Learning that mistakes might be the best career move you never planned (I hope)

 > Information Security, IT Management, Mentor >  Learning that mistakes might be the best career move you never planned (I hope)
0 Comments

I announced two weeks ago, that I in the job market after a short tenure at a company. I learned that there is a sentence that feels heavier than it should. “I’m back on the job market.” It lands with a thud, even when no one else reacts. It immediately invites a flood of questions. What happened. Why didn’t it work. Did I miss something obvious. Did I mess up. For people who take pride in their work, their reputation, and the long road it took to get where they are, that sentence can feel uncomfortably close to an admission of failure. Not because it actually is one, but because we have collectively decided that success is supposed to look like a straight line. Choose the role. Move forward. Keep climbing. Anything else feels like a step backward, even when it is not.

The part no one likes to say out loud is that sometimes you make a decision that looks perfect on paper and completely wrong in practice. The interviews go well. The opportunity checks the boxes. The title makes sense. The compensation aligns. Everyone smiles and says the right things. And then you start the job and slowly realize something is off. Not in a dramatic, headline grabbing way. Nothing that would make a great cautionary tale over drinks. Just a quiet mismatch. A cultural disconnect. A realization that what was described and what actually exists are not the same thing. Your gut notices before your brain wants to accept it, and that is when the internal negotiations begin. Maybe it just needs time. Maybe you are overthinking it. Maybe this is just what growth feels like. We tell ourselves all kinds of stories because admitting a mistake feels more frightening than sitting in discomfort.

There is a strange pressure that comes with seniority. The more experience you have, the more you feel like you are not supposed to get it wrong anymore. You are supposed to know better. You are supposed to see the red flags. You are supposed to have the wisdom that only comes with years in the field. So when something does not work out, it can feel less like a situational mismatch and more like a personal flaw. Logically I know that mindset is brutal and completely unrealistic, and yet I still feel it. Experience does not eliminate uncertainty, it just helps you recognize it sooner. Even seasoned leaders are still making decisions with incomplete information. The difference is not that mistakes disappear. It is that you become better at naming them.

What makes being back on the job market particularly uncomfortable is not the search itself. It is the vulnerability. It is the moment where you have to say, even if only to yourself, this did not work. That weighs on me heavier than it should. We rarely celebrate self awareness in careers. We celebrate endurance, staying power , grinding it out and/or pushing through. Yet there is a quiet kind of courage in recognizing that staying in the wrong situation simply to avoid embarrassment is not resilience, it is avoidance and sometimes the strongest move is choosing honesty over optics.

There is also grief involved, and that part often catches people off guard. I grieve for the future version of me that I imagined when I accepted the role. I grieve the excitement that I felt on my first day. I grieve the story I told myself about how this chapter was supposed to unfold. Letting that go can sting, even when you know it is the right decision. It is possible to be both relieved and disappointed at the same time. I hope all people are like that…not just me.

What rarely gets talked about is how much you actually learn during these moments. Success is comfortable, it reinforces what you already believe. Mistakes, on the other hand, are teachers with no chill… they force reflection, they ask uncomfortable questions, they make you get honest about what you truly value, not what sounds or looks good on LinkedIn. You learn what kind of leadership you need around you. You learn what culture really means to you. You learn what you are willing to compromise on and what you absolutely are not. Those lessons do not come from promotions or praise. They come from friction.

Being back on the job market also has a humbling effect. It strips away the illusion that any role defines your worth. Titles fade quickly when you are staring at a blank document updating your resume. What remains is your actual experience, your skills, your character, and the relationships you built along the way. I personally find that can be grounding in an oddly healthy way. You are reminded that you are more than your last position. You are the sum of everything you have learned, including the chapters that did not go as planned.

There is also something freeing about starting again with clarity. When you reenter the market after a misstep, you are not chasing shiny objects anymore. You are asking better questions. You are listening differently. You are paying attention to how leaders speak about their teams. You notice how organizations talk about security, technology, people, and accountability. You are no longer just evaluating whether you can do the job. You are evaluating whether you want to do it there. For me that shift matters more than I think most people realize or give thought to in this process.

Admitting you made a mistake does not make you unreliable. It makes you honest and tt shows maturity (at least that’s what I tell myself). It shows that you value alignment over ego. The leaders I trust most are not the ones who claim flawless career paths, they are the ones who can say, yeah, that job/project/initiative didn’t work and here’s what I learned. Those are the people who tend to lead with empathy because they have lived the discomfort themselves.

If you are back on the job market right now, quietly or publicly, you are not alone. More people are navigating this than they will ever admit. Some are doing it after layoffs, some after reorganizations and some after realizing the culture they walked into was not what they signed up for. Different paths, same emotional weight. I want to stress to everyone in the same market…none of it is a reflection of your value as a professional or as a person.

Careers are should not ideally be look at as ladders. Instead they are messy, winding, unpredictable things…sometimes you take a step sideways and sometimes you step back (I’ve done it) and sometimes you realize the road you were on is not taking you where you want to go. Changing direction Should not be look at in as a failure, think of it as a course correction.

So yes, I am back on the job market. Not because I failed, but because I learned. I learned what matters to me. I learned what environments allow me to do my best work. I learned that staying somewhere that does not fit just to protect pride is far more damaging than admitting a misstep and moving forward with intention for both parties.

If nothing else, this experience reinforced something I wish we normalized much earlier in our careers. You are allowed to be wrong. You are allowed to change your mind. You are allowed to choose yourself. Sometimes the most valuable growth does not come from the wins you post about. It comes from the moments you quietly survive and the clarity that follows.

And if you are standing in that uncomfortable space right now, wondering how you ended up back here, take a breath. This is not the end of your story, it is just a plot twist and sometimes those are the chapters people remember most.

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.