Four Career Mistakes Sales Professionals Regret

No matter where you’re at in your sales career, it’s not too late to avoid these common regrets.

Regret can make your life miserable. It can even force you to leave a career you once loved. After coaching and consulting hundreds of sales professionals and business owners, I’ve met plenty of successful people who wish they could do a few things differently.

side profile of businessman standing outside

Across this diverse group of people, these four regrets have come up over and over again:

  • Not asking for help
  • Keeping unnecessary relationships
  • Worrying
  • Jealousy

Interestingly, these common regrets aren’t tactical mistakes—they’re all about mindset! Some professionals take years (or decades!) to realize they’ve been holding themselves back. That means years of not living up to your potential and missing out on opportunities—and someday saying, “I wish I had known better ten years ago!”

They say wisdom is learning from others’ mistakes, so let’s look at each one. Think about how you can change your mindset to avoid these and save yourself from regret!

Not Asking For Help

Too many people wait too long to ask for help running their business.  

Maybe you believe you should be able to figure things out on your own. Maybe you think your questions are stupid. Maybe you feel asking questions is silly, embarrassing, or weak.

But what’s more embarrassing—asking a bad question or having your business fail?

Ask for help. If you’re working with a prospect, it’s okay to not know the answer! 

Recently, I worked with a company who had a new salesperson. His client needed a solution, and the salesperson was pretty sure his company’s software was capable of providing it. So, he went ahead and sold them the software.

It turned out that what he sold didn’t cover the client’s problem. The company had to go back with their tail between their legs to explain that the client would have to pay more for an add-on package to get the functionality they needed.

This could have been avoided if he simply told his client, “I think we can do that, but I’d like to check with my team to be certain. Let me get back to you.”

Don’t let your ego get in your way of tapping into the resources that will help you succeed. Leverage your team’s knowledge. It’s not worth losing a deal just because you were too proud to ask for help!

Keeping Unnecessary Relationships

Many sales professionals will keep certain partners around for far too long. These people drain your energy, take up too much of your time, and aren’t really ideal partners. But you keep them in your book of business, because you feel like you “need” them.

This is the scarcity mindset at work. You don’t need them!

It can be hard to let relationships go, but you need to constantly evaluate your business relationships and ask if they’re a good match. This applies to inner circle relationships, referral partners, power partners, and even clients.

Don’t waste your energy, time, and effort to keep a less-than-ideal relationship going, when tons of other people can help you truly move your business forward.


Salespeople love to worry! They worry about closing a sale, losing a client, losing their job, their team being happy, a project coming to an end.

Believe me, I find myself worrying, too—from hitting annual growth goals to successfully onboarding new hires. But when I heard this phrase about worrying, it really struck me:

Worrying is like praying for something you don’t want.

I actually have this written down on a sticky note and stuck to my monitor! It’s so true.

Worrying is useless. It does nothing for you and nothing for your business.

If you’re worried about a situation, it’s a sign you need a plan. Instead of worrying, focus on forming a strategy on how you’re going to attack the situation. Setting goals and planning how you’ll achieve them is the best way to overcome worry!


Many professionals don’t fully come to regret jealousy until later in their careers. Jealousy has an interesting effect on your business.

Jealousy is closely related to the scarcity mindset. Someone else hits their goals or has a big win. Somebody goes on an amazing vacation or grows their business into a huge success. You see it, and say, “I’ll never be able to do that,” or, “Why don’t I get to do that?”

Success is not a limited resource! But jealousy makes us see other people’s success negatively, making us feel like there’s not enough room for us to succeed.

The way to get past jealousy is to use the success of others as a positive driving force. Instead of asking, “Why do they get to have an awesome vacation,” tell yourself, “If they can, I can too!” 

Of course, I’m realistic with myself. I know I can’t go out and win the Tour de France! But if someone else’s accomplishment is truly impossible for you, there’s no reason to waste time being jealous about it—just be happy for them, be inspired and move on.

Use other people’s success as motivation to catapult your business. If they can do it, chances are you can do it too—you just need to set your goals, identify your challenges and opportunities, and make a plan.

“If they can, I can.” This phrase has been a mantra for me for years. Don’t get jealous of other people, when you can use their success to drive you forward!

Avoid Regret—Change Your Attitude!

Ask for help, curate your relationships, stop worrying and ditch the jealousy. You’ll be more flexible, more open, more positive, and ultimately more successful—and you won’t be saying, “If only I could do it all over again!”

Even the best sales champions need to be vigilant about their attitude. Often, the best way to get your head back in the game—or energize your sales team—is to work with a professional sales coach. If you’d like to learn more, drop me a line.

Until next time—go sell some stuff!


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