I’ve learned a lot in the twenty years since I first became a small business owner. In that time I've digested a lot of wisdom about what healthy entrepreneurship looks and feels like.
For a long time I carried a lot of self-judgment around my first experience with starting a business and shied away from sharing any of this. Now, having integrated a lot of these lessons, I feel that if my experience can help anyone who’s just getting started, it’s worthwhile to talk about it.
At the time of starting my first business, I was under a lot of pressure. I had just quit my university teaching job on the premise of wanting to start my own thing, when the deeper truth was, it was just time - for many reasons - to move on. While I was sure that was the right decision, I had traded the security of a regular income for that freedom.
To compound the stress, I had also recently purchased a home. I was counting on rental income from the roommate who had first agreed to take one of the three bedrooms, and abruptly abandoned that plan for a more enticing opportunity. I wished her well then, and still do, though I can’t deny the terrifying financial bind it left for me.
You might ask, as I have many times over the years, why purchase a home if you couldn’t afford it alone? Well, it was what I considered a strategic investment. It’s difficult to teach singing and piano lessons in an apartment complex and maintain good relationships with your neighbors. A home with a third bedroom for a studio was just the ticket, in my 26 year old mind. True to form, I leapt and trusted the net would appear.
The final layer of pressure I felt came from within. I desperately wanted to prove I could do this - that I was able to be independent and build a life for myself that would not require me to compromise my own needs, desires, and values. I wanted to go my own way.
In the beginning, everything was going so well. Students were appearing through friends and referrals, coming so easily that I didn’t even have to advertise. I could just focus on creating good experiences and honing my teaching craft. I held recitals and successfully prepared students for auditions. I built a referral network with music teachers in other disciplines and wrote my first contracts covering the terms of referrals and commissions. I felt I was made for this.
Still, under all of that initial success, there were issues I wasn’t dealing with. I worried constantly about making more money and obtaining more students. I grew to loathe teaching certain styles and pieces of music that students wanted to perform and wondered, “Can I really do this every day for the rest of my life?” I pushed that voice down as fast as it came up. Those kinds of thoughts felt dangerous. The briefest idea that perhaps this wasn’t the perfect scenario for me felt like a threat to my survival. This had to work.
A couple years went by, and my business began to slow down. The housing market crash of 2008 and the great recession were not kind to my client base, and consequently they were not kind to me. I put effort into new ways of marketing and finding new referral sources, but nothing really provided the wellspring I needed. I am certain that the desperation in my voice was partly responsible - repelling the very people I needed - but at the time, it couldn’t be helped. At this point, I’d spent two years rehearsing fears I wasn’t resolving, and I had no tools to deal with this crisis. I was self-sabotaging, in a mental health low, and I wasn’t sure I even wanted to keep trying.
It’s cathartic to put all of this down on paper, but I’m not writing a journal entry. This story outlines one possible route a new solopreneur can take when they begin their journey. Let’s just say, I took this painful route so that you don’t have to.
I’ve come to learn over many years of entrepreneurship and working side by side with founders that if you want sustainable success, one of the first things you must do is deeply understand three questions:
- Who am I?
- What do I care about?
- How do I want to demonstrate that in the world?
I teach this in my work with early-stage entrepreneurs, both in group sessions and private advisory sessions. It’s what I start with because it helps to uncover the hidden fears we have and the decisions we’re making that aren’t truly in alignment with us. It’s truly the core identity - the spine - of yourself and your business, and it’s the very thing that will create resilience in your business. Without establishing these governing variables, you are at the mercy of the circumstances in which you find yourself, constantly making surface level tweaks that aren’t addressing the core issues.
If I’d understood those three things to the fullest extent possible at that time in my life, perhaps I would have realized the enormous pressure I was putting on myself by leaving my full time job, buying my first house in a financially disadvantaged position, and starting a business I wasn’t fully sure I was even going to enjoy. Whether I changed a single one of those decisions or not, I would have known. If I’d had the tools in the beginning stages of opening my business, I might have been able to adjust and face my fears when difficult circumstances arose.
For example, when it started to surface that I wasn’t loving everything about this career path, I could have more fully examined it. Perhaps I might have made a change that was more aligned for me, instead of engaging in unconscious self-sabotage. I, and my business, were too fragile to flexibly explore any of this because we were operating without a spine. The only governing variables were “make more money,” and “this has to work or else.”
I call this stage of business planning The Void because it’s like a gestation period. An in-between time, or liminal space. Where what will be is not yet. The fallow, dark, fertile emptiness that allows inspiration to grow, be refined, and come into clarity.
It is in the Void that our vision becomes palpable enough to sustain us through all of the ups and downs of the entrepreneurial journey.
In The Void (in addition to the nuts and bolts of starting their business), a founder takes the time - how much varies from person to person - to mull over their idea deeply. This time in The Void doesn't mean delaying your other business planning and preparation, it means slowing down your internal frenzy so that the actions you take actually help you get to where you want to be.
The contemplation in this stage brings the founder face to face with their deepest assumptions about the leap they’re taking. I guide that inquiry not only as a business strategist, but through the lens of somatic awareness, understanding of the heavy social conditioning we all live with, and self-compassion work. You’ll answer questions like:
- Why this idea?
- Where did this come from?
- How does it align with my sincerely held, non-performative values?
- If no one else had any expectations of me, would I still want to do this? And in this way?
- In my professional life, I learned (explicitly or implicitly) that in order to succeed, I needed to do x, and that’s impacting my vision by:
The Void is never truly finished, because we’re constantly learning and evolving and peeling back the onion of our psyche. But we do reach a point where to stay in this stage any longer without taking action would mean we’re simply procrastinating. Once participants have finished this preparatory phase, they’re equipped with an understanding of:
- What truly drives them in this effort
- What will sincerely get them out of bed every day to work on it
- What kind of boundaries will make it sustainable for them
- What kind of impact they plan on making.
They’re ready to pulse their vision out into the world.
My 26 year old self did not have access to this kind of business planning. She is both grieving that lost opportunity and cheering me on in sharing this personal experience. Now that I’ve integrated these lessons and many more, I no longer hide from the fears that come up on my journey. I’m able to name and face the things that come up internally, and I go back to my foundation. I make my decisions from that unshakeable base, rather than fear, pressure, or any outside influence. I still take risks and trust that the net will be there, but I am able to better navigate and enjoy the trust fall now.
If you are starting up a venture, or find yourself facing fears and self-sabotage in your business now, I invite you to reach out. You don't have to build this foundation alone. I partner with founders and business leaders at different parts of the growth cycle: some just starting, some scaling, some rebuilding after a challenge. I would love the opportunity to help you create the thing you really want to build in this world.