Feeling Career Confusion? Try a Ten-Year Plan

Everyday Better is LinkedIn News’ weekly personal development podcast and weekly newsletter hosted by Leah Smart, a LinkedIn News Editor . You’ll hear from some of the world's brightest minds and bravest hearts who use science and story to share strategies for how we can flourish individually, in relationship to others and to the world around us. We talk about improving emotional, work, physical and relational health.

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Six years ago, after what felt like falling into jobs with some satisfaction, I decided I was ready to be truly intentional about my career. The problem was, I didn’t know exactly what I wanted to do, nor did I have control over how it would come to fruition. So, I decided to lean on two lifelong practices I trusted: dreaming and writing. I bought giant sticky poster boards and hung them around my tiny New York City apartment. I ordered a mega pack of markers and cleared the calendar for a weekend.

I came out of that weekend with post-it notes scattered on walls, posters with no more writing real estate, and a Venn diagram bursting with ideas from combining my passions, what the world needs, and what I could be rewarded for. Spending time with all the career possibilities was not only satisfying, but it was also invigorating. Having left no stone unturned, I could narrow down what really made sense. There was something liberating about writing down what I’d previously not been brave enough to get out of my head and onto paper.

After the exercise, I gathered the post-it notes in a sandwich bag, folded the posters, and got to work. With clarity around what I wanted, my action steps became simple. Within a few years, it was clear that I was charting a course aligned with what I’d optimistically dreamed of years before. I was in the process of becoming an executive coach, I’d started a podcast focused on my passion for human potential, and a book proposal had begun to take shape.

My experience had shown me that there was something to that weekend practice. It was a combination of choosing to have agency over my career, boldly stating dreams that had been simmering beneath the surface, and putting my energy only into optimism and hope. As time has gone on, I’ve come to know and love a new practice that brings even more clarity than what I achieved over a weekend back in 2018. I was introduced to it by my colleague and host of the Hello Monday podcast, Jessi Hempel , when she interviewed design expert and host of the podcast “Design Matters,” Debbie Millman an. It’s called “Your Ten-Year Plan For a Remarkable Life.”

The plan is an excellent way to bring some of your highest priorities into view. Debbie has her students do it and shares that there are countless stories (including her own) of them coming back to share how much unfolded for them in the roughly ten years after completing the exercise. Having recently done it, I see this plan as a simple yet demonstrative way to express what you want in any area of your life and then to watch yourself move toward it.

Every ten-year plan turns out differently, but it starts with this prompt. Imagine you're waking up 10 years from today living exactly how you'd like to be. Do not hold back. With a pen and paper, describe in detail what your life looks like and how your day unfolds from start to finish. Keep writing until you've gotten everything down that you'd want.

If you're not sure where to begin, consider some of these questions:

• Where do you live?
• Do you have pets, children, a spouse or a partner around?
• How do you spend your morning, lunch time and dinner?
• What do you wear?
• How does your work day unfold?

You can stop this process here and simply read your ten-year plan once a year. But what Debbie advises is to take your ideal day a step further and write steps for what would have to happen in order for it to come to fruition.

As Debbie says, she's not completely sure what makes this so effective for so many, but it is. In my experience, there is the momentum of pointing yourself in a purposeful direction, there's practicality in considering what your ten-year plan will likely require and then there's something inexplicable about voicing our tightly-held dreams. Maybe that's the magic.

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Watch: Hello Monday host Jessi Hempel 's interview with Debbie Millman

Listen: Hello Monday host Jessi Hempel 's interview with Debbie here .

Additional Resource: Your Ten-Year Plan

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Everyday Better is LinkedIn News’ weekly personal development podcast hosted by Leah Smart , a LinkedIn News Editor. You’ll hear from some of the worlds brightest minds and bravest hearts about how to live with more clarity and intention every day, in and out of work. Subscribe to the show's newsletter .

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