I think it's easy to look upwards and think that life gets easier as you progress. Whatever "progress" that might be. Further along with a career, married, good friends, nice car, nice white picket fence, etc.
"If only I get to this point, I'll be happier," "If only I get that promotion and start making money, everything will be easier." -- I guess some of the time these statements are true. But quite often they are not. Largely, life is about picking your poison.
You can trade finacial difficulties for higher job stress, or stresses of loneliness with stresses of being in a relationship. A lot of people also look at any degree of success greater than their own, and imagine these people to be happy, rarely ever feeling down, etc.
The position I'm in now is pretty great. I can work from anywhere in the country, travel as much as I want, pick my hours, and generally speaking finances are just not a problem for me. If I want something I can get it. I'm not saying I can snap my fingers and land a $500,000 house on forty acres in the mountains, but finances are just no longer a real concern. And yes, that is a huge stress relief. So beyond my mostly worry-free financial situation, I have absolutely wonderful friends and family. My parents are extraordinarily loving and supportive. They don't fight, their 30th wedding anniversary just came up. And my friends are the sort of people who will tell me when I'm wrong and some would even fly across the country to help me if I really needed it. To say that I'm blessed is an understatement.
Now with these things said and while I am glossing over rather important details about the stress of running a company, I still have tons of low moments. I can literally get out and do most whatever I want, yet many days I just feel depressed focusing on even bigger problems (that I may never be able to solve), or feeling down about society in the ways I've been betrayed. A couple years ago I wrote some software called "days to live", basically a way of tracking finances where I factored in daily expenses vs money in the bank to determine how many days I could feed/shelter myself. I was writing a book, working as a mobile mechanic, applied for Postmates, writing the initial components to SporeStack, and even painted to try and make ends meet. I also had a thousand dollars stolen from my desk, which was most of the savings I had left.
And yes, this was all quite stressful. And some things hadn't happened then that get me down now. But all in all, I don't think I'm any happier now than I was then. In fact, in some ways I was definitely happier then. I'd say my job stress was actually less then than it is now, even on a day that I don't do anything.
I think it's ridiculous how uninspired I can be now, even when I'm working on exactly what I want to be working on. Part of me gets excited and somehow feels fulfilled over a silly "server count" metric I have in Datadog. When the number goes up and hits a new milestone, I feel good. When it goes down, I feel sad.
My takeaway is that life is always going to be a struggle. For me, a lot of that has been finding new ways to stress myself as I relieve one burden or another. Also, you can always make the best or the worst of what you have now, and the best and worst of any life situation is usually pretty far apart. With a good attitude someone making minimum wage can be happier than a movie star on the beach after two months of filming, taking off two weeks just to relax.
I am definitely more successful now than I was a couple years ago. And I don't regret that, even if my happiness isn't moving up with it. But the success opens the possibilities for me to make even bigger mistakes than before. Or if I do it right, I can leverage it as a tool to keep moving forward.
There's no way around it. Stress is part of struggle and struggle builds character better than anything else. And the stress isn't going away any time soon.