How to Begin Pursuing a More Courageous Career
Episode 279 | Author: Lisa Lewis
My name is Lisa Lewis Miller. I’m a career change coach, I’m a long-time fan of Bossed Up, the brand, and the community. I’m so excited to share my philosophy not only on career, career change, and career pathing, but on how to cultivate a courageous career.
We all want to tell a beautiful -- and honest -- story about our career decisions. We want to look back over the decades of work, smile, and feel satisfied with the impact we created and the contributions we made. We want to be truly proud of our choices and accomplishments. However, it’s not always easy to feel a sense of pride in our day-to-day jobs.
Have you ever envisioned your sassy and fabulous 90-year-old self, and what she’d think of your current career choices? If you have, you might know deep in your gut that you’re not creating the career story you want right now. Whether you feel like you’re leaving your potential on the table, or like you’re making sacrifices you don’t want to make, there’s often an opportunity to make the 90-year old version of you proud of living a life and career without regrets. It’s time to make courageous career choices to align your work with your values.
What does it mean to create a courageous career path?
It means consistently using your heart and gut to guide your decisions, instead of externally accepted metrics of success like a C-suite title or a (virtual) corner office. It means channeling a sense of fearlessness and finding a way to double down on your dreams.
If you’re experiencing a sense of discontent with your current career -- whether you’re bored, uninspired, or craving a bigger challenge -- the first step to cultivating a courageous career is letting yourself dream.
What would a fearless career path look like for you?
What kind of career path would feel too-good-to-be-true to you? What feels dreamy and delightful? Everyone’s dream and definition of success looks different: I’ve had coaching clients who wanted to move and work abroad, bring in a full-time salary while working 3-4 days a week, start a nonprofit, lead a company, or take a year-long sabbatical. For each of these badass women, this was their heart’s deepest desire for a courageous career experience.
What are the biggest obstacles that pop up?
Once you give yourself permission to dream big, an inevitable experience happens: doubts creep in. A little voice in the back of your head will start to ask, “Who are you to do that?” “What makes you think you’re allowed to have that?” That inner critical voice pops up whenever we envision stretching ourselves beyond our current box. The biggest concerns that your self-doubt will bring up center around what you “lack.” The three biggest culprits for doubting yourself and sabotaging your dreams are fear of a lack of money, lack of time, or lack of external stuff like resources, knowledge, or connections.
The reason we call this courageous career pathing is because courage is the commitment towards action, even when you’re feeling fear. So part of cultivating your professional bravery is hearing these fears and finding a path forward anyway.
If you get into dreaming and have big money fears pop up, the easiest thing to do is create a plan of what it would take to make your desires happen. Do you know what your ideal lifestyle costs? Do you know the costs associated with your dream path? Give yourself the opportunity to do the research and find out exactly what it would take to achieve. Then, take a look at your current financial situation and create a money plan of how you can take baby steps to enable your dreams to become reality.
Often, we let the fear of financial insecurity become bigger than the reality. And even if the current reality is a little dicey, having a handle on what’s happening and creating a pathway toward future stability and options can feel incredibly empowering.
If your biggest fear is a lack of time, know you’re in good company. So many of us are balancing jobs, family roles, friends, health, and more as competing priorities every single day. And, at the same time, we often assume that the first step towards making a transition is bigger than it is.
Plan your courageous next baby step
While I’m a big proponent of going “all in” on making a change, the most successful changes typically start out as tiny baby steps of commitment. These baby steps can take a mere 10-15 minutes to do, and can create momentum and confidence about your path forward. If you’re strapped for time, is there a 10 minute YouTube video related to your career dream that you could watch today to get more informed or encouraged? Is there a podcast episode about your future vocation that you can have on while you cook dinner or fold laundry?
To make the biggest transformations, start with the tiniest steps: steps that seem almost too small to matter, but ones that are almost impossible not to achieve. If exploring your dream is a priority, there’s almost always a way to carve out 15 minutes in your day.
And if you’re worried you lack the other stuff like relationships or know-how, it’s understandable to be nervous, but consider what it would feel like to truly trust yourself that you can figure it out. With the power of friends who love you, savvy local experts, and the resources available on the internet, you could totally surprise yourself with how much you’re able to learn and accomplish.
Take the first step to Google something like, “how to start your own business” or “how to take a sabbatical” to get a sense of how it could be done. Once you start to understand what it would take, you might realize that it’s more doable than it seemed.
The goal of a courageous career move is to take a tiny step, even if you’re afraid, that honors your deepest dreams. So commit to a sustainable tiny action that will start to create momentum and affirmation of your desired direction, that's thoughtful of your current circumstances and available energy. As Emilie always says here at Bossed Up, it’s important to make your ambition sustainable, so don’t undervalue tiny baby steps. Every cool, courageous career journey starts with a single step.
Lisa Lewis Miller is the author of Career Clarity: Finally Find Work that Fits Your Values and Your Lifestyle and founder of GetCareerClarity.com where they’ve helped over 500 people make successful career changes.
A primer on getting bossed up.