Starting a Solo Lifestyle Business
Starting a Solo Lifestyle Business
Hello from Tribeca. I spent the first half of the week upstate with my family, enjoying peak foliage and the crisp autumn air. Seeing red, orange and yellow dot the mountains never gets old, and reminds me of playing in piles of leaves as a kid in New England. Transition is in the air.
On Thursday, I hit a milestone that I’m incredibly proud of—I crossed 800 hours of coaching sessions. The path at times has been uncomfortable, confusing, monotonous and lonely, but I’m enjoying the process and who I’m becoming. This reminds me of the quote from George Leonard, the author of Mastery:
“Perhaps we'll never know how far the path can go, how much a human being can truly achieve, until we realize that the ultimate reward is not a gold medal but the path itself.”
Speaking of gold medals, earlier this week I published an essay, “Rethinking Ambition,” that explores how we can rethink and view ambition as something that’s multi-dimensional and personal rather than just tied to work, success and outcomes.
As I’ve written in this newsletter, one of my ambitions in life is to be the father I never had but always wanted—present, patient and committed. Thankfully, I have designed a business and life that provides tremendous balance, so I can be at home when I’m needed and spend ample time with my girls.
I was reflecting on this blessing last week, and posted this tweet:
In the venture-backed startup world, there’s a narrative that goes something like this: lifestyle businesses aren’t ambitious, innovative or impactful, and in order to make a dent in the universe, you must shoot for the moon, raise millions of dollars, employ scores of engineers, and achieve unicorn status. I’ve rejected this notion and chosen a different path because I aspire to balance all of my holistic ambitions, and I believe there are multiple paths to success and fulfillment.
For those of you unfamiliar, a “lifestyle business” is a type of venture that allows you to live the life you want—maybe you could make more money working for someone else, for example, but your lifestyle business gives you the flexibility, freedom and time to enjoy the profit you generate. Sounds pretty awesome, right?
Well, unsurprisingly, the tweet got a bunch of love, and a handful of commenters asked if I had tips or advice based on my experience.
Before I dive in, I’d like to share an important caveat—the point of designing and building a lifestyle business is to create the work-life you want. That’s different for everyone. No person has the same values, ambitions, skills and needs. And no business has the same team, product, customers, brand, and business model. In other words, context matters. What follows is advice I wish I had when I was getting started more than five years ago—though your journey will undoubtedly be unique, I hope some of this helps.
Without further ado, here are the 13 most important tips I have to share on starting a solo lifestyle business!
1. Ask yourself, what does a "lifestyle" mean to me?
According to Dictonary.com, a lifestyle is “the habits, attitudes, tastes, moral standards, economic level that together constitute the mode of living of an individual.”
Start by asking yourself a fundamental question, what’s the lifestyle I desire? What does it look like? What does it include?
What are the building blocks of a great lifestyle? Do you want to fly private, have a big fancy house, work around the clock, become a mega influencer, go to galas, employ a small team, and print money? Or do you want to live in a modest house in the country, save money, pick your kids up from school, take breaks when you want them, and cultivate your craft?
Or something else? Once you know your desired lifestyle you can determine if that truly aligns with your needs and values.
2. Look in the mirror.
Take a step back, explore who you are and how you work. Journaling or voice recorder apps are great for this. Coaching and personality assessments like the Enneagram are also effective for cultivating self-awareness.
Where in my career have I thrived? What do I do well? When am I in my Zone of Genius? What have I struggled with? What activities give me energy? What activities drain me? What’s it like to work alone? What’s it like to work with me? What motivates me intrinsically or extrinsically? What stresses me out? What am I afraid of? How hard am I willing to work to get started?
These questions aren’t meant to make you feel out of depth, but to recognize and name your strengths and weaknesses so you can plan appropriately.
3. Begin with the end in mind.
When we’re mulling a big change, we often think of all the ways that it could go wrong. For example, when I was considering a move to full-time coaching, I told myself a story that I couldn’t make enough money to support a family. Case in point—the financial model I built grossly underestimated where my business is today.
That’s why I suggest envisioning what it would look like if everything went well beyond your wildest dreams. What would you do if you knew you couldn’t fail? How would you feel five years from now if it all worked out? What would be different in your work-life? Dare to dream and see possibilities.
4. Take the long view.
It took about four years from the time I was “coach curious” to operating a sustainable business. That doesn’t mean that you can’t build a business much faster. I know plenty of solopreneurs who have launched and stabilized their business in less than two years.
That said, everything doesn’t have to and won’t happen overnight. If I had tried to quit my job, train to become a coach, and launch a practice all at once, I would have been overwhelmed, especially with a family. I’m glad I took my time, and allowed things to unfold quite naturally.
5. Run experiments.
In Great by Choice, Jim Collins writes “fire bullets, then cannonballs.” This principle suggests that you first fire bullets (low-cost, low-risk experiments) before making a big bet. Once you have data and validation, you can fire a cannonball—go all in. This has been one of my guiding principles.
As my first experiment, I read a coaching book to see if it would resonate. It did. From there, I talked with a few coaches to hear how they got started and what it was like to be a coach.
Once I had this information, I invested and enrolled in a coaching certification program, took on some clients, and eventually charged for my services. A year later and after I got my coaching certification, I had the confidence and data to make the leap—I loved the job, could support my family, and create an awesome lifestyle.
6. Moonlight.
If you have a full-time job but want to explore this path, nights and weekends are an ideal time to learn and experiment.
When I was investing and dipping my toe into coaching, I was lucky because my coaching course took place on the weekends and evenings. Since my schedule was hectic during the day, many of my early clients were open to sessions in the evenings. I was also fortunate to have a life partner who supported me through this exploration during non-work hours.
In the early days, don’t be afraid to view this as a side hustle and maybe a path to incremental income while you get your bearings, run experiments, and determine if this work-life is for you.
7. You are the product.
If you’re a solopreneur, you are the product at least initially. The client is paying you to help them solve a specific problem.
In the early days, focus on the value proposition, the customer experience and the messaging, and then iterate on those as you learn. That’s what really matters. Ask yourself, what is truly core? What really matters? What creates the value for the customer, and how can I deliver that?
Don’t forget there are a number of ways you can turn yourself and knowledge into a product – your time, your knowledge, your learnings, and more. This can take the form of coaching, courses, templates, services, and a range of other self-expressions.
8. Invest in yourself.
Investing your money, time and energy in yourself, your development, and support is essential.
When I was early on the path, I invested heavily in my training and got a coach to accelerate my growth and cultivate new skills. But keep in mind that you don’t even need to spend huge sums of money to begin. YouTube is an educational goldmine, and there are countless podcasts related to solopreneurship. For example, I discovered and devoured several great coaching-related podcasts like Coaches Rising.
This reminds me of something that Jerry Colonna, the CEO of Reboot, shared with me early in my journey, “The Buddha taught that there were 84,000 doorways to the dharma (I kid you not…that’s the number) and the point is to just pick one and walk through. Don’t worry about picking the ‘right one.’ The point is to Start Where You Are.”
9. Engage with your network.
When I enrolled in my first coaching certification program, I shared on social media and emailed my network that I was embarking on a journey and was seeking “practice” clients.
From that initial outreach, a handful of friends and acquaintances were interested to work with me as their coach. I didn’t worry about pricing. I just cared about getting experience, reps, and testimonials. I also shared what I was learning on social media as a way to establish credibility as a trained coach.
This bring to mind my cousin, Marni, who runs Begin With the End, an end-of-life planning service. She recently emailed her network to announce that she was taking on new clients. Guess what? I happened to become one of them. The point is to share what you're working on and learning with your friends, family, supporters and followers.
10. Find a mentor or coach.
Identify someone 2-3 years ahead of you who are willing to share their path, and explain what their days are like.
I was fortunate to have a handful of friends and acquaintances who were coaches, and they were generous with their time, knowledge and resources. I peppered them with questions and soaked up what I heard. What books and resources do you recommend for someone starting out? What attracted you to the profession? What do you wish you knew when you were first starting out? What have been the biggest surprises? What are your days like? How did you build your practice and get your first customers? What do you love? What do you struggle with?
Remember, that mentors come in all different mediums in addition to IRL. Many of my mentors I haven’t met and some aren’t living, but I consume and learn their wisdom in books, videos and podcasts.
11. Know thy customer.
Select an audience or an ideal customer that you know well or are passionate about.
At first, you might not know for sure, but you might have a hunch. It’s ok if you don’t have all the answers, especially in the early days. Run some experiments. Get out and interview prospective customers. What are their problems? How are they currently solving them? What motivates them? What do they think and feel about what you have to offer? How much are they willing to pay?
After some initial exploration and hunches, you might not be ready to fully commit to one client type. That’s also ok. Early on, I began working with early-stage founders, VCs and leaders in transition. This is the world I was immersed in, so it made sense, but I wasn't sure if one type of client would emerge as the primary. It turned out that I could uniquely serve all three given my experience. I still coach those three personas, though I'm presently feeling called to help successful builders and creators find their second calling in life.
That's all to say knowing who you serve is essential, so you can tailor your communication and deliver a product that capitalizes on its promise.
12. Engage online.
The biggest investment I made in my career was joining Twitter in the early days and consistently engaging with that community. Some of my best friends and biggest supporters have been formed on that platform. It has become a way for me to share myself and my journey with the world, exchange thoughts and ideas, and even meet prospective customers.
That said, there are a variety of online communities beyond Twitter such as YouTube, Instagram, Substack, TikTok, Reddit, and more. Ask yourself, which medium feels most native to me? How do I like to express myself and engage? Where do I think my people are hanging out online? Who can I learn from?
Engaging online to learn and collaborate is one of the most effective ways to grow your brand and business. Again, take the long view on this, because it doesn’t happen overnight. If you’re not already online and active, begin with the mindset you’re there to learn, comment on posts that resonate, and share where you are in your process and journey. You’d be surprised how quickly you can build a small community to support you on your path if you're willing to engage. There are some amazing and talented people to follow who are on this journey and generously share a wealth of knowledge. My friend Justin Welsh is a must follow for anyone wanting to become a solopreneur.
13. Have fun.
Finally, bring levity to the process, smile, dance, and laugh a little. All of these go a long way when the doubts and setbacks occur. A positive attitude can take you far.
Designing and creating a solo lifestyle business has been one of the best decisions of my life. I get to set my own hours. I don’t have to manage any employees. I own my days. I take my daughter to school and write in the mornings. I take off time when I want to. I earn enough income to support my family and invest in our future. I don’t report to anyone other than my clients. I'm not going to lie, I can't believe I've been able to create this for myself and my family. But if I can do it, so can many of you.
At the end of the day, the business is on my shoulders, and I have to perform. That motivates and energizes me, but this might not be for everyone. Thankfully, I took my time, got help, ran experiments, and invested in myself, so I knew this was the right path for me when I was finally ready to burn the boats and go all in.
Are you on the solopreneur path? If so, I'd love to hear about your journey so far.
🌱 Seeds of Change
✨
Here are five things I’ve been pondering and exploring over the past few weeks. If any resonate, please feel free to forward along to friends.
🌌 Cosmic Insignificance Therapy
Earlier this year, I devoured the excellent and deeply thought provoking 4,000 Weeks: Time Management for Mortals by Oliver Burkeman. It’s an exploration of our relationship with time, our finitude, desire for productivity, fixation on accomplishment, and more. A mind bending concept from the book is “Cosmic Insignificance Therapy.” It goes something like this: from a cosmic perspective where time extends infinitely into the past and into the future, our lives are quite insignificant. But instead of falling into despair and embracing nihilism when we sit with this truth, Burkeman encourages us to embrace our “cosmic insignificance” because it can help us take our lives less seriously, travel the path we long for but are afraid to walk, and live life on our own terms. Here’s a short talk from Burkeman on our cosmic insignificance in the The Waking Up App (12 minutes).
✨Our Search for Meaning
Man’s Search for Meaning by Viktor Frankl is my favorite book of all time. I’ve read it a half dozen times and gifted it more times than I can count. That’s why I was thrilled when my friend Jonny Miller from Curious Humans shared this rare 1972 talk from Frankl where he passionately emphasizes why we need to find “the spark” of meaning in our lives. Watch on YouTube (4 minutes)
🎭 Character Invention
I’m a huge fan of leveraging persona and parts work for my clients and my own development. That’s why my interest was piqued when I discovered this helpful and actionable Twitter thread from entrepreneur Matt Shnuck on how to use a technique called “character invention” to overcome imposter syndrome. Schunck explains, “The technique rooted in drama therapy and Neuro-Linguistic Programming (NLP) is to invent a character who can do what feels scary to you. Then, the ‘character’ performs outside your comfort zone.” Matt illustrates this by highlighting Sasha Fierce, a fearless stage persona that Beyonce created to overcome her fear of performing. I just love this concept. In fact, I’ve been experimenting with a few coaching and speaking personas to help me overcome some long-held self-limiting beliefs. I can sense a future essay exploring this idea.
👩🏻🎨 Designing Your Life: Creating Odyssey Plans
Several years ago, I read the bestseller Designing Your Life by Stanford D-School Professors Bill Burnett and Dave Evans, and worked through all the exercises in the book. In fact, it was instrumental when I was deciding to leave venture capital in favor of coaching. A few weeks ago, I revisited this classic and worked through the “Odyssey Plan” exercise to get clarity on a few paths I’m contemplating, and to use with several of my existing clients. According to Burnett, there are six transitions in a modern adult life, and at each of these transitions it’s helpful to ask, what’s next? Odyssey Planning is a process to brainstorm and explore three alternative paths for how your life might evolve over the next five to ten years. When I was revisiting the process a few weeks ago, I discovered an awesome video series where Burnett walks through the entire process. If you’re at the beginning or middle of a transition, I can’t recommend this enough. Watch on YouTube (30 minutes)
🛞 Watching The Wheels
I love the Beatles, and I especially love the music that emerged from Paul, John, George and Ringo after they broke up. Wings. All Things Must Pass. Imagine. The Traveling Wilburys. Pure creative genius! One of my favorite songs ever since I was young has been “Watching The Wheels” by Lennon. He wrote that song in response to criticism he received for choosing to get out of the music business and be a dad and husband for a while. I revisited this song over the summer, and it spoke to me in a way it hadn’t before. A few days later, I stumbled upon the original music video on YouTube, which is filled with rare footage of John being a father and family man. When I listen to it now, the lyrics inspire me to carve my own path forward and live in the present. May they do the same for you:
People say I'm crazy
Doing what I'm doing
Well, they give me all kinds of warnings
To save me from ruin
When I say that I'm okay, well they look at me kinda strange
"Surely, you're not happy now, you no longer play the game"
People say I'm lazy
Dreaming my life away
Well they give me all kinds of advice
Designed to enlighten me
When I tell them that I'm doing fine watching shadows on the wall
"Don't you miss the big time boy, you're no longer on the ball?"
I'm just sitting here watching the wheels go round and round
I really love to watch them roll
No longer riding on the merry-go-round
I just had to let it go
Ah, people asking questions
Lost in confusion
Well, I tell them there's no problem
Only solutions
Well, they shake their heads and they look at me, as if I've lost my mind
I tell them there's no hurry, I'm just sitting here doing time
I'm just sitting here watching the wheels go round and round
I really love to watch them roll
No longer riding on the merry-go-round
I just had to let it go
I just had to let it go
I just had to let it go