The Unromantic Reality of Career and Life Exploration

And yes, I still think it's worth it

In The Fellowship of the Ring, J.R.R. Tolkien famously wrote the line, “Not all who wander are lost” as part of the poem, “The Riddle of Strider.” Tolkien was making the point that wandering, even amidst uncertainty, can unlock valuable self discovery and personal growth. It’s lines such as these that create a kind of romantic notion around the process of exploration. And, of course, there is beauty in the idea that we can embark on journeys without a clear destination and come out on the other side as more evolved versions of ourselves, having discovered essential truths about who we are and what we want. Despite what you might be thinking, this is not an essay on the merits of exploration and self discovery. I quite literally write a blog called “No Directions” so I think my feelings on that are pretty clear. All that to say, I wanted to write this essay to explore the nuance and the lived experience of how difficult it can be mentally to explore. Whether knowingly or not, the romance around the explorer’s journey, and how we consume exploration related content, can obscure the mental challenges that mark the explorer’s experience in real time.

As one example, I think about Elizabeth Gilbert’s bestselling memoir, Eat Pray Love, about her personal journey through Italy, India, and Bali following a devastating divorce. While Gilbert wrote quite openly and honestly about the challenging inner journey she went on in the years before and during her trip, I think our perception of that version of her and the discomfort, pain, and uncertainty she experienced is impacted by knowing that there is a best-selling book at the end and eventually a successful movie adaptation starring Julia Roberts! By the time these books and movies come out, there is a clear beginning, middle, and end to that chapter of the explorer’s story. For the rest of us currently exploring, we don’t have that luxury. The story is actively being written. We can’t always look at ourselves with the same positive energy. “Sure, it was uncomfortable but look at the magic and growth and success on the other side” is a lot harder to say and feel when you don’t actually know when, where, and how the other side will materialize (and all the action doesn’t neatly take place within a few hundred pages or a two hour movie).

Which brings me to the question that sparked this essay: What’s it actually like for those of us that are “eat pray loving" or career exploring or sabbatical-ing or trying to figure it out when we’re still in the midst of the action? What’s it like in the during before we know if and when there will be a metaphorical best seller and happy ending? With that, I give you my description of the mental arena of exploration.

• For starters, you have to get comfortable with change. Even if you’re unhappy in the status quo, there is comfort in stability. Change stretches your discomfort muscle to the absolute limit because all of sudden it starts getting used every. single. day.

• Getting clear on what you actually want requires negotiating with lots of fears. You have to do pretty some serious internal work for a sentence like “I want to leave this career” to just mean that and not be so burdened by the weight of thoughts like “I will fall behind my peers” or “People will judge me if I leave” or “What if I fail at something else?”

• The trial and error of exploration is almost never linear and that, in and of itself, can manifest as feeling like failure, rather than a necessary input of hte process. It requires a lot of mental fortitude (and sometimes tears, chocolate cake, and emotional breakdowns) to keep going amidst stops and starts and the persistent feeling of, “Is this ever actually going to work out?”

• Let’s not forget self doubt! If you find someone who’s done significant exploration and not experienced self doubt, please send them my way. They should be studied by science.

• For many people, exploration involves creating an identity that is not purely based on work which, often, means letting go of a long established work identity. If that doesn’t hurt your ego and force you to confront fears about loss of status and prestige (at least initially), again, please come find me. I would love to talk to you.

• Exploration does not fit neatly into a box with a fixed ending and beginning. You can’t just sign up for an “exploration” course, put in a semester’s worth of work, and be on your merry way. There’s a discomfort in the open-endedness of the journey, particularly one that comes without a syllabus and a breakdown of what you need to do to pass the course. Magnify that discomfort 10x when exploration happens over the course of years and generally takes way longer than the timeframe you mentally anchored to initially.

• Exploration typically doesn’t take place in one chapter of our life. To expand upon the Elizabeth Gilbert example, Eat Pray Love was just one chapter in her story. There has been enough life, change, loss, discomfort, and evolution to inform several subsequent books. We don’t just explore once and have it all magically figured out forever.

Make no mistake, I’m glad we have books and movies to inspire us to explore and evolve. I loved reading Eat Pray Love! For my part, I hope that I’m creating my own small piece of inspiration with the stories that I share on this blog. But I’d be remiss to not acknowledge how hard exploring and asking vital questions of our life and work can be when we strip away the romance and the magic and the growth and emphasize the uncertainty, doubt, and fears that inhabit the same space. I’m ten+ years, two careers (and two and half years post quitting a corporate job to start a business), three cities, one global pandemic, and many highs and lows in to my own explorer’s journey. After all of that, I’m just starting to feel like there could be a clear beginning, middle, and happy ending to this chapter of my story. Let me tell you, it did not always feel that way, especially in the many, many moments where it felt particularly unmagical, I swore it was never going to work out, and I had yet to find the trust in myself and the journey.

In “The Riddle of Strider” Tolkien writes, “From the ashes a fire shall be woken. A light from the shadows shall spring.” I wanted to write this post to acknowledge the ashes and shadows we feel before we get to the fire and light part. This post is dedicated to all the current wanderer’s who are brave enough to keep writing before there is a clear manuscript taking shape and brave enough to face the fear before they find the magic. You are not lost.