How to Build Confidence When Reinventing Yourself After 40

A personal reinvention — even a small and superficial one — can teach you everything you need to know to take on big, bold, and purposeful career pivots in midlife.

Personal and professional reinventions at any stage of life are more interconnected than we think, and one of the biggest factors keeping us from taking action is thinking we need to somehow become confident first.

But the truth is, confidence is never a requirement for successful and meaningful reinventions.

After a few successful pivots, I’ve learned that confidence is always earned. 

It’s built along the way. It’s a byproduct of taking action. It’s an end result, not a starting point.

Pivots are about identifying who you want to be in a given season of life and determining how you’re going to show up as her today and every day until you become her.

I accidentally learned this much earlier in life and in a pretty unexpected way.

Confident Reinvention in Your 40s

My First Reinvention: The Straight-Hair Girl

Growing up with wavy, very frizzy hair, not only did I not have one photo I didn’t cringe at, but I was very self-conscious.

My mom, who’s a saint, tried hard to learn how to style my hair, but she would always end up just brushing it, which always ended in a tearful commute to school — iykyk.

I was so unhappy with my appearance that by age 15, I decided I would be a straight-haired girl. 

I think this was my first conscious reinvention, although I didn’t even know the word reinvention back then.

I didn’t know what it would entail to become her, how much work it would be, or how difficult it would be to learn to straighten my hair.

I just knew I was going to be her. I was going into my junior year of high school as the girl with neat, straight, non-frizzy hair, every single day.

My frizzy, puffy, messy (to me) hair days were over for good (until my 30s of course, when maturity allowed me to embrace my curls from time to time)

And confidence? Why would I have any if, in 15 years, there was zero evidence of a single good hair day?

I was not relying on confidence to take that on. Just a really, really strong desire to make it happen and a crystal clear vision of what it would look like.

While some girls show up as straight-hair girls thanks to genetics, what did it mean for me to show up as a straight-hair girl before I was one?

It meant practicing straightening my hair every chance I got (sometimes multiple times a day).

It meant failing at it often.

It meant crying to my friend on the other side of the phone.

It meant burning myself or my hair with various tools.

It meant sore arms and wrists from doing it so much.

It meant going to bed later or waking up earlier to get it done.

Eventually, I was seeing results. My hair was looking more acceptable to me. It was looking more like the straight-haired girl I was envisioning. And I was becoming much more proficient at it, too.

Soon, friends, tennis teammates, and sigh finally, boys were complimenting my looks — shallow, I know, but this is high school we’re talking about.

Confidence was nowhere to be found when I started, but it sure started showing up as I got more skilled and consistent at achieving my new look.

Confidence peaked when I was no longer a girl who straightened her hair — I was a straight-hair girl.

Ever since, I have applied the same rigor to every other pivot or reinvention I’ve gone through personally and professionally, including my current one. 

The common denominators each time were the same: 

• A powerful desire and/or why. 

• A crystal clear vision. 

If those two were present, I knew, without a shadow of a doubt, I would pivot successfully even if I didn’t have the whole plan or steps mapped out.

If they weren’t there, it was only a matter of time before I would realize that what I was chasing wasn’t truly for me.

Confidence didn’t come first — it came through the commitment.

My Second Reinvention: From TV to Project Management

Fast forward a couple of decades. I had built a successful television career — exciting, fast-paced, and incredibly demanding. But somewhere along the way, it stopped feeling aligned.

I was burned out. I loved what I did, but the demands of the industry were sucking the life out of me.

I started to crave a different kind of impact — one with more structure, more growth, and more personal meaning.

So I set my sights on pivoting into project management. Again, I had no formal confidence — just a strong pull toward a new path.

And once again, I had to become the version of me I envisioned:

• I woke up early to study before work

• I joined and volunteered at my local PMI chapter

• I read everything I could about becoming a PM

• I immersed myself in the identity before I ever held the title

A year later, I landed a job as a Marketing Project Manager, and two years after that, I earned my PMP certification.

Some people were project managers because they already were. I became one because I chose to be — long before anyone paid me to do it. 

That’s the power of intentional reinvention.

My Third Reinvention: From Corporate to Entrepreneur

That’s the midlife reinvention I’m currently in. As I write this, I’m actively in the messy beginning of it. And I’m doing it somewhat publicly this time.  I want to be able to share, in real-time, the challenges, the wins, the setbacks — the good, the bad, and the ugly. 

Stay tuned for more on this one in future content. 

So, how do you build confidence when you're in the middle of a pivot?

Not the glossy version. Not the “I totally know what I’m doing” version. But the kind that keeps you moving forward even when you feel like an impostor?

Here’s what I’ve learned — both as a straight-hair girl in high school and a midlife woman reinventing her career and life from the inside out:

1. You don’t need confidence to start — just a clear vision.

What matters most is why you’re doing it — not how good you are at first. You don’t have to believe in your ability yet. You just have to believe it’s worth figuring out.

2. You’re not starting from scratch — you’re starting from wisdom.

Even if your new path feels unfamiliar, you are not. You’re bringing decades of grit, discipline, emotional intelligence, and resilience with you.

That’s your launchpad — not your limitation.

3. Identity is built through action.

You become the person you want to be by doing what that person would do — Straightening your hair every day, studying before work, howing up scared. 

Identity follows behavior, not the other way around.

4. Confidence grows through evidence.

Every time you take a small brave step, you build internal proof: “I can do this.” It stacks. Slowly at first — then exponentially.

Your confidence is just your brain learning to trust you.

5. You get to reinvent yourself as many times as you need.

Reinvention isn’t a crisis. It’s a sign of growth. You’re allowed to evolve. You’re allowed to want more.

You’re allowed to become someone you’ve never been before.

Final Thought

If you’re in a season of change or starting something new — please don’t wait for confidence.

It’s not a signal to begin. It’s a reward for showing up anyway. You’re not too late. You’re just in the middle of becoming.

And that’s a beautiful place to be.