Elevating Ambitions: The Art of Making Bold Career Moves

Elevating Ambitions: The Art of Making Bold Career Moves

It's been over two years since I took my last flight in an F-16 and transitioned from pilot to entrepreneur.

What a wild ride it has been!

While I occasionally miss the kick-in-the-pants flying, running a business has been a different kind of thrill.

I'm often asked, "What advice do you have for someone who wants to make a similar career shift?".

So, in this installment of “Inverting Your Mindset,” I’ll share my process for making big, bold career moves while keeping your inner critic at bay.

Read time ~4 min. Ready? LET’S DO THIS!


Start With a Personal Audit

Conducting a personal audit is the first step to making any major career change.

Ask yourself some tough questions (take your time with these):

  • What do you want your life to look like day-to-day?
  • Do you crave more freedom and flexibility or prefer structure and routine?
  • Do you want to make an impact, get creative, or build something new?
  • What are your financial goals and expectations?

The exercise will help you align your career aspirations with your values, interests, and passions.

I highly recommend taking your time on this. Really dig deep, do some soul-searching, and don't let your inner critic dismiss anything.

Tap into Your Passions

When you tap into your passions, you open yourself to possibilities beyond what society dictates you should do.

Reflect on moments when you felt most alive and enthusiastic. Pinpoint the common themes across your most meaningful experiences.

Look for ways those passions can translate into a viable career or business.

With some creativity, you can monetize any passion or area of interest in today's creator economy.

You may need to start small with a side project but remain open to where it may lead. Even part-time, passion-based work can be incredibly rewarding.

Don’t Forget the Soft Skills

Your soft skills will differentiate you from others with similar experience and allow you to provide unique value in any role or endeavor.

Some examples might be your adaptability, work ethic, leadership abilities, communication style, etc…

When making a career transition, it’s important to take stock of all your skills, not just technical proficiencies.

Identify the Gaps

Identify any skill or knowledge gaps between your current and your desired state.

For skills gaps, consider ways to develop the required competencies through classes, certifications, mentoring, job shadowing, or volunteering.

Building skills and knowledge takes time, so be realistic yet optimistic and avoid feeling overwhelmed.

Find Your Wingmen

When making a career transition, you don't have to go it alone.

Reach out to your network and see who's willing to help.

Start by making a list of all your connections. The list might include friends, family, coworkers, supervisors, mentors, and former classmates.

Next, think about who in your network could be an asset.

  • Who has key transferable skills to share?
  • Who has industry expertise relevant to your new path?
  • Who can connect you to new opportunities and people?

When reaching out, be transparent about your career goals and how you think your contact could help.

But don't only ask directly for help. Instead, seek advice and meaningful connections. Ideally, you will nurture these relationships well before you need to ask for anything.

Sometimes, the most unexpected people in your circle want to see you succeed and will go out of their way to help make it happen.

Tame Your Inner Critic

A big change or pivot is one of those times when our Inner Critic tends to get riled up.

But remember, those negative inner thoughts aren't facts. They’re simply interpretations of your past experiences.

When you hear that voice chime in, pause, take a deep breath, and climb to a safe Thunderbird cruising altitude of 30,000'.

From this altitude, we can view our inner critic from a different perspective, which helps us identify, label, and change its dialog.

Ask yourself:

  • What does your inner critic say when you're about to step out of your comfort zone?
  • Whose voice does it resemble—a parent, a boss, or perhaps some external expectation?

Write these thoughts down and draw what your Inner Critic looks like.

I learned that when you give your Inner Critic a physical form, it removes some of its power over you because you can view it as a separate entity.

This separation creates a space where you can choose whether or not to listen.

Bringing it Home

It's natural to feel uneasy when facing unknowns in a career transition.

Be patient with yourself if things take longer than expected. Stay focused on your goals and chip away at your plan each day.

Even if this is something brand new, don't let your Inner Critic convince you you're not cut out for it.

It’s perfectly OK to be a beginner and not know things when starting something new. Give yourself the grace to take time to learn and to make some mistakes.

Consciously reframing that Inner Critic to say, “I’m new and learning,” rather than, “I’m not smart enough or good enough to do this thing,” can be a huge turning point in finding the courage to make a big pivot.

Before you know it, you'll be ready to leap into an inspiring new career!

Until next time.

Your Wingman,

EMBRACE YOUR INNER BADASS

I recently announced my “Badass Masterclass: A Fighter Pilot's Guide to Building Courage & Conquering Your Inner Critic.”

This class will provide you with the direct guidance you need to reframe these thoughts and will lead you into the world of success and opportunity that awaits on the other side.

You’ll join a community of other badasses realizing their potential!

That promotion you’re eyeing? That exciting business opportunity?

They are NOT meant for someone else. They are meant for you.

But you must be willing to take action even when it feels scary and uncomfortable.

Be the first to know when enrollment is open.

Join the waitlist HERE!


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In early 2022, I left active duty to found Upside Down Dreams.

Interested in my keynotes and workshops?

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chris conca

Project Development Coordinator at ASTRIS CONSTRUCTION LLC

9mo

No time limit on Patience

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Doug Ronald

Imagine your work aligning with your life goals, not the other way around. I help clients uncover what success, freedom, and fulfillment look like for them and build a clear path to achieve it. | Career Ownership Coach

9mo

Great perspective! So many are simply afraid to embrace their dream and "go for it"!

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Michelle “MACE” Curran

Professional Speaker, Thunderbird Pilot ‘19-‘21, Combat Veteran, Fighter Pilot, Author, Outdoor Enthusiast ➡️ I can help you get unstuck by empowering you to face your fears and take calculated risks ➡️ Let's connect!

9mo

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