Five4Friday: The Importance of Learning to Sell

Why Learning to Sell is the Ultimate Life Skill and How It Can Transform Your Career, Finances, and Relationships.

The Stereotype That Gives Sales a Bad Name

For many people, few things make their skin crawl more than the thought of a used car salesman. You know the type: desperate, wheeling and dealing, saying anything to close the sale. That stereotype has given sales a bad reputation. But the truth is, sales make the world go round.

Sales Are the Engine of the Economy

Sales are the engine of the economy. They drive revenue, keep businesses running, and fuel growth. There’s a saying I love:

"It doesn’t matter how great your product is if you can’t sell it."

It’s irrelevant. No one will ever know about it.

Learning to sell isn’t just a skill for salespeople. It’s a skill for life. But here’s a question: Is your inability to sell holding you back? Is it preventing you from getting an idea off the ground or earning the promotion you deserve?

My Journey from 'Icky' to Insightful

I didn’t always appreciate this. Like many, I once thought sales were “icky.” In college, I tried selling Cutco knives. You know, those knives I'm sure you had a fried or two that sold at one point. I called up all my parents' friends, pitched them the knives, and sold a few sets. I even had to buy my own demo set, which I still have and use 25 years later. Despite the knives being great and still treasuring them to this day, I still felt uncomfortable trying to sell them.

But I knew I needed to change my mindset. Before going full-time at nuCloud, my own startup SaaS company selling to higher education institutions that we later sold to private equity, I spent my last six months at HubSpot in a sales role, selling to nonprofits and higher education. I learned more about human psychology in those six months than I had in the rest of my career. I discovered that, for me, selling wasn’t about pushing a product. It was about becoming a trusted advisor. Not all salespeople follow this approach, but it’s the one that worked best for me. I gave people honest insights and recommendations, and they appreciated it.

I learned that you can sell with integrity. There are many sales styles, and not all are slimy. Some are rooted in honesty, expertise, and a genuine desire to help. But one thing is certain: you must learn to sell. If you don’t, someone else who can sell will always have an advantage over you.

Sales Skills Are Life Skills

Sales are everywhere. You sell yourself in job interviews. You sell your ideas to your team. You even sell your kids on eating vegetables or going to bed on time. The world runs on sales, and those who understand this are better equipped to succeed.

That’s why I’m teaching my kids about sales early, using yard sales and treasure hunting as a fun training ground. I let them negotiate. They learn to decide what something is worth, ask for a price, and negotiate if it’s too high. Most importantly, they learn that it’s okay to walk away if they don’t get a price they’re comfortable with. It’s a low stakes game where they get a budget and learn how to shop within it. But it’s also a life skill.

The Tip: Embrace Sales as a Skill

So this week’s tip is simple: Learn to sell. Don’t shy away from it. Embrace it. The world is full of opportunities for those who can confidently and honestly sell.

Learning to sell can unlock countless doors. It can lead to career advancements, better negotiations, and stronger interpersonal skills. It can help you have uncomfortable but necessary conversations about money, give you the confidence to walk away from bad deals, and teach you resilience because most salespeople fail more than they succeed.

Sales also teach you how to communicate with strangers, listen actively, and understand what others truly need. At its core, selling is about problem-solving. It means helping others find solutions, whether that’s through your product, your service, or your expertise and getting compensated for it.

If you can sell, you can navigate almost any situation life throws at you. So start practicing. Challenge yourself to negotiate, even on small things. Put yourself out there, get used to hearing "no," and learn to keep going.

Have a great weekend, and I’ll see you next week for another Five4Friday!