Why You Really Need A Backpack, not a Parachute, to Transition Careers Successfully

How to survive the unsettling phase no one likes to talk about—the murky middle.

Photo Credit: Ezra Jeffrey

I have spent the last few weeks doling out episodes of Transparent Season 3 to myself like they’re the last box of chocolates ever made. I love so many things about the show, but one of the most interesting for me on a neurological level is hearing the phrase, “I’m transitioning,” repeatedly. I find it soothing. The statement that owns a process not yet completed, a journey mid-process. Obviously the characters are using it in an entirely different context, but it’s the only space I’m aware of where the idea that leaving behind being one identity and becoming another needs to be given time and space.

Two years ago I ended a successful run as the co-author of numerous commercial fiction titles and started a coaching business so I could separate out my art from my income and use my time to create work I care deeply about, regardless of the marketplace. That sounds great, doesn’t it?

On a daily basis, as something actually lived-through, it was a profoundly messy and non-linear experience. But I learned a great deal about how to create effective, lasting change. And building a new identity that’s a better fit than the old one.

I found the most helpful first step was admitting to myself and my community that I had run out of road. And, at that exact moment, I did not know what was coming next. I did not have a clear action plan. Just a yearning. And a lot of fear.

I found the most helpful first step was admitting to myself and my community that I had run out of road. And, at that exact moment, I did not know what was coming next. I did not have a clear action plan. Just a yearning. And a lot of fear.

And this phase did not last a weekend. This phase lasted for months. I had to push myself at parties to say to friends and family, “I know we are writing our last book together. I know I’m on the cusp of big change, but I have no idea to what.” This is a very uncomfortable step and as a culture we like to skip it. We deeply dislike not knowing. We want test results back fast and we hate undecided voters.

So why do it? Why not just keep our pending change under wraps like a butterfly, and do the awkward part in private until we can bust out of our chrysalis with new business cards?

Because, I would argue, that getting vulnerable is part of shedding the trappings of your old identity. Whatever you are doing now probably comes with a lot of status, or at least security. At the very least predictability. In order to change you have to loosen your relationship with those things. They most likely will come back, but possibly not immediately, and if they are what you are focused on maintaining I posit that your next phase will end up feeling you’re your current phase.

While you’re owning that change is afoot, this is also the time to get clear and honest with yourself about what you want to keep in your next iteration—and what you are ready to let go of. And it may not be obvious! One of my clients, let’s call her Pam, had been in fashion media for decades. Pam knew she was ready to leave her company when she found herself answering to a woman half her age. Pam immediately let it be known across her industry that she was available. She went on interview after interview, but nothing excited her. Then she realized: she didn’t want to do the same job at a different place. She wanted to use the expertise she’d gained over the years in a whole new way. So she opened her own fashion consultancy—helping emerging designers make an impact cost-effectively. She finds it gratifying at a whole new level. Did she survive an income drop of almost half for an entire year while getting up-and-running? Yes. Was that scary? You betcha.

It wasn’t the obvious move and it wasn’t the safe move. But it was the move she had earned with the investment of her years of experience.

So stay honest and stay curious. And get out of your routine—even if it’s just to take a long walk in the park—and ask yourself what you really want this next phase to look like—unencumbered by what you think is ‘realistic.’ My partner re-entered the corporate world at a high salary after a 15-year absence. She did it by holding a clear vision of her worth—even while everyone was telling her she should consider herself lucky just to be getting hired. She refused to buy into that narrative.

The third strategy is not to ask yourself what you want, but what you have to give. This does not mean you’re going to give it away for free. It just allows you to take stock of what your ten thousand hours are, to borrow from Malcolm Gladwell. So often we get on a treadmill of performing our jobs and we forget that along the way we are becoming experts in multiple areas. That expertise is valuable.

When I stopped writing I thought, ack! I’m 40 and all I know how to do is write books! Um, yeah. I actually super know that. How to conceive of them, structure them, execute them, edit them, and market them. And a lot of people would like to know how to do that.

My next door neighbor was a professional chef before kids. Now she makes simple, quick week-night dinners that make my mouth water when they waft into my window. When she was trying to think of what to do when her youngest starts school full time I said, “You know, that thing you do automatically that you don’t even think about, making quick, delicious meals, I would pay you to teach me how to do that. And I bet a lot of moms in this neighborhood would, too.” And a cooking school is born.

Allow your new identity to gestate. Growing a baby for nine-months in uncomfortable. Growing your new self won’t take any less time or feel any less awkward.

And lastly I tell you this story: a friend in college was standing on a fire escape that gave way. He was totally fine. Why? He was drunk. The doctors said the best thing you can be upon impact is limp.

It is counterintuitive, especially for those of us who have had to bring so much energy to shifting the needle in male-dominated industries, but try to stay relaxed. Allow this to unfold. Allow your new identity to gestate. Growing a baby for nine-months in uncomfortable. Growing your new self won’t take any less time or feel any less awkward.

That does not mean you’re doing it wrong. It means you’re doing it.

And if you haven’t, watch Transparent. Watch people grappling with the in-between. With having left one shore behind, unsure if another is looming. And finding grace.

Ultimately you know what your present identity looks like. The forward option? The unknown option? That’s where the hope is.

Nicola Kraus is the co-author of numerous bestsellers, including The Nanny Dairies which was made into a film with Scarlett Johanson and Alicia Keys. She is also the co-founder of the consulting firm TheFinishedThought.com, which helps aspiring authors of all stripes build their books and brands.