With the advent of more freelancers in our disintermediated economy, I am frequently asked, “How long have you been in business for yourself?” This year’s answer: “I am going on my 20th year,” which usually launches a whole conversation that goes something like this.
Them: Do you enjoy going solo?
Me: Yes.
Them: Do you have any tips?
Me: Many.
Them: Should I do it?
Me: Do you like to sell?
Selling is my starting point as the be-all, end-all of successfully running a solo business because it’s what gives us the opportunity to deliver our goods. I didn’t realize this at the start and would only have described myself as curious, people-centric and hard working. I like to think that I build relationships for the long run. I usually know whether a particular client prefers Starbucks or Dunkin Donuts, a tidbit about their family, a hobby that they love, and if we are particularly close, maybe a personal storm they have weathered.
In my two decades of going solo, I have discovered that curiosity and relationship building are just the qualities needed to sell — along with gentle persistence. Curiosity helps to identify the challenges. Relationships help customers believe that we will do exactly as we say. “Gentle persistence” prods us to treat stop signs as yields, and “no” as “not yet.” It is a finesse move where we are chill on the surface but furiously paddling underneath.
I particularly understood the value of these qualities when I hit a big speed bump in my 18th year of solo consulting. Until that point, I had benefited from a good run with a few valleys that never felt bigger than me. Then I hit a wall. A prominent client who accounted for more than half of my billings decided to retire. While he had given me signs that he was fatiguing from the constant travel and organizational turmoil, I had heard it before. When the announcement came, I had not planned how to fill the big ditch in front of me.
I experienced angst followed by self-talk: “Do the sensible things you tell your clients.” I secured my existing client base and sought to expand my footprint, though most everyone seemed to be in a budget crunch. I reached out to my network of colleagues who knew me but hadn’t hired me. I wrote pieces for various publications that got claps but alas no purchase orders.
I sought relief by hitting a tennis ball extra hard, walking my dogs, doing more self talk, and eventually reaching out to a colleague who had become an executive recruiter. I wanted to test my market value.
The colleague-turned-recruiter (John) listened to me and then asked a series of questions, many of which I had asked myself. “How much do you expect to earn?” “What would it feel like to not be your own boss?” Then came the question that stumped me: “How should I, as recruiter, address the question that I will invariably be asked: After 18 years of working for herself, why does Jill want to be inside an organization?”
I knew the answer could not be, “This is an urge born of desperation.”
The closing moment of my call with John was my eye-opener. “Jill,” he said, “for as long as I’ve known you, you have been able to sell your ideas … sell yourself. Your years of successfully running a business speak to this. You are born to sell.”
He counseled me to take a break, recharge my batteries, and then get back on the horse. “You will do financially better there than anything I can offer you, and you will be happier.”
After a moment of silence, John added, “I was born to sell too, and I also have run into those times when you are tired, and you just don’t know whether you have it in you anymore. But you do.”
His wise counsel at a vulnerable moment was helpful. I have made a note to pay this forward. I got back on the horse. I drew up a plan, which included reconnecting with colleagues, writing and expanding my offering.
In the process, I learned that “gentle persistence” was not only helpful with clients but also for me. Over time, I created a new reality. I began writing speeches for clients. I gave some talks. I focused on smaller companies both to do something different and because of the kinship I feel with small businesses. Growing up, I ran the register at my parents’ grocery store. While consulting is far different than cashiering, every time I’ve had the opportunity to go small, I’ve enjoyed it.
I’ve also changed my metrics. Billings and backlog are still important, but they don’t rule the way they once did. My second act makes room for supporting my hobbies, of which writing is one.
My question to others, “Do you like to sell?” comes from my experience about sustaining a business for the long run. Selling should be viewed in a positive light and embraced. We are not, to adopt an old expression, “used car salesmen,” nor are we “pulling the wool over peoples’ eyes.”
We are exhibiting faith in ourselves. We are using our curiosity and relationships to address needs. We are demonstrating a subtle mix of patience and persistence to enable a long ride.
