It’s coming up on 10 years since I started working in tech. Maybe closer to 15 if we count the years of web development work that mostly involved moving content between CMS platforms at my univerity, doing computer repair for my schools and local businesses while I was in high school. But 2013 is when I got my first job at a big tech company, and probably changed my life in ways I had never expected. Many things have changed in the last 10 years, getting jobs I really wanted and then moving on from those very same jobs for something different.

I recently turned 30. I thought I’d have it all figured out. If you ask most people in my life, they’ll probably tell you that I do have it all figured out. That I have my life together. I have a wonderful girlfriend, a job that pays me more than anyone really deserves and challenges me in ways I enjoy nearly every day. I have a car I love driving, I paid off my student loans years ago, I have a nice apartment with a nice TV, a nice bed, a nice home office, etc. By all accounts, I am doing far better than even I expected when I started this journey.

Along the way, I even picked up several extracurricular pursuits so that I could explore other things I liked. I have tens of thousands of plays on soundcloud, with songs on spotify to boot. I was given the opportunity to publish videos with Hak5, who I watched a ton while starting my journey into tech. (Sorry I wasn’t more consistent with that, Darren!) I’ve spoken at conferences about things I cared about. I’ve built software that several tech giants use regularly. I’ve won CTFs and I’ve lost many more. I’ve built CTFs and mentored students as they began their own journeys.

But there, just beneath the surface, I’ve faced the same struggles for as long as I’ve felt like I had any control over my life. And perhaps that is an important distinction, because there were times as a teenager where I didn’t think I’d make it through high school. Times where I thought I’d not make it through the night, even. But I also seemed to thrive in adversity, and as things got harder, I got more focused. I got into college, got involved in the computer community at my school, got my degree, got a job. Even with as much as I’d like to take credit for my success, I have to admit that mostly I was lucky.

Once I started working full time, I lost basically all structure and adversity that drove me through school. I didn’t know what to do with myself anymore. In high school, my goal posts were to graduate high school. In my senior year, my goal posts were to get into a college. Once I got in, my goal posts were to find a job so I could afford to stay in school. Once I got that job, my goal posts were to finish school and get a full time job in tech. I knew I was interested in security, but I had no experience in it. I got lucky with the job I did get, thanks to a Principal Engineer at Intel seeing something in me that I didn’t.

Once I was working full time, I started getting more interested in security as profession, and started to move my goal posts to working full time in security. There was only one problem. Everything I learned about security up until now was about how to break websites. I had no idea what a “Threat Intelligence Analyst” did, or literally any other word soup that corporate companies had to describe different security roles. I learned about red teaming from the red team lead at Intel and began volunteering to work with them in addition to my normal job. New goal post: get hired on a red team. And so I did, about a year later.

This is when it really started to get confusing for me. I had a job I really enjoyed, even when I hated certain parts of it. I had to start finding new goals, and it seemed like the goals had to start to become more tightly scoped. No longer were my goals about huge life changing events. My goals were things like “Lead an engagement at work,” “build a useful tool for the team,” etc. Intel didn’t really pay me competitively, I learned from other red teamers, so I ended up with a short term big goal again – get paid competitively.

I switched to another red team job and nearly doubled my salary (and more than doubled my total compensation). I ran out of goal posts again. I made good money, I had a team I enjoyed working with. I basically bumbled through the next couple years not really knowing where I was going, just taking things as they came. Eventually I got frustrated, feeling like my work wasn’t being recognized by the organization, and my compensation wasn’t being adjusted either. I ended up leaving red team work, despite having an offer to join another red team, in order to take a job that would stretch my skills further and force me to level up in things I wasn’t familiar with.

That was a great decision, and I’m happy in my job now. I’m a staff security engineer, and I work very closely with our software engineers to build great things. I work closely with our IT to secure our workstations and corporate assets. I work with compliance and risk to align on frameworks and audit requirements. I understand our infrastructure like the back of my hand. I’m happy, and I’m damn good at what I do.

But now… where are my goal posts? I feel lost without them. Where do I go from here? Titles are made up. Compensation bumps, while appreciated, stopped making a significant difference in my life years ago.

I feel almost obsessed. Compelled to need some goal in order to have meaning in my life. And that’s stupid. I should be happy with what I have. But I can’t help but constantly be wondering what is next.

I want to build a startup. But startup culture is dumb and I don’t really want to build another mediocre web service that addresses a minor inconvenience that other startups experience. Instead of a startup, I want to build something open source. I want to democratize and decentralize the solution to a problem that people experience. But then how do I survive, if I’m not getting paid? Instead of building something, I’ll teach what I know through a series of videos and blogs. I’ll make it free so that the people who were like me, who couldn’t afford to spend $59.99 on a course, will be able to benefit and change their lives. But I still need to make a living. I’ll run ads to support my free content. But ads are privacy invasive, tracking users across the web and building profiles on people. I don’t agree with that, so I guess I can find brand sponsorship deals. This stream of thought brought to you by ExpressVPN. But I feel slimy at the thought of running a sponsorship deal for something I don’t use myself. I haven’t even made anything yet, why am I worried about sponsorship deals?

I want to make a difference in my community. I don’t need to make a big splash in the world, but I do feel like I need to make a difference for those around me. The capitalistic drive to monetize everything in tech, I guess in the world, but in tech in particular for me, makes me feel gross. We’re monetizing education. We’re monetizing communication. We’re monetizing attention.

I can’t find my goal posts anymore, and it’s driving me crazy.