What if the career you worked so hard to build is no longer the one you actually want? Executive coach and author Diana Bernal joins Jannese to talk about the cultural scripts holding us back, the framework for making a real career pivot, and why it is never too late to start from experience.
The First-Gen Career Script Nobody Warned Us About
If you grew up first-gen, you probably know the script. Go to school. Get a degree in something practical. Get the job. Stay loyal. Keep your head down. And whatever you do, do not complain — because you are lucky to be here.
Diana Bernal lived that script. A first-generation college graduate from Chicago, she made her way through DePaul University while working full-time after running out of money halfway through. She learned the corporate ropes in human resources, climbed the ladder in nonprofit fundraising, and set her sights on the senior vice president corner office. Then she got close — and realized it was not actually what she wanted.
“I would have seen myself as a senior vice president with a corner office,” Diana says. “And then eventually that wasn’t enough. That didn’t become fulfilling.”
Sound familiar? For a lot of us, the first crack in the script shows up right when we are supposed to feel like we have made it.
“We think we get this job and we go from accountant one to senior accountant to accounting manager, but we don’t stop to take stock to say — is that really the next thing for me?”
Signs You Are Autopiloting at Work (And Your Boss Can Tell)
Diana is not talking about a bad week or a rough quarter. She is talking about the slow drift that happens when you have mentally left the building but your body keeps showing up.
Here is what autopiloting actually looks like:
→ Shopping online during work hours when you should be focused
→ Showing up later and later every day
→ Zero interest in training, professional development, or industry news
→ Not caring about conferences, journals, or the things you used to care about
And here is the part that might sting a little: if you can feel it, your manager can feel it too. Diana shares the story of a friend’s son who was coasting at work, not excited, just getting through. His boss eventually pulled him in and asked point blank if he was happy there. He said no. And then he was let go — without anything else lined up.
“That’s why I think it’s really important for people once a year to take an assessment of their careers,” Diana says. “If you know you’re unhappy, you should be doing things behind the scenes at home to get yourself ready.”
How to Stop Letting the Sunk Cost Fallacy Keep You Stuck
Let’s talk about the thing that keeps so many of us frozen: the degree. The years. The idea that if you walk away now, it was all a waste.
Jannese knows this one personally — spending years as an engineer in a field she never truly felt at home in, as one of the only Latinas in the room. The sunk cost fallacy is real, and it is loud, especially when your family has sacrificed to get you there.
“You have to give yourself permission. This was what I wanted at the time. It gave me experience, exposure, and lessons. And now I’m looking for something else.”
Diana reframes it this way: every job, every skill, every hard year is a foundation — not a prison sentence. The pivot is not a betrayal of the degree. It is a use of everything you have already built.
And yes, that conversation with your mom might still be hard. But as Diana puts it: you do not need to ask permission to make decisions about your own life. Especially not at 41.
The Three-Part Framework for a Career Pivot That Actually Fits
Diana’s book, Career with Intention, walks readers through a six-week process for getting clear on what they actually want. The framework has three pillars:
- Values — Get specific. Family as a value can mean working closer to home or it can mean making more money to put your kids through college. Dig into what your values actually look like in practice.
- Skills and Interests — Skills are what you are already good at, the things people come to you for without being asked. Interests are what lights you up. Find the overlap.
- Place — This one gets overlooked. Do you thrive in a small office or a big corporation? A city or somewhere quieter? The environment matters as much as the work itself.
When you put all three together, Diana says, a picture starts to emerge. And that picture is a lot more useful than just sending your resume into the void and hoping something lands.
You Are Not Starting Over. You Are Starting From Experience.
One of the most common things Diana hears from clients — especially women in their forties and fifties — is that it is too late. Too late to pivot. Too late to start something new. Too late to want something different.
Diana made her own pivot in her fifties.
“You are not starting over. You are starting from experience. You are starting from where you are, and you have all this great experience.”
The thing people regret most, Diana says, is not the risks they took — it is the ones they never tried. She wants to help people prevent regret. And that means testing the waters before the fear gets a vote.
She shares the example of a friend who was always drawn to real estate — going to open houses, helping people style their homes. They tried being a real estate agent for a year and realized it was not for them. But at least now they know. No regret hanging over their head at 65.
Grateful and Ambitious: Two Things You Can Be at the Same Time
Here is the cultural script that hits differently for first-gen Latinas: the idea that wanting more is ungrateful. That if you have the degree and the job and the benefits, you should be satisfied. That ambition is somehow disrespectful to everything your parents sacrificed.
Diana has a response to that:
“We can be grateful and want more at the same time.”
Gratitude and ambition are not opposites. You can honor where you came from and still choose something different for your future. You can love your parents and not repeat their path. And you definitely do not need their permission to want more — even if that conversation is going to be uncomfortable.
Diana’s advice: do your exploration quietly at first. Know who your cheerleaders are and who your critics are. Make the decision before you announce it to the room.
Side Hustle, Career Pivot, or Both? Here’s How to Know
If you are feeling that pull toward entrepreneurship — or just wondering whether your nine-to-five is the problem or if you just need a different nine-to-five — Diana has a simple answer: test it.
“Start with what you know,” she says. “Look to what you already do and test it on the side. Keep your day job. But start testing.”
Then comes the real validation:
“You have to see who is going to pay you beyond your family and friends. You need a stranger to pay you to validate that there is potential here.”
If you can get someone who does not love you to pay for your thing, you might have a business. If you can only get your mom and your best friend to buy it, you have a passion project — which is fine, but it is not a business yet.
And if entrepreneurship is not for you? That is also a valid answer. Diana is not here to convince anyone. She is here to help people figure out what is actually right for them.
One Exercise to Try Right Now
If you take nothing else from this episode, take this: grab a journal and answer two questions.
→ What do I want MORE of in my career?
→ What do I want LESS of in my career?
That is it. Diana says if you do this with any consistency, what you are actually seeking starts to get clear, fast. Less administrative meetings. Less commute. More autonomy. More creativity. The pattern shows up if you let it.
Key Takeaways
- Autopiloting at work is not invisible — your manager can feel it too. Get ahead of it.
- The sunk cost fallacy keeps us stuck. Your past experience is a foundation, not a life sentence.
- Career clarity comes from the overlap of values, skills and interests, and place.
- It is never too late to pivot. You are not starting over — you are starting from experience.
- Gratitude and ambition are not opposites. You can be both.
- Test your side hustle idea with a stranger. If they will not pay, it is not validated yet.
- Journal on what you want more of and less of. Do it consistently. The picture will emerge.
Resources Mentioned
Get Diana’s book Career with Intention: https://bit.ly/4cp2Etu
Follow Diana on Instagram: @diana.bernal.inc
Diana’s website: https://www.dianainc.com
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