Over the last 10–20 years I have felt this "itch." It comes and goes, but it always comes back. It presents itself at different times, but the underlying trend is the same. When things get exhausting, unfulfilling, or mundane, I want to leave and experience something new.
We have all said or heard someone say the words, "I want to open a coffee shop" or "I want to move to the country." These words are usually uttered when someone is at a point in their life when everything feels like too much or too little. They are either working their asses off or not doing enough to feel fulfilled.
For me, I got to this point when I was unappreciated in a retail job. It also happened when I was overworked in a SaaS role. In my personal life, it happened when the people in my life were not making me feel good about myself and the locale was not worth keeping me there.
This manifested with me switching jobs and even pivoting careers entirely. This has even meant moving across the country. While you might be thinking this only happens to people when they are at their worst, I can guarantee you that is not true. Even when people are seemingly in the perfect place, doing the perfect thing, surrounded by the perfect people, they have this itch.
For the last 4.5 years, I have lived exactly where I want to be, working for myself, making decent money. I always get questions about what I do and where I live, and people reply, "well that's nice." While it is, guess what? The itch is back.
It came back about two years ago. My wife and I traveled full time for 5 months, trying to find a new place to call home. Not because we don't love Portland — we do. We felt like there was something missing. So we searched. The search came back empty, and we moved back to Portland for the last year.
In the last year, we rented a very nice place in a quiet neighborhood and set down more roots than we should have. While we still live a modular life, we acquired a few not-so-modular things. This has been the salve to our itch; it's been nice. But there was still something missing. The only thing we can think of is the lack of meaningful connections in our life. We all know that it is hard to meet people as an adult in 2025. Thinking I might be able to find connections through work, I decided to start looking for hybrid jobs.
While I have loved working for myself, I noticed that I do not love having to do all the things. Mostly, I hate marketing. I dislike SEO and keywords, outbound marketing makes me feel gross, and I loathe social media. So this has meant an inconsistent pipeline. Don't get me wrong, I have done well for myself, considering I do that marketing while hating it.
So after 150+ job applications and a handful of interviews, I have accepted a role at a great company. I plan on revealing it, but I'll wait a few weeks to move, settle in, and then let you all know the details. Oh yeah, we are moving. Portland has treated us well, but there is not much opportunity here, so I cast a wider net and that net landed in San Francisco.
There is a trend when we move, I am not sure why, but I can only sum it up with one word — frantically. Nearly every time we have to move, either by choice or circumstance, it is in a mad dash. I was officially offered the role last Monday and will be moving out of my apartment next Friday. Two weeks, that's pretty frantic for a move across states.
This itch has been so deep for so long, I don't know if this move, career change, and hybrid work culture will scratch it or not. I think I will have to layer on some additional changes. But first, the move and new job.
I have known a lot of people in my life who have told me about their versions of this itch. They have bared their hearts to me, telling me how they need change, but so few of them act on it. I don't know if my acting on it is best or counterproductive, but I know that it is not in my nature not to try. Hopefully, I can report back in 6–12 months, letting you know that we have found our place, careers, and people. If not, I'll be giving you another frantic update.