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Kristen Shepherd getting ready for a job interview

If I Could Help One Person โ€” Part Twenty-Seven

Still Standing

Getting ready for another interview after being sidelined for two years.

NewSobrietyIf I Could Help One Person ยท Part 27

If I Could Help One Person โ€” Part Twenty-Seven

Still Standing

Six interviews. No offer. A relationship tried for the fourth time. Financial pressure building. And still, somehow, getting dressed and going back in.

By Kristen Shepherd  ยท  April 19, 2026  ยท  8 min read

I knew when I came back that it would not be easy.

I was vibing with Florida. I really loved it there โ€” the water, the bridges, the wildlife. Some mornings I would just stand at the edge of the water and feel, for the first time in a long time, like I was exactly where I was supposed to be. It was amazing. Some days, I am still not entirely sure why I left.

Well. I know why I left.

A young woman passed away, and I wanted to help her father. That is the honest answer. That is the whole answer. I came back because grief called and I answered, and I do not regret the impulse โ€” only some of the consequences.

What I did not fully account for is what it is like to live with someone who is all-consumed in grief. There are a lot of lows to be dealt with. A lot of masking. A lot of chaos that does not announce itself โ€” it just appears, and you navigate it, and then you do it again the next day. I see it all more clearly now than I did when I made the decision to come back. At this point, I choose to take it one day at a time.


And then there is the other thing, the thing I keep circling back to in my quieter moments: this relationship has never worked before. Not once. We have tried living together three times before this โ€” three separate attempts, three separate endings. So the honest question I have to sit with is: why would it work this time, under more stressful circumstances than any of the previous attempts?

I do not have a clean answer. I think the hope is that grief changes people, that shared difficulty creates something new, that this time is different in ways that matter. Maybe it is. I genuinely do not know. What I know is that I am here, and I am trying, and I am watching carefully.


Meanwhile, financial stress is looming.

My independence has been in hibernation for two years. That is not a small thing to say out loud. Two years of not earning, not building, not having the particular kind of freedom that comes from your own income. I did not fully understand how much of my sense of self was tied to that until it was gone.

I have had three interviews in the last week. Six total since I started this search. And no offer.

I used to be so confident when I interviewed. I knew, walking out of the room, whether I had nailed it. I could read the energy, I could feel when I had connected, I could tell when the job was mine. That certainty was not arrogance โ€” it was earned. I had a track record. I knew my value. I walked in like someone who knew her value.

Now, six interviews in and no offer, I have to say: my confidence is shaken. My job skills feel rusty. My life feels uncertain. And the version of me who walked into rooms like she owned them feels very far away from the version of me who is sitting in a car in a parking lot, doing a last check in the rearview mirror before walking into another interview, trying to remember who she used to be.


I am fifty-something. I have decades of experience. I have built things, managed people, solved problems that did not have obvious solutions. None of that disappeared. And yet the market does not always see it that way. There is a particular kind of invisibility that descends on women at a certain age in professional spaces โ€” a sense that your experience is somehow less current, less relevant, less valuable than a younger candidate's potential.

I feel that. I am not going to pretend I do not.

But I also know that feeling it and accepting it as truth are two different things. I am not done. I am not irrelevant. I am rusty, and rusty is fixable.


So I started this webpage.

In hopes of finding my community. My prayer is that this page will take off in popularity with other Gen X women โ€” women who are navigating the same complicated intersection of career uncertainty, relationship complexity, financial pressure, and the particular exhaustion of being strong for everyone around you while quietly wondering if anyone is going to be strong for you.

I want to make this my full-time job. I am not certain anyone is even reading. But I am writing it anyway, because the alternative is silence, and I have been silent long enough.

If you are reading this โ€” if you are in your 50s and starting over in some form, if your confidence has taken a hit, if you are in a relationship that has a complicated history, if the financial pressure is real and the future feels uncertain โ€” I want you to know that you are not alone in it.

I am right here with you.

Still standing. Still showing up. Still getting dressed and going back in.

This is Part Twenty-Seven of an ongoing series. If you are new here, you can start at the beginning โ€” or you can start right here. Either way, you are welcome.

Coming Next

If I Could Help One Person โ€” Part Twenty-Eight

The next chapter of Kristen's sobriety memoir. Check back soon.

Check back soon โ†’

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