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Why selling feels so hard, and how to make it easier

Selling isn't easy. But it's not impossible.
October 22, 2026 by
Jazmin Arredondo

Let me guess. You’re really good at what you do. Your clients love your work. But when it’s time to sell it, something changes. You feel awkward. You don’t want to sound pushy. So you wait for referrals and hope the next client shows up.

I get it. And I want to tell you something I learned after more than 20 years in sales: selling isn’t easy. But it’s not impossible.

Why selling feels so hard

1. Nobody taught you how.

You learned your craft. You learned how to cook, build, design, fix, teach or advise. But nobody sat you down and taught you how to sell it. So you’re improvising, and improvising feels uncomfortable.

2. You think selling means convincing.

Most people imagine a salesperson as someone who talks too much and pushes too hard. You don’t want to be that person, so you avoid selling altogether. But good selling isn’t convincing. It’s listening, understanding what someone needs, and showing them how you can help.

3. You’re selling without a system.

When there’s no process, every sale feels like starting from zero. You forget to follow up. You don’t know where your leads came from. You lose clients you never knew you had.

4. You take every “no” personally.

When you sell your own work, a “no” feels like rejection of you. It isn’t. Most of the time, it means “not now”, “not ready” or “I need more information”.

What actually helps

Treat selling like a system, not a talent.

At my family’s business in Peru, my brother and I didn’t become better salespeople overnight. We built a system: a clear process, simple numbers to track and a lot of follow-up. That’s what made the difference. Selling isn’t about talent. It’s process, numbers and people.

Know exactly who you help.

“Anyone who needs it” is not a client. The clearer you are about who you serve and what problem you solve, the easier it is to find them and talk to them.

Follow up, kindly and consistently.

Most sales don’t happen at the first conversation. They happen after the second, third or fifth follow-up. One message, one call, one “just checking in” can be the difference between a lost lead and a new client.

Write things down.

You don’t need a fancy tool to start. A simple list with names, dates and next steps will already put you ahead. When you’re ready, a CRM makes this easier, and AI can help you save time with messages and follow-ups.

Lead with help, not with a pitch.

Share something useful. Answer a question. Explain how something works. When people learn from you, they start to trust you, and trust is what sells.

One last thing

When I moved to Canada in 2019, I didn’t speak English. I couldn’t sell the way I used to, so I started over. Kitchen helper, cleaning houses, cashier. Today I’m selling again, in English, and the same principles still work: understand people, build a system and keep showing up.

If selling feels hard right now, that doesn’t mean you’re bad at it. It just means you haven’t built your system yet.

Want to talk about your business? Let’s connect. I’d love to hear what you’re building.

Let's connect

This article is for educational purposes only.