Starving to Six: 6 lessons I learned on my journey from 'starving artist'​ to six-figure entrepreneur


Let me paint a picture. I'm an artist, after all.

I'd recently turned thirty, and was officially a decade into my career as an avant-garde musician. And my career, as far as young avant-garde careers go, was in a good place. Mine was the kind of career that brought me around the world, afforded me my own ensemble, and had me playing at places like Carnegie Hall. (In fact, my band's last performance was at Carnegie Hall - a concert that I'd largely bootstrapped. But that's a story for a different time.)

So when I got *the* text message - the one that would effectively change my entire life - I'd love to be able to tell you that I was backstage before a big performance, or holed up in a practice room working on my magnum opus. But the reality is far less glamorous.

I was in the middle of a particularly difficult odd job. I was the queen of odd jobs throughout my twenties - teaching music for cash, transcribing handwritten scores into notation software for master composers, gigging, administrative assisting, temping... the list goes on. I worked constantly and exhaustively. Because the thing that they don't tell you in music school is that many musicians, no matter how successful, can never afford to retire. In fact, you can be good enough to put on a concert featuring just you and your band to a well-attended audience at Carnegie Hall, and be broke.

And I was broke. I was every cliche in the book: writing music into the night because I had no time during the day due to aforementioned odd jobs; eating cost-effective-yet-questionable food from packages (or, and I cringe to admit this now: scarfing down two slices of pizza on the way to the subway station); dwelling in a studio so cheap it afforded me bragging rights, but so small there was no room for anything but my bed, a bookcase, and a piano (which was also so cheap it afforded me bragging rights... until it wouldn't hold its tuning for longer than a couple of weeks).

But being a starving artist is a form of paying one's dues to their art. Poverty in service of creativity is regarded as noble. An older mentor of mine used to say, with an air of reverence: "When I was your age, I never knew where my next paycheck was coming from." 

So there I was - barely thirty, at said miserable odd job, probably in the middle of a blood sugar crash from all the pizza - and I get a text message.

"I have an idea for you. Quit your job."

And if your friend jumped off a bridge...

I know, I know. How many people in your life would tell you to quit your job? Moreover, how many people could send a text like that and get you to actually listen?

The text, though, is from my good friend Dorie Clark, who is a successful consultant, business author, and entrepreneur. Dorie is the kind of person who's never short of brilliant ideas. I know this because she's had game-changing insights about my music career - the kind that put me directly on the path to Carnegie Hall. And so, I've grown to take her ideas seriously. This one has a good plan behind it. Brand yourself as a virtual assistant; once you have a few clients lined up, give notice. You'll probably make as much money as you're making now, if not more, and you'll have more time and energy for your music.

Here's why that was an easy sell, and one of the hardest things for me to admit for all of the internet to see: I'd come home with under $15,000 the year before.

I set things up and then set a date: May 16, 2016, my 30 1/2 birthday, was the day I'd begin with my new clients.

From VA to Consultant: finding my place in the market

My virtual assistant work grew slowly but steadily for the first six months or so; after a while, private clients started coming to me for one of a few services, and I filled out my income and my time by working with a few online firms. As my clients' faith in me grew, and more clients began to come to me via referral, my place in the market began to unfold. Clients started coming to me for one of three things, generally: social media, podcasts, and TEDx. As I solidified my offerings (and began to have a track record of client satisfaction and success), I transitioned from calling myself a virtual assistant to a consultant.

As I write this, my business is just shy of three years old, and it's grown steadily. Between the beginning and the end of 2018, my business' monthly income nearly tripled. I attribute that kind of growth to a combination of unbelievable luck and sheer force of will. It's taken a lot of hard work, but it's also been a blast. I found a fundamental truth about what makes me feel happy and fulfilled in starting and growing my business, but it was also not always easy. Here are some lessons that I learned the hard way.

  1. Get help. This was one of the hardest lessons for me. In my music career, it'd been a point of pride to do everything myself, and when I started my business, I approached it the same way. It's still a default for me. Facing the kind of growth that 2018 brought me, though, I knew I needed support to help my entrepreneurial business run. Healthy growth of a business requires infrastructure, so my business forced me to get familiar with what I'm not good at so that I can find someone who is good at that particular thing. At this stage, I freely admit that I can't live without someone to keep my professional calendar and inbox in order, and someone to help me identify and build relationships with good podcast hosts. The alternative is not pretty. But there's another, unexpected benefit to getting help - hiring the right people means having more eyes and ears on your business. Because I have the right people on my team, I can expand my offerings outside of things that I, exclusively, can do, and I can get another perspective (usually one that I didn't think of) on the challenges we face.

  2. Guard your time. Pro tip: being an entrepreneur means setting your own hours. But if you're busy, and successful, and growing, you still have a lot of work that absolutely needs to get done every day. When I was first starting, I said yes to lots of long lunches and midday phone calls and coworking-sessions-that-were-really-hangout-sessions with lots of my freelancing friends, but I'd find myself working late into the evening to get everything done. I still say yes to coworking sessions with a few entrepreneur friends (who are judicious about getting work done, too) and to having someone join me for lunch, but I'm far more careful with my time these days. Says freelance writer Dianne Gebauer, who is also one of my favorite people to cowork with: "As a freelance writer who works remotely, it’s so easy to get stuck in a pattern of piling on work and deadlines for hours at home, while forgetting to prioritize self-care. Finding the right people with which to co-work has helped me tremendously in that respect.”

  3. Learn to say no. Practice it in the mirror. Role play with your friends. I am terrible at saying no, but I've had to exercise this business muscle many times throughout my career. You'll have to say no to many things, and chances are that the more successful you become, the more often you'll have to do so: scope creep (Google it: it sounds funny but it's a real thing), unreasonable requests (I've got a personal running list of my all time favorites), networking coffees that turn into requests for free advice (lol), and much more. (NB: I still agonize every time I have to say no. Every. Single. Time.)

  4. A great client is priceless. This will speak for itself. A great client may come in the form of someone whose work you wholeheartedly love and believe in; of someone who challenges you to grow; of someone who is a joy to work with; or all of the above. Great clients are the foundation of what brings me profound happiness in my business - doing work I love for awesome people. Go above and beyond (healthily - be sure to avoid scope creep) for your great clients - these great working relationships are the ones that will help grow your business. I'm grateful every day for my great clients.

  5. Repeat after me: Mistakes happen. And I break into a cold sweat every time I discover that I've made one. It happens: bring it to the client's attention (bonus points for already having fixed it), and have a plan for moving forward. Often, if you've built a good working relationship with a foundation of good work and trust, a good plan is good enough. And then: forgive yourself. Take a walk, go to the gym, write in your journal... do whatever it takes to move on.

  6. His name is Murphy, and his word is the law. Murphy's law is real. Are you sick? Chances are, your VA will be too, according to the statistics of pure dumb luck. Also, that will be the week that your clients will have referrals for you, and these new potential leads will be fantastic people that you'll want to work with and they'll be eager to have a phone conversation with you and you'll have to decide between talking to them with a frog in your throat or waiting till you're better. (Wait. I promise you, from experience, they'll understand.) Have to get up early tomorrow for a big meeting? You'll probably be up the night before, and because your mind is racing, you'll have lightning strike for what you believe is the best blog post idea ever. Roll with it - it'll all be a part of your entrepreneurial story.

"But do you still play?"

I get asked this question from musicians and business folks alike. My entrepreneurial journey has led me to a very different-looking life - one that looks very different from when I was a full-time musician. Instead of spending much of my days practicing, or composing, or looking for my next big project, I'm now focused on my business. But the answer to this question is YES, I still play. In fact, because I have my business, I'm lucky enough to be able to only have room in my life to take the gigs I'm excited about. There's a certain NYC avant-garde theatre company that I make sure to always say yes to when they call.

Getting to only take the gigs I'm excited about is a luxury that I wasn't afforded when I was a full-time musician, but it's also a necessity. Building and maintaining my growing six-figure business takes the majority of my time and energy every day. And it also takes every ounce of my creativity, which I wouldn't have without music.

What have been the biggest lessons you learned on your entrepreneurial journey?

Marie Incontrera