What are your values? Last night after bible study, I asked a friend, what were your regrets in your 20's? Since we are nearing mid-late 30s, this was a very relevant question plus there were younger people that can learn from our mistakes.
I thought about what I could have done differently, probably be more patient with investing, probably chosen a different major (more related to business/finance), probably been smarter about dating/marriage, probably bought a house sooner, but even as I went through all those choices I could have done... I knew I wouldn't have done them any sooner or different because I just didn't have the foreknowledge.
I did most of those things thinking I was doing the right thing AT THE TIME. How do you plan for something? I learned a lot through the mistakes and I think those mistakes are probably the best teacher I will ever have.
I could have stayed in teaching, but I took a path that paid a lot more. I could have started my graduate school earlier, instead of struggling now with a wife, two kids (a third one coming), house payments, a job, etc. But hindsight is definitely 20/20.
What will I tell the next generation? Probably figure out what your values are. Do you want to have financial security? Do you want to pursue a particular field? Do you want freedom to travel? Do you want a family? Whatever you decide on a macro-level, you can then adjust your life to fit it, whether it is through large scale job change, or small scale volunteering, networking, part-time gigs, whatever. I don't know the secret to anything, I do know that if you don't try, you won't change.
Your career, your life is not a comparison to the world. You will fail and succeed in life, whether you try or not. You will look dumb or stupid compared to some people and you will look like a hotshot compared to others. But you do not live your life comparing yourself to what some other person in their mid to late 30s. No. You compare yourself 5, 10, 15 years ago to your present. You see what you have accomplished, you see what areas you have grown in... but you also see those areas you want to improve and are still weak. Those are the areas you should work on. This requires failing. This requires trying over and over and practicing over and over again. For this is the only way to grow.
If you stick only to the tried and true, you won't grow. The tried and true works for you because you know this system and you will grow complacent in this system. Same with your fitness workouts. You need muscle confusion. Same with your life. You need body confusion, spirit confusion... in order to grow in your life.
Probably my dumbest career move was quit a nice paying engineering gig to spend two years in China. My dad said it was dumb, I couldn't find any work after I got back to the states. I loafed around for another 3-4 years before landing my current job. But in terms of personal growth, it was the most I had grown in a long time. I traveled the world, I spoke another language, I met interesting people, I found out who I was and who I wasn't, started figuring out what I valued and what I don't value.
So. What do you value? Let that be your guide to more intense growth.