One of my favorite sections of the paper is the one-page Q&A feature from the Sunday Magazine. They always feature interesting people, and the conversational questions and answers provide an engaging snapshot of what is important to each person, what they’re working on and what keeps them up at night. In that spirit, I’ve provided short replies to anything you could want to know.
Q: Everyone’s definition of success is different. What’s yours?
Living a day-to-day life that brings me a sense of fulfillment, health, and peace of mind. Working with ease. That doesn’t mean the work always feels easy, but that I continuously find ways to reduce stress, ask for help, build better systems — all in service of doing my best, most creative work. Success to me is about living an abundant life, but so much less about the dollars in the bank account than I once thought. Sure, having money and income are nice markers of success, but they are nowhere near everything. Much more important to me is that I have integrity, joy, and excitement about what I am working on and the way that I am working on it. —Going Pro Magazine
Q: Let’s get down to business brass tacks. When you say “solopreneur” what does that really mean?
I don’t really consider myself a full-blown entrepreneur looking for funding or to grow a company to dozens of people. I am running a (mostly) solo location-independent lifestyle business that I prefer to keep nimble and suited to my own personal needs.
Q: So where, exactly, does your money come from?
In order from most consistent (and highest revenue) to least:
The majority of my income comes from 1:1 micro-business coaching (typically related to helping someone start or grow a book, blog, or business) and career coaching (navigating a big transition).
Next up is income from online courses which comes in big chunks 2-3 times per year (currently the main sources are Build Your Business and Make Sh*t Happen).
Tied for second is speaking engagements — but those are sporadic and mostly reactive (they find me). About half are paid keynotes, and half are conferences that pay a small honorarium. I also do some corporate training.
After that, small bits and pieces of income come from affiliate sales, book royalties and teaching yoga. Though all three of those usually end up at pennies on the hour for time spent 🙂
Q: What do you think it really takes to be successful in business?
Building “entrepreneurial resilience” (a term coined by my friend Alex) is like building a muscle; it takes practice. I believe that becoming a solopreneur or small-business owner is one of the biggest personal growth journeys a person can embark upon. It will call up all your fears, weaknesses, insecurities, and challenges. But it will also bring out the best in you — your innate widsom, leadership ability, creativity. Being successful requires being nimble, learning to ride the waves of income and uncertainty, and even your own big life changes that may be happening in parallel.
The old adages ring true: get comfortable being uncomfortable, and the only certainty is uncertainty. As a solopreneur, especially in the beginning, you’ve got to get comfortable not knowing exactly where every dollar will come from. Work comes in, work gets canceled. You sell things and it works; you sell things and they flop. Developing semi-passive income streams takes time, and there’s nothing passive about the process. One night I went to bed with a knot in my stomach about how I’d pay my credit card bills. The next day, in one hour, I had sold $5K of business. The next week, it was put on hold. You’ve got to get comfortable (or as close to comfortable as you can) riding that wave without getting discouraged or freaking out, but also learn from it at the same time about what you can do differently moving forward.
Making the Leap
Q: Entrepreneurship is largely a mindset game. What mindset shifts did you have to make in order to play bigger?
Two things: ditch perfectionism and draw boundaries and learn to say no. Perfectionism is a killer because it means that nothing gets shipped. If you take your products, pricing, writing, marketing, etc. too seriously, nothing will get done. I started having much more fun with my business when I took the pressure of to be perfect, and started adopting the more agile “launch and iterate” model that I learned while working at Google. The culture there was so dynamic that the entire goal was to ship even if things were imperfect in order to get feedback early on in the development process.
Drawing boundaries and saying no is also incredibly important as an entrepreneur, particularly if you are looking to play bigger than you already too. The adage “what got you here won’t get you there” often rings true — if you say yes to everyone and everything (including friends and family, or clients you know aren’t the exact right fit), you will be limiting your ability to truly take your business to the next level. As John C. Maxwell said, “Learn to say no to the good so you can say yes to the great.” —Going Pro Magazine
Q: Were you ever scared to really put yourself out there and take a stand for what you believe? How did you overcome it?
Absolutely! I knew that despite the fear I had about leaving the comfort of my full-time job, the regret of not going for it and accumulated effects of sitting idle were far worse. And by idle, I mean not doing anything about the fact that I was completely burning myself out. I was working full-time and writing my blog and book on nights and weekends. There was no time for rest or play, and I knew this would not be sustainable for much longer. My courage did not come overnight, but rather things got to the point where the indecision was tearing me apart and I knew that it was now or never to give it a shot. I had six months of savings, and for the first time, I was willing to spend every penny of it to know that I had at least tried to launch my own business. I am very grateful to say that two years later, I’m doing just fine financially — and happier and healthier than I’ve ever been. —Going Pro Magazine
Q: How did you get into doing this work, and what do you like best about your work?
I absolutely love working with people on what is most important in their life and on taking action to make meaningful changes — primarily in the career or small-business space. I completed my coach training in 2008 and since realized that my “sweet spot” is what I like to call activation coaching — helping people dig in and start something or grow something — I have a bias toward visioning, planning, then taking action. I am the coach that sends you Google docs, spreadsheets, book recommendations, connections and plenty of homework — in short, I make you work! But that’s when coaching becomes incredibly rewarding — when I can help people achieve things they never thought possible on their own.
Q: It’s no surprise that startup growth is often where entrepreneurs struggle most. What advice do you have for scaling a business?
Start slowly and trust your gut. Don’t take clients, contract work or agree to events that feel “shackles on,” to borrow a term from author and life coach, Martha Beck. They will just end up draining your energy and are ultimately not worth the money. As the saying by John Maxwell goes, “Learn to say no to the good so that you can say yes to the great.”
Q: What popular entrepreneurial advice do you disagree with? What advice would you give to fellow entrepreneurs instead?
I disagree with the notion that we always have to be going, going, going–hustling, working around the clock and not sleeping. I think that’s an old school approach. To run your business—especially a creative one—in an intuitive, heart-centered way, you have to allow yourself some time and space for reflection. Sometimes that might be a week, but in some cases it will be a year. Let go of the need to be selling and creating 24/7–your customers will be much happier and more engaged if they trust that what you are producing comes from a grounded, thoughtful place.
Q: What are the three key elements you’d attribute to starting and running a successful business?
1. Focus on your vision first.
I once had a coach tell me not to get bogged down by the “tyranny of the hows.” I bring big ideas to life by focusing on the vision first—getting super clear on what smashing success looks like and very specific about how I will feel once the idea comes to fruition. Creating a compelling vision gives me the ammo and excitement to move forward, and the “hows” often naturally fall into place from there — at least when something is meant to be. And if it isn’t? It’s all learning fodder, baby. Get up, dust off and keep going.
2. Work on your own schedule.
My career used to be about doing things I “should” be doing to please my manager, parents, society and even blog readers. Since I’ve been on my own, the most important thing I have learned is to work on my own schedule, my own projects and to set up my time in a way that truly honors myself and my health. I still love big projects and tackling meaty ideas (which require their fair share of hard work), but I put way less pressure on myself to be successful by external measures and I put much more emphasis on feeling happy and healthy above the work achievements. I may take longer to launch a new product, but I’m working at a pace and lifestyle that really works for me. I often repeat the mantra, “Let it be easy, let it be fun.” If something I’m doing isn’t, I know it’s time to consider a different approach.
3. Take care of your health!
For the first month of running my own business, every day was a roller coaster. Some days I would wake up super productive, and others I’d feel exhausted or worse–just plain lazy. I wasn’t running my business, my business was running me. And as 100% of the company, the opportunity costs of operating at half-mast were extremely high. So I started exercising every day and even completed a 21-day cleanse. I felt clear-headed, creative, confident, energized, productive and happy. I was getting more done in one week than I had completed in one month. I was no longer experiencing crazy mood swings or unproductive days. I started sleeping like a rock. I was in a great mood, glowing and energetic at conferences and razor sharp during my coaching and speaking engagements. I was on a roll and I stayed there.
I used to scoff at the countless magazines that preach healthy eating and exercise until I experienced, firsthand, the insanely powerful impact it had on my business’s bottom line–not to mention my actual bottom, which now fits nicely back into my best jeans.
—From my Lifehack guest post: The best decision you can make for your business — that has nothing to do with money
My Typical Day
Q: What does your typical day look like?
I work with coaching clients on Mondays and Tuesdays, then usually take the rest of the days to do behind-the-scenes work — writing, course building or facilitation, and planning what’s next. I am more likely to take Wednesday and Friday off than the weekends. In fact — weekends and holidays are my favorite time to work; less input from the Internet (emails and social media), more creative output from me. I mostly answer emails in big chunks — usually on Sundays.
I try to take a yoga or pilates class almost every day, and I walk everywhere whenever possible. Being your own boss can sometimes feel like a 24-hour a day gig, so exercise (and fresh air!) really helps remind me to step away from the computer and interact with other humans in person (crazy, right?). Exercise also helps activate my brain for the day (and happy chemicals) and gives me time to think through what my biggest priorities are. When it’s in the evening, it’s the perfect way to let of steam and let the business stuff go for a bit. My ideal night out is a long, delightful multi-course dinner with friends. —IdeaMensch Interview
Q: As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?
Even if you only have five minutes, make a point to sit with your eyes closed and breathe. Better still — use the Insight Timer app and set a goal to do 20 minutes, at least three times a week. It’s like building a muscle — it will get easier over time, and you will be amazed at the clarity and creative problem-solving it brings in life and business. Insight Timer will help you build the habit by keeping a log of your sessions, as well as an optional “journal” prompt when you finish to collect insights and ideas.
—From Tech Cocktail: 27 Simple Health Tips From Entrepreneurs, For Entrepreneurs
Q: If you weren’t working on your coaching, speaking and blogging, what would you be doing?
I really love having yoga teaching in the mix. It continues to be one of my biggest challenges (instructing every breath and movement while demonstrating, really seeing the class, and adjusting) — and it’s such a great balance to all the “heady” computer work I do most of the time. I also love the idea of sharing my “medicine” with other entrepreneurs and doing it in a way that’s fun, non-intimidating and helps connect awesome people with each other (another passion of mine).
Q: Where’s the coolest spot you’ve ever taught or practiced yoga?
I taught the final class I needed for certification in a cenote (cave) in a Mayan jungle at a gorgeous retreat center called Taninah just outside of Playa del Carmen. Magical. Other favorite spots: teaching my Vision & Vinyasa workshop at Wild Rose Yoga in Chiang Mai, Thailand.
Q: What are 10 online tools you use every day?
- Workflowy: for staying on top of tasks on a project-by-project basis, and TeuxDeux for organizing a few days at a time.
- Evernote: Can’t live without it! It helps me track ideas and tasks across all my gadgets. I have a notebook called “Watch/Do/Read” that serves as a nice bucket for things I want to come back to later. I also use Instapaper for this purpose (particularly for longer articles).
- Feedly is what I use for my go-to feed reader, which also syncs with Instapaper..
- Google Docs: I’ve created lots of templates over the years to organize every area of my life and work. Check them out and grab any that seem helpful to you in the Business Ninja Toolkit!
- Droplr: Awesome for easily sending screenshots to people; anything from music playlists to image grabs and Bit.ly for customizing short-links that I send to others, provides metrics and tracking.
- Spotify: Listen to custom playlists or spotify radio, share with friends. Music always keeps me motivated!
On the Creative Process
Q: What’s one trend that really excites you?
Because of the Internet we have more potential to create and drive our career than we ever have before. One of my keynote speeches is, “The Ladder is Out: Career in the Age of the App,” which is all about ditching the linear template mindset and moving toward a model where we each take full responsibility for the “apps” (skills, experiences, hobbies, job experiences, side hustles) that make up our careers. You are the creative director of your life — you decide what’s next, on your own terms. That’s a liberating thought to me.
Q: What advice do you have for trying to hone in on our purpose in life?
Start with a big, sprawling creative exploration — don’t try to hone in on just one thing off the bat. Do a mind-map or make a list of all the things that bring you joy and why, and what alternate careers you would have if money or time were not an issue. Once you’ve been at this and really explored every nook and cranny, then you can start to look for themes and areas where you might want to focus your attention. Beyond that, what are your marketable skills? Look for the intersection of three things: when you feel most in the zone, your technical skills and knowledge, and what people will pay you for (market need). Finally, nothing is permanent! Explore and experiment with listening to your gut until you land on something that feels really exciting.
Q: What’s a big goal you have that we probably don’t know about that scares the bejeezus out of you?
You know what’s funny? I run a course on goals that I love with my whole heart AND after I knocked off some of my biggest ones, I found myself in a goal-free state. I have things like traveling and living abroad, but mostly even just maintaining my own business, health, lifestyle and relationships, has me overwhelmed by gratitude and good fortune.
Q: You can’t wiggle your way out of this! Give us something.
Okay fine! I want to learn how to do a press-up handstand in yoga (seriously feels like a lifetime effort), live abroad for at least three months while still running my business (I came close by living in Bali and Thailand for two months earlier this year), and to go on an African safari.
Q: How do you overcome doubts when “Making Sh*t Happen”?
Part of it is realizing and accepting that you WILL have down days, hit a big dip, feel self-doubt, and want to quit — and probably all of those things many more than once throughout a big project or journey! Accepting that these are natural and not some great personal shortcoming helps me recognize them, acknowledge them, and move through them.
Q: What advice do you have for others tackling a seemingly overwhelming idea?
I like to tell people to “live big and start small.” Even the biggest ideas have a first step you can take, even when you can’t see the full path. Start there, then the next step will reveal itself, and the next until you eventually have a snowball of momentum. At that point you have already achieved intrinsic success for just for being on the playing field.
Stand tall and shine your light in the world. When something is right, the universe will roll out the red carpet for you; lean in and let serendipity help do the work (balanced with intentional effort).
The Personal Stuff
Q: Who is one of your personal heros?
I am fortunate to have many heros, but the one that stands out is Susan Biali, one of my mentors and now good friends. She has been an inspiration to me since day one. She’s an MD turned flamenco-dancing life coach, author and speaker. She is so poised, wise and generous with her time. She’s been incredibly supportive of me, even before I had any momentum from my blog. Susan has been with me at every step of my process — getting the book deal, learning the art of being a professional speaker and learning how to stay healthy, happy and sane in the midst of it all. She has demonstrated what’s possible for me in this field and has done it with such grace and courage. —IdeaMensch Interview
Q: What’s on your nightstand?
Besides the lamp . . .
- A SmartWater bottle (this is literally glued to my hand throughout the day)
- My iPad Mini (practically a third hand at this point)
- Earplugs (NYC gets crazy loud!)
- Coconut lip butter
- My journal (a trusty five-star notebook)
- I don’t have a TV, so on some nights I’m also taking my laptop to bed for a Hulu show or two
Q: What keeps you awake at night?
If I’m tossing and turning, it’s either problem-solving or brainstorming around a big work-related idea or it’s a personal issue, usually around relationships — platonic and romantic. Did I say or do the right thing? Could I have done anything differently? What am I worrying about and what can I do about it? I am prone to spinning if I don’t watch myself…hence the yoga and exercise to keep me sane!
Q: What’s on your playlist?
I make a mix for every season (been doing that since I was in high school), so the playlist tends to change with the weather. My long-time stand-bys are Adele, Bon Iver and Ben Howard. When I’m feeling upbeat or in the zone, I listen to anything that gets me dancing, singing or walking through the streets of New York City as though I’m the star of my own movie. Ridiculous, I know.
Q: When was the last time you laughed out loud? What caused it?
I told my roommate that I had achieved the equivalence of a solar eclipse with shooting stars and unicorns bounding through the sky: the mythical Inbox Zero that I’m lucky to reach once every 2 years. We had a good chuckle picturing all the fanfare — until the next one came in 2 minutes later.
Q: Which guilty-pleasure website do you visit every day?
I visit Dlisted for mind-numbing but snarkily-awesome celebrity gossip. It’s my guilty pleasure…I can’t help myself!
Q: Speaking of which, tell us a secret.
I still sleep with a teddy bear . . . the same one I’ve had since I was 6 years old. He somehow always ends up in the coveted inner spoon position.
Books & Quotes
Q: You’re a self-proclaimed book worm and “book doctor.” What does that mean?
Ever since I was a kid, books have been the source of so much learning, inspiration, comfort, growth, solace and mentorship-from-afar — and the really good ones have changed my life.
On being a book doctor: you come to me with what ails you, and I write you a prescription of 3-4 must-reads. I’ve read over 250 non-fiction books (mostly in the categories of non-fiction, health, business and personal development), so chances are, I’ve got the perfect one for you. My no-fail book recommendations are Finding Your Own North Star by Martha Beck, and The Big Leap by Gay Hendricks.
Q: What’s your favorite book? Why?
A few favorites: Finding Your Own North Star (Martha Beck), The Big Leap (Gay Hendricks), Escape from Cubicle Nation (Pamela Slim), When Things Fall Apart (Pema Chodron), Maximum Achievement (Brian Tracy), Tao de Ching, Living with Joy, and Resonate (Nancy Duarte).
My all-time favorite book is The Catcher in the Rye. A quote that reminds me why I love to read and write, especially when I feel blocked:
“Among other things, you’ll find that you’re not the first person who was ever confused and frightened and even sickened by human behavior. You’re by no means alone on that score, you’ll be excited and stimulated to know. Many, many men have been just as troubled morally and spiritually as you are right now. Happily, some of them kept records of their troubles. You’ll learn from them—if you want to. Just as someday, if you have something to offer, someone will learn something from you. It’s a beautiful reciprocal arrangement. And it isn’t education. It’s history. It’s poetry.”
―J.D. Salinger, The Catcher in the Rye
Q: You’re a quote junkie. What words of wisdom do you find most valuable?
I love this quote from the Dalai Lama, as it perfectly captures what I aim for within each day.
“Every day, think as you wake up, today I am fortunate to be alive, I have a precious human life, I am not going to waste it. I am going to use all my energies to develop myself, to expand my heart out to others; to achieve enlightenment for the benefit of all beings. I am going to have kind thoughts towards others, I am not going to get angry or think badly about others. I am going to benefit others as much as I can.”
—Dalai Lama XIV
And another all-time favorite quote from Rainer Maria Rilke that reminds us to love our challenges:
“Perhaps all the dragons of our lives are princesses, who are only waiting to see us once beautiful and brave. Perhaps everything terrible is in its deepest being something helpless that wants help from us. So you must not be frightened, dear Mr. Kappus, if a sadness rises up before you larger than any you have ever seen; if a restiveness, like light and cloud-shadows, passes over your hands and over all you do. You must think that something is happening with you, that life has not forgotten you, that it holds you in its hand; it will not let you fall.”
—Rainer Maria Rilke
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