What I Wish More People Understood About the Emotional Side of Career Transitions

By Kendra Stearns Drozd, Bluffton, SC

The Part No One Talks About in Exit Interviews

When I left Kraft Foods to become an executive recruiter, people congratulated me on the new opportunity. When I stepped away from recruiting to focus on raising my daughters, people nodded and said supportive things. But almost no one asked about the part that actually kept me up at night: whether I was making the right choice, whether I’d regret it later, whether I was somehow letting down the version of myself who’d worked so hard to get into Kellogg and land that brand manager role.

Career transitions get framed as strategy decisions. We talk about work-life balance, compensation, growth opportunities. All of that matters. But the emotional weight of changing course, especially when you’ve invested years building expertise in one direction, rarely gets the attention it deserves.

It’s Not About Doubt, It’s About Grief

I’ve had conversations with dozens of professionals over the years, first as a recruiter and later through my work in Stephen Ministry, where I provide confidential emotional and spiritual support to people facing life crises. One pattern shows up again and again: people going through career transitions often experience a form of grief, even when the change is positive.

You’re not just leaving a job. You’re leaving an identity. The relationships you built. The rhythms you knew. The version of yourself who showed up in that role every day.

When I moved from advertising to business school, I grieved the creative energy of working on campaigns. When I transitioned from Kraft to recruiting, I missed being close to the consumer research work I’d loved, like those in-home studies where I watched families navigate their daily meal routines. When I stepped away from full-time work after my third daughter was born, I grieved the professional momentum I’d built.

None of those transitions were mistakes. But pretending they were purely logical choices would be dishonest.

The “Fake It Until You Make It” Trap

There’s a poem my tennis coach made us memorize when I was growing up. It starts, “If you think you are beaten, you are; if you think you dare not, you don’t.” I’ve carried that mindset my entire life, and it’s served me well in competition and in moments when I needed to push through self-doubt.

But that approach has limits when you’re navigating a major life change. Sometimes “fake it until you make it” just means you’re suppressing real feelings that need to be acknowledged. You can believe in your decision and still feel scared. You can be excited about what’s next and still mourn what you’re leaving behind.

The turning point for me came when I stopped treating my feelings as obstacles to overcome and started treating them as information. Anxiety wasn’t a sign I’d made the wrong choice. It was a sign I cared deeply about getting the next chapter right.

What Actually Helps

After walking through several of my own transitions and supporting others through theirs, a few things have proven genuinely useful:

Give Yourself Permission to Be Ambivalent

You don’t have to feel 100 percent certain. You don’t have to make the case that your old role was terrible or that your new path is perfect. Both things can be true: your last chapter mattered, and it’s still time to turn the page.

Talk to Someone Who Isn’t Invested in Your Decision

When I was weighing my move into recruiting, my husband was supportive but naturally invested in how the choice would affect our family. My former colleagues at Kraft had opinions shaped by their own career paths. What I needed was someone who could just listen without an agenda.

That’s part of why I became a Stephen Minister. Sometimes people need space to process out loud without advice, without judgment, without someone trying to fix it. One of my care receivers and I worked together for about five years. Walking beside her during her most difficult times taught me how powerful it is to simply be present for someone.

Expect the Adjustment to Take Longer Than You Think

When I joined Bloom, Gross & Associates, the work itself came naturally. I’d spent years in marketing, I understood the CPG world, and I enjoyed connecting with people. But it took months before I stopped instinctively thinking of myself as a brand manager first. Identity shifts lag behind circumstantial changes.

Be patient with yourself during that lag. You’re not slow. You’re human.

The Long View

Looking back now, every transition I made opened up something I couldn’t have predicted. Leaving brand management led me to recruiting, which gave me flexibility as a young mother. Stepping away from full-time work gave me the space to get involved in Stephen Ministry, which has become one of the most meaningful parts of my life.

But I didn’t know any of that at the time. I just knew I was trying to make the best decision I could with the information I had, while managing a swirl of conflicting emotions.

If you’re in the middle of a career transition right now, here’s what I wish someone had told me: the fact that it feels hard doesn’t mean you’re doing it wrong. It means you’re doing something that matters. And that’s exactly the kind of thing worth feeling deeply about.

Share the Post: