Career Couldas, Wouldas & Shouldas

“𝘾𝙤𝙪𝙡𝙙𝙖. 𝙒𝙤𝙪𝙡𝙙𝙖. 𝙎𝙝𝙤𝙪𝙡𝙙𝙖.”

Those are three of the most expensive words in a career.

They usually show up years later.

When someone says:
• “I should’ve left sooner.”
• “I could’ve negotiated that offer.”
• “I would’ve pivoted if I knew this was possible.”

Hindsight is brutally honest.

And it almost always reveals the same thing:

You didn’t fail because you lacked talent.
You failed because you didn’t have guidance at the right moment.

Which brings me to a myth I hear constantly.

Experience used to matter more.

You think:

“All they care about now is keywords and ATS.”

True.

But before?

All they cared about was:
– Who you knew
– Where you went to school
– Your zip code

Technology didn’t kill fairness.
It exposed how biased things already were.

And while we’re on it, careers also used to be linear.

You think:

“My parents worked one job their whole life. Careers were stable.”

Yes.

And also:
– Fewer industries
– Fewer choices
– Fewer second chances

Today’s careers zigzag.

Not because things got worse.
Because you’re allowed to change directions now.

Here’s where most “coulda, woulda, shoulda” moments come from:

• Staying too long in a role that stopped growing you
• Assuming your resume would speak for itself
• Waiting for clarity instead of creating it
• Not negotiating when you had leverage
• Not repositioning when the market shifted
• Trying to “figure it out” alone under pressure

By the time regret shows up, the cost is already paid.

That’s why I always say:

The most valuable career decision isn’t your next job.

It’s when you decide to get expert eyes on your strategy.

Not after you’re burned out.
Not after you’re underpaid.
Not after you’re stuck.

But before the “shoulda” phase begins.

Because careers don’t derail from one bad move.

They drift quietly from unexamined ones.

Ready to improve your career search? If you’d like, we can hop on a quick call and I can walk you through how I can help.
You can book a chat with Matt at 👉 https://calendly.com/mjwcareers and get you some Matt Magic (client’s words, not mine).