becoming your own boss: how to take the leap and land on your feet
From buttoned-up to being myself
I was hovering somewhere between Austin and San Francisco when the idea washed over me like a warm bath, clearing away the miserable fretting that had been sending my body and mind into a state of constriction for months:
What if I could quit my job but keep the best parts?
The job I’d had for 4 years no longer felt like a fit, but some of the work really worked for me. I grabbed my notebook and started sketching as the roar of the airplane cheered me on from all sides. What would it actually look like to quit my job and keep the best parts?
First, I examined all the things I spent my time doing at work. When I boiled down a long list of responsibilities, projects and tasks, there were 3 things that truly energized me. And I really loved doing those things. I jotted them down on their own piece of paper, took a long, hard look at the shortlist, and smiled. When I dared myself to imagine the possibility of living my life doing just those 3 things, a colorful burst of hope bloomed in my heart like a bright pink peony. Could I really just do those things? My shoulders lowered one inch further from my ears and my mouth turned one dial upwards from the uncharacteristic frown I’d come to know so well in recent months.
Within a matter of weeks, I began the process of leaving my job. I would go on to maintain a strong relationship with my employer, convert them into my biggest client, and explore new opportunities based on my truest values and passions. Now, 2 years later, I’ve built a fruitful business doing just the 3 things I identified as my north star when I took the leap: executive coaching, experience design and facilitation.
Stories of “failure” are wonderful teachers — and I have many of those! — but the ideas I offer here emerged from lessons I’ve learned based on what went well as I left the corporate world to become my own boss. Taking a leap may or may not be the right decision for you at this time based on all the factors that are unique to you and your life. Whatever the case may be, I hope these lessons will be helpful for you as you navigate your own path in your own context.
1. Know When It’s Time to Let Go
“And the day came when the risk to remain tight in a bud was more painful than the risk it took to blossom.” — Anaïs Nin
It’s a big decision to leave your job. It stirs up all our biggest fears about scarcity and identity. How will I feed myself and my family if I leave the security of this job? Who will I be in the world if I leave this job? What will become of the important relationships I’ve built?
As a leader in the realm of people operations, one of my responsibilities was tracking employee engagement. Once I admitted to myself that I had become my own worst nightmare — a (gasp!) “disengaged employee” — I knew that if something didn’t change, the negative energy I was feeling would create a ripple effect and I would become a source of toxicity for the culture of my organization. I’d seen this tape before and coached many people who had worn these very shoes. I had three options: change my mindset, change my circumstances, or change both.
I decided on door number 3. It was time for me to both shift my attitude back above the line and leave the nest of an organization that had been such a wonderful home for me, until it simply no longer felt like a fit.
We all have to ride out tough times, and there will be tough times with every job, including when you work for yourself. But when you reach a point of burnout, depletion, misalignment, or resentment that feels more like a new default state than a rough patch, that’s when you know that for your own sake and for the people around you, it’s time to change your mindset and perhaps time to let go.
2. Tap Into Your Curiosity
“How we spend our days is, of course, how we spend our lives. What we do with this hour, and that one, is what we are doing.” — Annie Dillard
At the root of my disengagement was the fact that the demands of my job had become increasingly misaligned with my skills, passions, and interests. I was spending way more time doing things that drained me than things that energized me, but that’s what the company needed, so month after month, I pushed myself to do what was needed… until I felt depleted. It’s easy to give attention to what’s not working since we humans are wired for negativity bias. Soooo, how do you flip that switch?
My friend Scott Shigeoka, who found success leaving his job to do what he loves doing, has great advice: start by tapping into your curiosity. “When you’re beginning a transitional period of your life, try leading with questions instead of answers,” Scott says. We often put pressure on ourselves to get clear about our goals and direction, but this can put unnecessary pressure on us to be in a state of knowing. What really might serve you, Scott says, is to be in a state of exploration and discovery instead. Scott recommends doing “disco” calls (‘disco’ is short for discovery) where you ask questions and engage in dialogue with others to explore what gives you energy, and what sucks it out of you (your ‘energy vampires’). “If you’re not feeling social, you can also get curious by journaling with a pen and a paper,” Scott says. “I’ve also developed a practice called BodyJournaling which involves reflecting with movement — just close your eyes, start moving, and think about what energizes you. Then see what emerges!”
Here’s another exercise you can do to get curious about what drains versus energizes you, which I learned from my friends and mentors Frances Fujii and Tom Voccola at CEO2. In the right-side quadrants, explore the work-related activities that feel like “energy vampires”: on the bottom write down the things that you’re not so good at, and on the top the things you can do just fine but drain you in the end. In the left-side quadrants, explore what gives you energy: on the top left write down things you’re excellent at that give you energy, and on the bottom the things you’re best at that give you so much energy you could do them all day then keep doing them! These are your Unique Abilities. For example, hosting is one of my unique abilities, and facilitation is how that plays out in my professional life.
Passion Meter Exercise
This Passion Meter, developed by my friends and mentors Frances Fujii and Tom Voccola at CEO2, is another exercise you can do to explore what generates versus zaps your energy. Write down any work-related or personal life activities that match each column to get a better sense of what kinds of things you’d like to spend more or less time doing. You may even discover things you love doing in your personal life that you can apply to your work life. For example, I love hosting — dinner parties, gatherings, events, you name it — and facilitation is how that plays out in my professional life.
Instructions: Explore your energy generators versus energy vampires with this simple tool
If how we spend our days is how we spend our lives, as Annie Dillard says, don’t you want to spend your days doing things that energize you? That’s what it means to be an “engaged employee,” whether you work for yourself or someone else!
3. Own the Value of Your Work
“We can’t ask people to give to us something that we do not believe we’re worthy of receiving.” — Brené Brown
As my friend Colette Kessler says, it’s important to recognize that the circumstances we are born into may have a large impact on our risk tolerance. That said, whether you’re striking out on your own as a consultant, an entrepreneur, an artist, or any other role that requires you to determine the value of the products and/or services you provide, the extent to which you believe in and advocate for the value of your work is critical. As our own bosses, we must believe in, root for, and represent ourselves just as we’d want the best boss in the world to do, and for the value of our work to be reflected in part through our compensation.
In discussing this topic with Colette, who launched her own business, The Impact Studio, 5 years ago to partner with audacious companies and creatives ready to make a positive impact, we came up with three main things to consider:
Understand your baseline
How much is enough? What’s the dollar amount you need in order to live and exist in a way that fulfills your basic needs and desires? Identify how much is enough, and set that amount as your baseline. This establishes a specific monthly and/or yearly goal from which you can choose to take on more work and increase your earnings, or reach and be satisfied. Ideally, your baseline enables you to make smart decisions about when to say yes or no to new opportunities, depending on how much or how little you want to work at any given time.
Information is your friend
When it comes to pricing your offerings, start by doing research to get informed so you can give yourself spectrums and stakes. Turn to the internet and have live conversations — what are people being paid to do what you’re doing? What are large companies that offer similar products/services charging to do the kind of work you’re doing? What is the high end, and the low end? How much elasticity does a particular company or the marketplace have to pay for what you can offer? Prepare yourself for some making-it-up and throwing darts at the board, but price your offerings towards the high end if you feel confident in the quality of your work and experience. This is how you establish yourself and build confidence and competence.
Price for the bigger picture
If you’re becoming your own boss, you’re likely stepping into an entirely different model of employment than that of a salaried employee. Salary vs services is like apples and oranges, so rather than taking your last salary and dividing it by the number of hours you work, or billing by the hour, we recommend pricing your work based on the total value of a project or establishing a scope of work to be paid through a recurring retainer fee for ongoing clients. When you begin with the end in mind and use the ultimate value of a project as your compensation compass, the hours you put in become inputs to determine overall pricing as opposed to the price itself. This is advantageous for both parties so that rather than getting stuck in a cycle of nickel-and-diming, all parties are freed up to focus on collaborating to achieve a shared goal.
4. Choose Wisely Who You Work With
“Choose people who lift you up.” — Michelle Obama
One of the best things about becoming your own boss is that you’re the one who decides who you work with and who you don’t. This is an opportunity to be really honest with yourself about the type of energy you want to engage with in your life.
For me, that process started by asking myself if I wanted to continue working with my former employer, which I unquestionably did, seeing that I still cared deeply for the people, projects, and initiatives I’d poured my heart into as a full-time employee. As I began spreading my wings and working with new clients and collaborators, some projects went smoothly and resulted in exciting new relationships, while others were awkward and off putting.
Similar to running a hiring process, I’ve learned that there are thoughtful ways to determine whether or not you think a new client or collaborator would be a good fit. Here’s a set of intuition-based questions you might ask yourself when considering who you want to work with.
Partnership Discovery Questions
When I leave conversations with this person or organization, do I feel more drained/overwhelmed or energized/excited?
What are my values, vision and/or mission and how do they align or misalign with what I know or perceive theirs to be?
On a scale of 1–10 with 10 being awesome, how do I feel when I’m engaging with this person or organization?
We do NOT have to work with everyone who shows up at our doorstep. Saying no is an important skill to practice, and there is power in being clear about who you are and what does or does not resonate with you. By saying no to people and projects that don’t feel like a fit, not only do we open up more opportunities for the right people and projects to materialize; we find ourselves living with integrity.
5. Make Space for What Matters Most
“The key is not to prioritize what’s on your schedule, but to schedule your priorities.” — Stephen R. Covey
When you think of the word “time” in a work context, what comes up for you? Historically, I would have told you that I feel a constriction in my throat, my heart speeds up a little, and my breath shallows. There’s a sense of urgency, scarcity and intensity — like there’s too much to do and not enough time. As my own boss, I’m in the process of healing and reclaiming my relationship with time. It started with the transitional period when I took the leap, and has worked its way into the design of my day to day life.
Let’s consider your ideal workday during a new chapter where you’re your own boss. What does it look like to truly prioritize the things that matter most to you and ensure their importance is reflected in the way you structure your time? For me, friendship, nature, exercise and creative expression are crucial to my happiness, so I place phone calls with friends, walks in nature and creative writing blocks as anchors in my days and schedule work around those activities. What are the crucial elements to your ideal workday?
Perfect Workday Exercise
Picture your ideal workday. From the moment you wake up, through breakfast, late morning, lunchtime, mid-day, evening and all the way to bedtime. What activities are you engaging in? What is the pace? How much time and space do you have to do what? Set a timer for 3 minutes, put on a peaceful song, close your eyes, and let your imagination go. Don’t hold back. Write down what you discover.
There are amazing tools out there to help you structure your time with intentionality. I recommend holistic planners like the Monk Manual (my current obsession) or the Passion Planner.
Stick the Landing: Embrace the Experimentation Process
“There is no right or wrong, only thinking makes it so.” — Shakespeare
No matter which way you leap, you will be met with situations and experiences you’ve never faced before. My mother taught me that “there are no mistakes, only lessons.” I love this ethos, because it gives me permission to try new things without letting too much fear get in the way.
Everything is an experiment! This mindset helps us approach all the unknowns we’ll ever face with curiosity and fascination. What can we discover out there in the world and inside ourselves as we break new ground in our lives?
For all the leaps we’ll ever take, I hope we can remember one simple idea. There is no right and wrong, there is only right and left. Whatever direction you take will lead you to your next phase of growth and learning and that, my friend, is a most worthy cause.