How To Make Money: Get Over Your Hate of Selling

Photo by Gus Moretta

Photo by Gus Moretta

When you’re at a bar at 1am; you’re not drunk, but not not sober, surrounded by a bunch of friends, the last thing you want to do is load several heavy, oddly shaped items into a car only to have to unload them shortly after. This is the worst part about playing in a local band; you have to do everything yourself… but it’s just part of it. It comes with the territory. 

To my freelancer friends and small business buddies who hate selling or pitching or talking about the money part of things. I get it, it sucks, but too bad. It’s the trade off for being able to spend your working life building something you believe in. It’s the cost of mostly being in charge of your life. Talking about money doesn’t have to suck. You can stop hating it, but you have to do some work to change your own perspective on it.

Here are some ways I think about selling. I hope some of it will light up your brain and help you power past some of your limiting beliefs around selling and talking to customers about money.


Don’t put pressure on the sale; shift your focus 

Selling something to someone is like throwing a paper airplane. It’s easy to get focused on a single isolated event, like actually throwing the plane. But there are other factors and conditions that impact whether the plane will fly, float, coast or crash.

From the kind of paper you choose, the type of plane you choose to make, the amount of experience you have making planes (which can impact your confidence level), the way you stand, how you hold the plane and when you release it from your hand are all factors that impact the simple result of will the plane fly?


Selling isn’t one isolated event

Every interaction with a potential customer is part of the sales process. Selling isn’t just an isolated event, it’s connected to everything you in your business. If you do all the foundational work to really, truly, understand the people you’re serving and helping, selling can be easy because the work you’ve done getting to know your target market informs how you should be selling. This foundational work then impacts other factors like your company's social media strategy, the content you’re creating, how you’re putting it out there and the types of press you’re getting. All of these things impact and inform your potential customers and your target market. It’s all part of the selling process.


Make sure the thing you’re selling is awesome

I used to suck at selling. My first real job right out of college was a total shit show. I was telemarketer that had to dress up for work. I had no clue the it would be mostly telemarketing, but the job was, of course, sold to me by the sales manager and at the time I was too stupid to ask critical questions.

After a couple of weeks in training, I got on the phones. I was horrified when I realized the financial products we were trying to sell to people were a level below dog shit. I cared about our target market, but mostly because I knew the practices were predatory. Caring about them meant I didn’t want to sell them our products because it wasn’t in their best interest. I spent an entire working week not making a single sale and quit.

If you don’t believe in what you’re selling because you don’t think it’ll really help people or because it’s a giant pile of crap, you’ll have a difficult time trying to sell it. 



Be a real person

Some years later, I eventually got into another job where I would eventually work my way to selling again. And I still sucked. This time the service we were selling was top notch, the team I worked with was supportive, my boss was brilliant, and we were helping people in a real, tangible way. But still, I sucked. I only realized why in hindsight. First, building real skills takes time. Second, I rarely signed clients because I was acting like a bizzaro version of myself. I was a projection of what I thought people wanted me to be - I took myself too seriously, I was professional to a fault, and I wore a stupid blazer! As soon as I stopped being robot Paco and started being regular Paco, selling got less weird because I was making people feel less weird.



Tell the story about how you help people change or reinforce their ideas about themselves. 

Whatever you’re selling, you generally have three options for framing it:

  • You’re selling the idea of change,

  • reinforcing someone’s idea’s about themselves or

  • you’re just selling a the thing you’re selling, which means you end up selling a commodity. When you just sell a commodity, no one knows why you’re thing is special, so you aren’t and then it becomes about price.

Let’s just look at blenders for an example. If you wanted to sell blenders, you have options for how to tell a story to you target market. You can be a brand that will sells blenders by selling people a better version of themselves. Your brand will say, “If you buy this blender, you’ll change into a healthy person or you’ll be the type of person who cooks more". Your messaging will be all about how your customer can change into a more awesome version of themself when they buy your blender.

Then there are the options that reinforces your target market's identity. Is your market the type of people who always get the best option, the top of the line? Are they early adopters who want a blender that is connected to their phone for some terrible reason? If that’s your audience, your brand will tell a story that reinforces that idea of who they are - a digital native who wants a top-of-the-line blender that can blend 7 lbs of aluminum cans in 12 seconds! The messaging will be all about how they're already this type of person and these type of people buy your blender.

And lastly, if you don’t choose a story to tell to a group of people you’re trying to sell to, you don’t have a story, you just have a blender. You might try to sell blenders to anyone. When there isn’t anything that sets you apart, the one thing that can is price. This is usually by default. And this is tough. Competing on price means finding cheaper labor and cheaper inputs in order to stay competitive. So instead of putting energy into making things better, you have to keep finding ways to cut back on costs. This is a race to the bottom in price and quality. 

When you’re focused on the people you serve, you know what stories to tell.  



If you don’t want to work with someone, you don’t have to

That’s the beauty of working for yourself and a huge benefit of really caring about all this foundational marketing stuff - you can pick who you want to work with and you can avoid being desperate. If you don’t get good at marketing and selling, you’ll be stuck taking what you can get instead of being able to pick from all your options. When you don’t have a real choice, you may as well be working for someone else.



Avoid being desperate (or pretentious) by not making it about you

Desperate is the kiss of death in business. When people sense desperation from you, no one will want to have anything to do with you. The best way to avoid coming off as desperate, even if you are, is to not make it about you. Desperate people are profoundly concerned about their own needs, wants and desires.

Go into the back of your filing cabinet of your memories and think about high school. It was a time when everyone was desperate to be liked. Wasn’t there always someone who acted thirsty AF? Maybe they were obnoxious and loud and tried to get a bunch of attention because deep down they were desperate to be liked? And by contrast, there were always the shy, quiet ones, who were equally as desperate, but because they sat quietly and listened and didn’t constantly make things about them, people didn’t smell their desperation as much.

So if you’re worried about coming off as desperate, just remember to listen and care. Figure out how to care more about them and less about you. People will always remember how you make them feel because vibes are real.

Spectrum of Desperation + Pretention.png

Seriously, it’s just not about you

Talking too much about yourself might not make you look desperate, it might just make you look like an ass. I can’t tell you the number of times I’ve gone to a party, met someone new and then proceeded to let them talk about themselves the whole time. I ask them questions about their work and their personal history and just let them wax poetic about the thing they know most about: themselves. And 90% of the time, they leave the interaction knowing next to nothing about me, but will unabashedly tell me how wonderful it was talking and that they’d love to hang out. And it’s because they’re high on their impromptu cabaret performance and can’t wait to do it again. I’ll never hang out with that person because they will capitalize on the opportunity to have a monologue with a participant who may be too exhausted to put up a fight. With business and selling, it’s definitely not about you. Open up a cold, refreshing can of self awareness and make sure your approach isn’t all about you. 


Ultimately, they have a problem and you have a potential solution 

Don’t forget to talk about this. Sometimes I’ve even just asked potential clients, “So, what are some of the problems you’re experiencing that I can help you with?” It’s clear, it’s about them, and you’re framing it in the context of helping them. If you’re selling online and not in person, you can still create the problem-solution conversation. Just look at the awesome and terrible example of informercials. They always lead in with some albeit weird problem and their product is always the solution. Never forget that somehow lots of Snuggies got sold; and just look at all the problems they solved for our great country.



Patience, Grasshopper 

Overnight success can happen in as little as 5-15 years. Be calm, stay relaxed, be patient and consistent. If you put out frustrated and impatient vibes, that’s what’s going to come back to you. In many, many ways, always remember: you get what you give.