My dad sold million-dollar systems out of a suitcase. I sell books and ideas from a laptop. The technology changed. The part that actually matters didn’t.
By Curtiss Wayne Andrews
There is a word that makes a surprising number of creative people uncomfortable.
Sales.
Tell someone you’re starting a side hustle and they’re excited.
Tell them you’re creating a book, designing T-shirts, opening an Etsy shop, freelancing, consulting or launching an online business and they’ll cheer you on.
Tell them they need to learn how to sell?
Suddenly everybody looks like you just invited them to spend Saturday afternoon at a timeshare presentation.
I understand it.
For years, I thought selling meant convincing somebody to buy something they didn’t particularly want.
I’ve come to believe almost the opposite.
Good selling is helping the right person understand why something you created might solve a problem they already have.
And I learned that lesson from someone who was selling long before Instagram, Etsy, Amazon KDP, TikTok or the phrase “side hustle” entered our vocabulary.
My dad.
When Selling Required a Suitcase
Back in the 1980s, my father worked as a national sales representative for Syva, a company known for diagnostic testing technology.
His version of working remotely didn’t involve Zoom.
It involved airports.
Lots of them.
He traveled around the country selling sophisticated drug-testing systems to organizations that needed reliable testing capabilities.
That meant courts.
Correctional facilities.
Major corporations.
And other customers where getting the answer right actually mattered.
There were no email funnels quietly working while he slept.
No Facebook retargeting ads.
No Shopify dashboard telling him somebody in Des Moines had abandoned a shopping cart.
If he wanted to make a sale in Texas, there was a decent chance he had to go to Texas.
Suitcase.
Rental car.
Hotel.
Presentation.
Meeting.
Dinner.
Another meeting.
Airport.
Repeat.
My brother and I became quite familiar with takeout and TV dinners.
But here’s the thing I didn’t appreciate when I was younger:
My father wasn’t really selling equipment.
He was selling confidence.
The customer had a problem. His job was to understand that problem well enough to explain why his company’s solution made sense.
That’s sales.
And nearly 40 years later, that’s still sales.
Your Side Hustle Has a Sales Department
Here’s the bad news for anyone hoping to start a side hustle without learning to sell:
You already have a sales department.
It’s you.
If you publish books, your Amazon description is a salesperson.
Your cover is a salesperson.
Your title is a salesperson.
If you sell print-on-demand products, your thumbnail is a salesperson.
If you’re a freelancer, your portfolio is selling.
If you’re a consultant, your first conversation with a potential client is selling.
If you make sourdough journals, caregiver logs, coloring books, training planners or some wonderfully strange book about vintage Christmas decorations, you are selling every time you explain why someone should care that the thing exists.
I’ve learned this firsthand.
Paper Sack Publishing encompasses books in wildly different niches.
That means I can’t simply make something and announce:
“LOOK! I MADE A BOOK!”
Nobody cares.
Nor should they.
The customer cares about what the book does for them.
That’s a very different question.
Stop Selling the Thing
This may be the biggest lesson I’ve learned.
Don’t begin by selling the thing.
Sell the outcome.
Suppose you’ve created a sourdough baking journal.
You could say:
“This is a 120-page sourdough logbook with recipe pages and fermentation tracking.”
Perfectly accurate.
Also perfectly capable of putting someone to sleep.
Instead, understand the frustration.
A home baker finally creates an extraordinary loaf.
Perfect crust.
Great oven spring.
Beautiful crumb.
Then tries to recreate it three weeks later and realizes:
“I have absolutely no idea what I did.”
Now you have a problem worth solving.
The journal isn’t really selling blank pages.
It’s selling the ability to repeat your best results.
That’s sales.
The Same Lesson Applies to Almost Everything
A caregiver log isn’t paper.
It’s a way for an exhausted family to communicate important information between shifts.
A training journal isn’t a collection of grids.
It’s a way for an athlete to see progress that can otherwise disappear into hundreds of individual workouts.
A family recipe book isn’t blank recipe pages.
It’s insurance against Grandma’s stuffing disappearing when nobody remembers exactly how she made it.
A book about vintage collectibles isn’t merely information.
It’s helping someone recognize the object they just pulled out of an estate-sale garage.
Once you understand the problem, selling becomes considerably less uncomfortable.
You’re not trying to manipulate someone.
You’re explaining the connection between their need and your solution.
My Dad Had to Get on an Airplane. You Have It Much Easier.
This is where today’s side hustler has an almost ridiculous advantage.
My father’s potential customer might be 1,500 miles away.
Today, yours might be 1,500 miles away too.
The difference is that you can reach yours before breakfast.
You can publish something on Pinterest.
Post a short video.
Send an email.
Write a blog article.
Test a new Amazon cover.
Change a product description.
Run a small advertisement.
Rewrite a headline.
Publish another version.
The cost of testing an idea has collapsed.
That’s extraordinary.
But it creates a trap.
Because when technology makes distribution easy, people start believing distribution is selling.
It isn’t.
Getting 10,000 people to see something nobody wants isn’t a business strategy.
It’s just a larger audience ignoring you.
Listen Before You Pitch
My father spent his career sitting across tables from customers.
That forced him to listen.
Online entrepreneurs can easily avoid that step.
We can sit alone with our laptops and convince ourselves we’ve created exactly what customers want.
Then launch it.
Crickets.
Then blame the algorithm.
Sometimes the algorithm isn’t the problem.
Sometimes nobody wanted the thing.
This is why reviews, search terms, Reddit discussions, Facebook groups, customer questions and even negative comments can be extraordinarily useful.
People will tell you what bothers them.
They’ll tell you what existing products get wrong.
They’ll tell you what they wish existed.
Your job isn’t always to invent demand.
Often, it’s simply to notice it.
Learn to Describe What You Do in One Sentence
Here’s a useful exercise.
Explain your side hustle without using industry jargon.
If you can’t explain why someone should care in one or two sentences, your customer probably can’t either.
Not:
“I provide innovative lifestyle solutions designed to empower entrepreneurial creators.”
I don’t know what that means.
Try:
“I create practical journals that help people track complicated things they don’t want to forget.”
Now I understand.
Clarity sells.
Confusion doesn’t.
Rejection Isn’t Nearly as Expensive Anymore
This may be the biggest advantage today’s entrepreneur has over my father’s generation.
Imagine flying across the country for a presentation.
Hotel.
Rental car.
Meals.
Hours preparing.
You walk into the meeting.
They say no.
That’s an expensive no.
Today?
You can test a product listing and nobody clicks.
Change the headline.
Try again.
Run an ad and nobody buys.
Stop it.
Change the offer.
Try again.
Publish a book and the cover isn’t working.
Replace it.
Your failure can cost $20 instead of $2,000.
That’s an incredible gift.
Yet people still treat a failed experiment like a verdict on their ability.
It isn’t.
It’s information.
Don’t Confuse Persistence With Repeating the Same Mistake
This is another place where sales teaches an important lesson.
Persistence matters.
But if something repeatedly doesn’t work, doing exactly the same thing harder isn’t necessarily perseverance.
Sometimes you need a different product.
Different audience.
Different price.
Different headline.
Different image.
Different offer.
Different channel.
The modern side hustler has access to something my father’s generation would have killed for:
almost immediate feedback.
Use it.
Sales Isn’t a Dirty Word
I’ve spent a lot of my career around creative people.
Writers.
Designers.
Marketers.
Artists.
People with ideas.
And I’ve watched talented people sabotage themselves because they believe the work should somehow sell itself.
Occasionally it does.
Usually it doesn’t.
You can write a terrific book nobody discovers.
Create a brilliant design nobody clicks.
Offer a useful service nobody understands.
The quality of the product matters enormously.
But so does your ability to communicate its value.
That’s why learning sales doesn’t make a creative person less creative.
It gives the creativity a chance to survive.
From the Suitcase to the Sofa
Sometimes I think about how strange my working life would look to my father during his traveling-sales years.
I can create a product at home.
Publish it without owning a printing press.
Sell it to someone I’ve never met.
Market it while sitting on my couch.
See whether people clicked.
Change the message.
Try again tomorrow.
He needed plane tickets, expense accounts, presentation equipment and a suitcase.
I need Wi-Fi.
But beneath all that technology, the fundamental exchange hasn’t changed very much.
Someone has a problem.
You listen.
You understand it.
You explain why what you’re offering might help.
And then they decide.
That’s sales.
Not trickery.
Not pressure.
Not convincing somebody to buy junk.
Understanding people well enough to make something useful — and communicating that usefulness clearly enough that they recognize it.
If you’re building a side hustle, learn that skill.
The platforms will change.
The algorithms will change.
The software will change.
The trendy business models will definitely change.
But somebody will always have to answer the customer’s most important question:
“Why should I buy this?”
Learn to answer that well, and you have a skill considerably more durable than whatever platform happens to be hot this year.
My dad needed a suitcase to do it.
You can probably start from the sofa.
Want to Build Something of Your Own?
Curtiss Wayne Andrews is the author of Side Hustle Revolution: Launch Your First Money-Making Project With Zero Experience, a practical guide to moving from “I should really start something” to actually testing, launching and selling your first side project.
Because the goal isn’t to spend another six months thinking about starting.
It’s to find out whether somebody will pay you for what you can create.