How Do You Stay Ambitious When Work Stops Feeling Stable?

I recently spent the last few weeks completely redesigning my personal website (https://tyrellcromoshuk.com/) from the ground up in Codex, which I think looks pretty damn good if I say so myself. The reason? I’m back on the job market and need to make sure I can stand out from the crowd.

I’ve honestly written about unemployment far more than I ever expected to when I started this blog back in 2014. At this point, there is an entire section of the website dedicated to work, ambition, and unemployment, which I’m hoping is both useful for readers and slightly depressing for me to think about… hah. Every time I have found a new role, I have hoped I could close that chapter and write about literally anything else.

Yet here we are again.

Although leaving my most recent gig has made me think about something slightly different this time: how do you stay ambitious when work no longer feels stable? I have already written about the fear, embarrassment, and money anxiety of losing my job and the broader complexities of unemployment. I have written about becoming your work and needing to build an identity outside of whatever happens to appear in your LinkedIn headline. Apparently, writing those lessons down does not mean you automatically master them because I am still working through a lot of the same feelings years later (which I know I’ve said in previous blogs, but just reminding you that we’re all a work in progress).

For most of my career, ambition has meant moving upward and forward: a better title, more responsibility, a bigger team, higher compensation, and overall, the chance to work on increasingly interesting and difficult problems. I’ve always believed that if I performed well and continued to prove myself, each step of my career would create more security than the one before it. I wasn’t so ignorant as to think that there wouldn’t be stress or risk, but I did think that I’d eventually reach a level where I had enough experience and value to bring to the table that I would stop having to worry about it all collapsing. As I wrote about in the previous blog, I no longer think that level of security exists in the world.

Listen, your performance still matters, but I don’t think that it can protect you from every decision that’s out of your control. Your role can disappear for many reasons that have nothing to do with how well you do your job. It doesn’t really matter nowadays whether you did everything you were asked, because there’s still a decent chance you’ll find yourself staring at an empty calendar a week later and wondering to yourself what you are supposed to fill your day with. For me, I had this underlying thought that the better paying jobs were also more secure, but I have realized in recent times that the higher salary actually makes your ‘fall’ feel worse because your life slowly expands around the higher income. You take on larger bills, have more discretionary income, make plans based on said income, and eventually forget how quickly the money can stop coming in. I’ve personally been fortunate enough to build savings and investments that give me a bit of breathing room, but that does not remove my anxiety about the future and how I’ll fund my life. The security blanket just means that panic doesn’t have to influence every decision immediately.

In today’s world, multiple layoffs are becoming the norm, and that makes it tempting to stop caring when you do find a gig. Why give a company your best ideas, take on their difficult problems, and become emotionally invested when the relationship can end without your permission? I’ve talked to a few peers who think the smarter approach is to do the bare minimum, collect the money, and keep enough emotional distance that losing the job won’t hurt them. My problem? I actually like the work I do and want to make sure it’s better than just enough.

I like solving growth problems, building things, leading teams, and seeing whether an idea can turn into a real result. There’s a feeling I get from seeing the work I’ve done actually impact customers' lives that I can’t fully describe in words. On top of that, I like feeling useful and continually getting better at something. I don’t know that I have the capacity to pretend that I no longer care about my career, and I don’t feel like it would make me better either; if anything, it would just be something else that my career instability has taken away from me.

I don’t think the answer is becoming less ambitious, but I do think there’s something that a lot of us need to change when it comes to approaching our careers. I think we need to stop allowing ambition to depend entirely on one employer.

A few years ago, I wrote that I needed to become more than my work. I still agree with that, but I now think there is a second part to the lesson I didn’t realize back then. I also need my work to become more than one job. My career should include the skills I have built, the people I have helped, the relationships I have maintained, the writing I have published, the businesses I have advised, and the projects I create without anyone assigning them to me. It shouldn’t and doesn’t need to be focused on the most recent role, despite recruiters and LinkedIn telling you it should.

That is part of why I have been rebuilding this blog and my personal website. It is why I have taken on consulting work, explored new ideas, and started building tools that solve problems I am interested in. I don’t expect every project to become a successful company or meaningful source of income. Honestly, some of them may go nowhere. The value is that they remind me I can create momentum outside someone else’s organization. As much as I hate the term “vibe coding”, it’s pretty cool what you can build with AI nowadays, and I’ve been throwing myself headfirst into it. I also want to be careful not to turn this into another version of hustle culture where every hobby needs to become a side business. Optionality does not mean working every waking hour because you are terrified of being laid off. Sometimes it means maintaining relationships before you need help, learning as your industry changes, keeping a portfolio, saving enough to avoid taking the first terrible job offered to you, and preserving parts of your life that have nothing to do with professional success. That last part is probably the most important for me at this point.

I have always attached a lot of my self-worth to achievement. A large title made me feel successful. A recognizable company made me feel validated. A difficult job gave structure to my days and a simple answer when somebody asked what I did. When the job disappeared, so did a large portion of how I understood myself. I’m still actively trying to change that part of me. Yes, I am a marketer, but I am also a writer, partner, friend, traveller, collector, gamer, and person with an annoying number of thoughts running through my head at any given time. Those parts of me do not disappear because a company removes my email access. I need to continue investing in them when work is going well, rather than desperately trying to rediscover them every time my career pauses.

None of this means I have stopped wanting the big opportunity. I still want to lead important work, earn well, build successful businesses, and prove that I am capable of more. I still get jealous when I see somebody announce a role I would have loved. I still have days where I question whether my career has peaked or whether repeated layoffs say something about me that I do not want to admit. The difference is that I am trying to build a version of ambition that one company cannot completely take away.

So my advice after navigating a roller coaster of a career? Care about your career. Become excellent at something (or multiple things). Pursue the title, negotiate the salary, and be proud when your work creates meaningful results. Just try not to hand one employer your income, identity, confidence, community, and entire future at the same time.