How to Fix Your Sales Mindset Before It Wrecks Your Pipeline

EP21 | Will Aitken

Rising From Self Doubt to Sales Success

Will Aitken isn’t just a name in sales—he’s the name popping up on your LinkedIn feed, in your head, and probably on your TikTok scrolling sessions.

But long before the punchlines and polished skits, he was a struggling AE wondering if he even belonged in sales.

In this raw, hilarious, and insight-rich episode of I Used To Be Crap At Sales, Mark Ackers sits down with the keynote speaker, meme lord, and now author-to-be to unpack the career that almost wasn’t.

This conversation is a masterclass in self-awareness, ego-checking, and what it really means to become coachable. If you’ve ever questioned your place in sales—or how to get better when you’re stuck—this one delivers.

Watch The Episode:

Or listen on Spotify or Apple here.

Will's 5 Top Tips For Levelling Up Your Sales Career:

1. Stop Blaming, Start Owning

The Challenge:

“I was on a yo-yo—230% one quarter, 11% the next—and I blamed everything but me.”

The Insight:

Will admits he used to point fingers at his manager, territory, and product. But the real change started when he turned the mirror inward and asked: What am I actually doing about it?

The Quote:

“Excuses are toxic... I knew I had to take accountability because blaming others wasn’t getting me anywhere.”

The Fix:

Accountability became Will’s unlock. He stopped waiting for better conditions and started asking better questions: What can I control today? What am I doing when no one’s watching? That shift laid the foundation for growth—and a career revival.

2. Ego Is the Enemy (Even When You’re Winning)

The Challenge:

Success is great—until it makes you think you don’t need help.

The Insight:

After becoming the first rep at his company to hit quota consistently, Will admits he let his ego creep back in. The wake-up call? Not getting the promotion he felt entitled to.

The Quote:

“The reason I left wasn’t failure—it was my ego. I thought I deserved more, and when I didn’t get it, I took my ball and went home.”

The Fix:

Will reframed the moment as a signal, not a slight. It reminded him how quickly ego can derail progress.

The antidote?

Staying coachable, curious, and open to being wrong—even when things are going right.

3. When You’re Coachable, Everything Changes

The Challenge:

Will knew he needed a reset—but didn’t know how deep the change needed to go.

The Insight:

A manager mentioned Gap Selling and The Science of Sales.

Will devoured them both. Not just to prep for the job—but because he finally understood sales was a skill he could learn. And that he had so much more to learn.

The Quote:

“I didn’t care about being the best anymore—I cared about being competent.”

The Fix:

He leaned into feedback, started recording and analysing his calls, and worked with managers who challenged him. He didn’t just improve—he transformed.

The shift from performer to student became the fuel for lasting success.

4. Need for Approval? Say Goodbye.

The Challenge:

Validation was everything to Will—likes, leaderboard spots, promotions. But it made him avoid tough questions, both with himself and with prospects.

The Insight:

Chasing approval leads to shallow conversations. Real sales success demands courage—the kind that challenges, disqualifies, and digs deep.

The Quote:

“When you don’t get to the truth, you can’t help. And when you chase approval, you end up with a pipeline full of lies.”

The Fix:

Will stopped trying to look successful and focused on being useful. He began asking hard questions, pushing past surface-level conversations, and prioritising real outcomes over momentary praise.

5 More Things You’ll Learn From This Episode

1. The Real Reason You Might Be Struggling in Sales
   Will’s candid reflection on what happens when you work remotely, lack structure, and aren’t honest with yourself.

2. How Social Media Can Wreck Your Sales Mindset
   The dopamine trap of likes, engagement, and chasing validation—and how Will clawed his way back from it.

3. Why Journaling is a Secret Sales Superpower
   It’s not fluffy. Will shares how daily reflection sharpened his self-awareness and kept his ego in check.

4. The Sales Lesson Hidden in Failing University Plans
   From aspiring aerospace engineer to events management major (for, let’s say, creative reasons), Will’s detour proves your degree doesn’t define your destiny.

5. The Most Fulfilling Work Will’s Ever Done—And It’s Not What You Think
   Hint: it’s not content, comedy, or cash. It’s coaching, and helping others level up by being the kind of guide he once needed.

Listen To The Full Podcast Here: