll look back in amazement at all you’ve done. You’ll see the post-its sticking out of the books you’ve read, the piles of journals you’ve filled, the stack of cards you’ve collected, and maybe photos of people who’ve shared your journey. Now it’s your turn to give back. Publish. Teach. Speak. Mentor. Show the way for the next generation of trailblazers.

The best thing about this journey is that a goal is not a destination. There is no terminal point. It unfolds and evolves as you learn and grow. Where you go next depends on your persistence, curiosity, and creativity.

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