In the opening scene of Tootsie, Michael Dorsey—played by Dustin Hoffman—sits in a casting office, begging for a role. He tells them he can play young, old, tall, short, anything they need. They tell him no.

He auditions again. And again. And again. Each time, the answer is the same: No.

Finally, in desperation, he reinvents himself as Dorothy Michaels. He lands a role he never expected, on a soap opera that never would have hired him. What was supposed to be a short-term gig turns into a long-term contract.

I have watched this movie a dozen times, and somewhere along the way, I began to see my clients in it.

The Tootsie Syndrome: What Executive Career Coaching Reveals About Being Passed Over

I meet executives every week who are convinced they are getting "no" for reasons entirely out of their control. They feel they are too old, too young, too experienced, not experienced enough, too corporate, or too entrepreneurial.

If you feel you are being passed over because of some "ism," here is a hard truth: If a company does not recognize the value you offer, do you really want to work for them anyway? An organization that cannot see past the surface is likely not a place where you will thrive. You might eventually be thankful they selected themselves out of your future.

But there is another truth: Sometimes the "no" has nothing to do with who you are, and everything to do with how you are showing up.

If you are ready to stop interviewing for roles that never materialize, here is how to stage your own reinvention.

1. Stop Fighting What You Cannot Change

You cannot make yourself younger. You cannot un-live your twenty years of experience, and you cannot erase your background or your journey.

And why would you want to?

Companies chasing rapid growth need leaders who have been through the fire. Young, hungry startups need skilled advisors who have already survived the mistakes they are about to make. Global enterprises need executives who understand entirely new markets.

Your perceived liability is actually another company’s competitive advantage. Your job is to find that organization.

2. Executive Presence Starts With How You Show Up Physically

I will not tell you that looks don't matter. They do. Not because hiring managers are shallow, but because leadership is presence. And presence is physical.

Join a gym, take a class, or start walking. The goal is not just to drop a few pounds—it is to manage the cortisol that comes with job-search anxiety, boost your energy, and project the vitality that boards look for in a leader.

While we are on the topic of appearance:

Hair: If you color your hair, have a professional handle it. Box dye reads as "desperate" in a way you cannot afford.
Wardrobe: If your weight has fluctuated significantly, invest in a new suit. An ill-fitting outfit signals that you lack attention to detail.
Grooming: Trim the beard. File the nails. Look like someone who expects to be seen.

3. Gratitude as a Job Search Strategy

During my time in sales, I learned a hard rule backed by sales statistics: it often takes twenty no's to get one yes. Rejection was not a failure; it was just a necessary step toward the client who would eventually agree.

Your job search is no different.

Every interview you do not land is a chance to refine your approach. Every dead-end conversation is practice for the one that matters. Every "no" is simply data. Collect it, learn from it, and keep moving forward.

4. Save the Day: Build Your Executive Value Proposition

Mighty Mouse had super strength and X-ray vision. What is your superpower?

Sit down and write out your SHARE stories: Situation, Hindrance, Actions, Results, and Expertise. These are not just standard resume bullets—they are tangible proof that you are the hero this organization needs.

Next, use your X-ray vision. Look past the generic job description to uncover what the employer is genuinely struggling with. If it is a publicly traded company, read their earnings call transcripts. Study their competitors and talk to former employees. Find their pain points and address them directly in the interview.

If your confidence is low, ask five trusted colleagues: What am I best at? Write down their answers and read them every morning. And if your resume is outdated, get it professionally rewritten. A certified writer is trained to see your unique gifts much more clearly than you can see them yourself.

5. Personal Branding: Give Them Something to Talk About

The days of simply mailing your resume to a job ad are over. Your document must now accomplish three things simultaneously:

Survive the automated Applicant Tracking Systems (ATS).
Pass the recruiter's six-second visual scan.
Compel a busy executive to pick up the phone.

If your resume reads like a boring job description, it will be ignored. If it has a typo, it will be trashed. If it does not tell a clear, coherent story about how you create value, it will be forgotten. Treat your resume like the marketing asset it is.

6. Stand Out With Deep Research

An actor who shows up knowing everyone's lines gets the part. An executive who shows up knowing the company's deepest struggles gets the offer.

Spend at least six full hours researching the organization before your interview.

Review guides on Glassdoor to understand their interview culture and salary ranges.
Check Google News for recent press releases and customer sentiment.
Search LinkedIn for employee profiles and thought leadership posts.
Review annual reports to pinpoint strategic priorities.

Walk into the room knowing more about them than they know about themselves. Use that knowledge to prove you are the only logical choice.

The Bottom Line

At the foundation of your job search is a person who makes a difference. Whether you are twenty-five or sixty-five, you bring something no one else can.

If you are new to the workforce: You bring fresh ideas and novel insights.
If you are a seasoned leader: You have survived downturns and disruptions. You know what works. That is not baggage—it is ballast.

And if being a traditional employee no longer serves you? Do a Tootsie. Reinvent yourself. After all, Dorothy Michaels only took the role because she had no other options, and it turned into the opportunity of a lifetime.

Anne-Marie Ditta is an executive career coach and globally recognized content developer focused on helping mid-level managers and C-suite executives plan and execute rewarding moves at every phase of their careers. You can learn more at firstimpressioncareerservice.com or schedule a complimentary consultation.

Ready to reframe your story? Explore our Executive Coaching Services →

Too Old or Too Experienced? How Executive Career Coaching Turns Your "Problem" Into Your Superpower