What to do when you’re afraid of “selling out”

“Is this something you’d be interested in paying for?”

It was an innocuous question that I’d sent to a friend via Facebook Messenger. No one could have suspected this was anything other than a serious and confident query. Only I knew the truth: Behind it all was this big knot of dread and anxiety so bad that I briefly considered the ways I could undo the message. Maybe if I drove to their house and got there before they did …

Less than a minute — the longest minute ever — must’ve passed before the ellipses that indicated someone’s typing a response appeared. I leaned in and waited with trepidation while my stomach did dolphin flips and a tiny voice somewhere in my head screamed, “AHHHHHHHHHH!” Then, his answer came:

“Okay, I’m in. How do I pay you?”

An actual human being was willing to pay me actual money for an idea!

“Oh, ummm, PayPal…?” I responded.

And that flaccid response was how I made my first sale for my first-ever product — a beta-version online workshop on landing your articles in major media outlets (and for niche sites like GrowthLab too). This whole exchange might seem pedestrian, but before that moment, I had not heard a sweeter combination of words. It’s like that moment when you take that first sip of coffee in the morning. The very same when you pull your head from underwater for that first gulp of air. No one prepares you for that moment.

Everybody tells you that the entrepreneur’s journey is rife with setbacks, interspersed with moments of clarity and confidence-crushing doubt. This could be filed under the “moments of clarity” section.

I thought I’d rather drop a 50-pound dumbbell on myself before I’d sell to someone else, let alone a friend.

It became a thing I told myself anytime I thought about starting a business: I would never sell. But somehow my reluctant thoughts have now pivoted to sell, sell, sell!

When I trace back my year to investigate precisely how and when my perspectives about selling switched, I realize that it was not just one Neo-like “whoa” moment, but actually a series of stand-alone triggers. Trigger after trigger, my old belief systems around sales slowly eroded away until one day the whole thing crumpled and culminated to that earlier moment of asking a friend on Facebook, “Would you pay for this?

If you find yourself held in place by your fear of selling, let me share with you the three major triggers that forever changed the way I looked at selling. The hope is that you too can tackle this fear straight-on and move forward with the business you’ve always talked about and dreamed of.

Here we go.

The first trigger: I’ve actually always been a salesperson

One summer evening in 2017, while visiting Toronto, I attended a dinner with a motley group of CEOs from small enterprises and serial entrepreneurs. Each person was a titan in their own right. I was a writer and freelance journalist.

Sitting to my immediate right was a dapper-looking gentleman who I had guessed was in his late 30s. As is standard protocol in these sorts of social situations, I asked him, “What do you do?” He smiled and told me about his business (a subscription-based company that sends different charcuterie meats every month, if you’re wondering). After some time, the conversation turned to my own work.

Part of what I do as a freelance journalist and writer, I explained, is identify hot and interesting stories and ideas, and pitch them to editors at a variety of publications. Intrigued, he asked me, “How often do editors accept your ideas?”

Without thinking too much on it, I answered, “Maybe three out of five pitches on average.”

The next thing he said was the exact moment of the first trigger.

“You must be really good at selling,” he said.

Good at selling.

The realization felt like the click of a treasure box that springs open with the right key.

You mean to tell me that all this time my “pitching” was actually “selling”? Mind blown. It actually made sense. I walked away that evening with my beliefs shaken, but in an undeniably energizing way.

I believe that most of us have a narrow definition of selling. But as I’ve realized, selling isn’t just getting people to open their wallets. Selling can mean convincing others to part with some sort of resource, whether it’s money, knowledge, time, and so on. Daniel Pink’s “To Sell Is Human”calls this “moving” others and non-sales selling.

Each of us sells every single day: parents cajole their teens to put down their phones and talk once in awhile. Friends urge friends to try their favorite dish at their favorite restaurant. I persuade editors that my idea makes for an interesting story. And so on. In this light, how can ALL selling be slimy and sleazy? Is selling your mom on the idea of rest when she’s sick unethical? Is selling your abilities and skills to a potential client gross?

Selling is what we naturally already do, for good and for bad. It’s a way of life.

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The second trigger: I’m trying to help you, really

Before the convenience of Google, information on used cars was not readily available, which gave used car salesmen the upper hand. They knew things about the car they were selling that you did not. Specifically, whether the car was good or a “lemon.” This asymmetry of information tipped the scales in their favor, and they built a reputation of lying, roughhousing, and cheating their way to a sale.

These days, unless you failed to do your homework, it’s hard for you to be caught off guard by an imbalance of information. We now have the opposite problem: There’s too much information, which can cause confusion and inaction. Our roles are less focused on the sales themselves and more on being the bearers of truth and clarity.

I don’t purport to know everything, but I know certain answers that people seek. And I am confident that I can help prevent them from making frivolous mistakes or wasting their time. If a friend or family member asked whether I could help them, I would give my sincere opinion as any trusted advisor would. If yes, I move them to buy. If no, I tell them flat out. This is the difference between a genuine connection and sale and a skeevy used car salesman.

With this in mind, a sale is not just another sale.

A sale is understanding the person’s dilemma and confusion. A sale is bringing light to the customer’s plight. A sale is listening and nodding along, letting the person know that you clearly understand. It’s empathizing with their pain, however big or small it seems. And I understand now that the sale comes when the person gains a certain level of clarity and trust, and is ready to receive my help. If they’re not, I don’t take their money. I’ve actually turned away people who I didn’t think would benefit from my services and product at that moment.

Knowing that I am turning down sales makes selling all the more empowering for me.

The third trigger: I’ve gained the most important thing of all, trust

In one of my favorite Zero to Launch videos, GrowthLab CEO Ramit Sethi explained that by the time someone gives you their hard-earned money, they have placed a tremendous amount of trust in you. I’d never thought of giving money as an admission of deep trust before, but knowing what I know now, I believe there’s something to it.

We’ve all spent money on things that we’ve regretted before. I’ve spent untold hundreds of dollars on video games that disappointed me. I’ve sunk tons of money on skincare products that my skin negatively reacted to or didn’t accept. But each time I open my wallet, I do so with the belief that there’s something valuable to be gained, and maybe that this time the outcome would benefit me more than the last.  

So to think that someone could trust me enough and fork over their money, despite this baggage, makes me feel good and gives me a sense of responsibility. It makes me feel like I could not let that person down.

What I did as a first-time seller

These three triggers together powered the switch that helped flip my perceptions of selling completely on its head. But they alone weren’t enough. Having not purposefully sold a single thing ever before, I couldn’t be completely convinced I could do it. Money can be a sensitive topic, after all, and the thought of that icy “no” was still a scourge in my mind. Clearly, I had to ease into it.

But how? Where would I even start? What if someone gets annoyed with me?

While these questions churned in my head, I had an idea for an online workshop to help bloggers, writers, and solopreneurs amplify their reach by showing them how to break into more mainstream publications. After all, I had created a framework for it based on years of experience in digital publishing. I decided to test if it would fly.

Let me tell you: even this was scary. What if everyone hated my idea? What if it’s actually a stupid idea?

I reassured myself by saying I wasn’t forcing a sale, I was asking people. If I could just pose it as a series of questions to gauge people’s interests, could that work? If I had treated them as my collaborators working toward a mutually beneficial goal or need, maybe then they wouldn’t think I was just trying to take their money.

It was like trying to convince my friend to try the new ramen place down the street. It was floating an idea and starting a conversation to see where their head was at.

I began by making a list of Facebook friends whom I thought would be most interested and hitting them up. It was casual. I’d say something like:

“Hey, wanted to run an idea by you that I thought you might be interested in.”

Then I’d wait for them to say, “Shoot.”

From this point, I’d personalized every message and said something to the effect of:

“I know you write articles here and there and you’ve probably seen my articles on Lifehacker, New York Times, GQ, Los Angeles Times,and other places. So what do you think about learning my systems for getting published in major publications and other places you want? I’ve been thinking about launching a workshop for this very thing.”

Pause and wait for an answer.

Some said, “Yes, I’m interested!” or “I’m interested, but it’s not something I’m looking for right now. I know others would KILL for this though.”

Based on those answers, I knew I had something.

As I saw my Facebook Messenger light up with messages like, “Yes, tell me more” and “I’m listening,” I swelled with excitement and mustered up enough confidence to pull the trigger with:

“Is this something you’d be interested in paying for?” and other variations of this.

And the rest, as people say, is history.

Kind of a crazy 360: I went from being absolutely terrified of asking for the sale a year earlier to spending two weeks juggling 40 or so ongoing Facebook conversations, asking people to pay me to join my beta. In the end I got 17 people, totaling $5,000.

Nowadays, I am excited to keep making improvements to my next iteration — an 8-week course — and iterations after that, do the whole sales-shebang, and continue to build out and refine my coaching services. I never thought I’d be doing this, but it’s a great feeling.

Those two weeks were an incredible and exhilarating learning experience. Seeing notifications like “You’ve got money!” pop up in my inbox was a sublime feeling that, at the risk of sounding shallow, validated my professional existence.

It hasn’t been that long since my first “real” sale, but something awakened in me that day.

What awakened was the affirmation that selling is not only a way of life, but also in the words of the author Daniel Pink: It’s human.

What about you, my fellow entrepreneur? Have a story to share about overcoming your fear of selling? If not, what’s holding you back? I’d love to hear from you in the comments below!

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Written by

Host of Netflix's "How to Get Rich", NYT Bestselling Author & host of the hit I Will Teach You To Be Rich Podcast. For over 20 years, Ramit has been sharing proven strategies to help people like you take control of their money and live a Rich Life.