This Career Catch-22 is Bulls**t (Here's How to Break It)

A special thanks to our sponsors:

Sick of watching average executives win roles you deserve? Get the best deal we've ever offered on my time! Register now

C-Suite Resumes: Need a personalized executive resume strategy? Book a 1:1 call with Jessica Hernandez's expert team now.

Sponsor This Newsletter

👋🏻 Jacob here.

Happy Halloween.

My son is the Very Hungry Caterpillar this year, so I'd like to finish work early. Please send me your best Halloween pics to help me through it. I'll give the best submission a free pass to my 8-hour workshop in November.

Now, let's talk about the infamous career catch-22 — You can't get experience without the job, and you can't get the job without experience.

Some will consider expensive MBA programs and snatch up new badges and certs to bridge the gap—but they're not worth much when propelling you into more senior positions without the right narrative and psychology to back them up.

Here's what everyone gets wrong: They think updating their resume and LinkedIn profile is enough. While important for positioning and to attract the right inbound, they solely rely on optimizing keywords, pray to the ATS gods, and wait for recruiters to magically understand their potential.

Spoiler alert: That's not how this works. That's not how any of this works for leaders.

You can't just sit there waiting to be discovered like some LinkedIn influencer's fairytale Christmas land.

You need to create the conversations about your growth. You need to control the narrative. You need to build your pipeline.

Variations of this approach also apply to senior leaders interested in expanding their remit or climbing to CEO / board roles. It's about creating, not finding — about alignment on your mutual vision, not sharing an impressive past.

This requires rhetoric and persuasive conversation.

The real mindfuck?

Your CREDIBILITY won't save you.

Being the LOGICAL solution won't save you.

Because here's the truth: logically, hiring you doesn't make sense.

Your credibility? It's only sometimes applicable to where you're going next.

There are more capable, more qualified, and more competitive hires available (at least perceivably, from the position of the hiring managers that demand recruiters to find them).

Your perfectly crafted list of transferable skills means nothing if you can't make everyone throughout the process FEEL that you're the right choice. This requires EQ and emotional mastery, which few possess.

You must create the opportunity and take ownership of the hiring process — continuously building momentum, advocacy (champions), and leverage during the "sale."

Remember: When a hiring manager takes a "chance" on someone without traditional experience, their ass is on the line. You need to make them your advocate, not your evaluator.

Startup sellers understand how difficult it is to make a deal with an intelligent decision-maker when the company they represent has yet to have a known reputation, brand awareness, product/market fit, etc.

Transforming your career is a similar struggle.

Here's the psychology hack that most career coaches don't seem to understand:

You must make it the hiring manager's idea to hire you BECAUSE you're different, not despite it. You must make it their idea—by setting the stage with your rhetoric.

Try this: "You strike me as someone interested in change, or I wouldn't be here today. You must have a good reason for that. What about my experience excites you most? Do you see us thinking about the team challenges differently together?"

Reframe.

You've repositioned your "lack of direct experience" as innovative thinking on their part.

We've used this approach to win board seats, promotions, CEO positions, and tricky cross-industry transitions while securing MORE compensation vs lateral or reduced comp.

It's a big deal.

Persuasive lines of questioning are necessary to create the most substantial opportunities for yourself—and to not get bogged down by the limitations that stop others.

Take your shots, and find the people who believe in you and think differently from the status quo.

Stay fearless, friends.

See you next week.

P.S. Want to master these psychology hacks and learn the exact language patterns that helped my clients land roles and compensation levels above their current positions?

Join me for my upcoming 8-hour intensive workshop this November. Early bird pricing ends today.