I got that question a lot as a kid, and I never had a very good answer. If you feel the same way, I want you to know that’s totally OK. I’m still figuring it out, and I’m 53. I’m in the process of writing a new chapter in my life and career and I thought I’d take a few moments to jot down some of my own thoughts. I don’t know exactly when it happened for me, but there was a moment in my own life where I decided that I could change my own rules or expectations when they no longer served me. It’s a difficult concept to get used to doing if you haven’t done it before, but I’ve found that intentions and decisions are like muscles; the more you exercise them, the stronger they get.
I’ve been stuck in my life and in my career a lot. How do you get unstuck when no one gives you a guidebook? I’ve been incredibly conflicted at times, and that internal conflict for me has felt overwhelming and terrifying at times. I imagine you might feel the same. How can we help each other?
When you were a kid, what did you do on your own that you could get lost in? For me, I’ve always loved solving puzzles and learning about topics that fascinate me. There’s a lot more self-motivation there, and it’s much more likely to last long-term. Ebbs and flows are natural and progress isn’t linear. If you find yourself swimming against the tide and it becomes too much to bear, it’s probably an indicator that you should be looking for guidance from people who have your best interests in mind and who also can support or guide you.
What matters most to you and why? What do you value? In my case, these answers have changed over time; then again, I’ve been working for almost 40 years. I’ve done everything from bussing tables to landscaping to working retail. I’ve also done stints in discount brokerage, warehouse management, and software design & consulting. I’ve gleaned something from every opportunity, and much of the nuanced understanding I’ve had has been a direct result of some of the early dues I paid. No matter what you do, you’ll learn something from every opportunity, so might as well embrace the suck.
What price are you willing to pay for what you want? I’ve given more than anyone probably should, if I’m being completely honest. I’ve also found incredible fulfillment and joy by and focusing on the work, focusing on mastery, and focusing on the things within my control. Getting clear on the sacrifices you’re willing to make and where you’re not willing to bend is critical.
What comes naturally to you? What gifts do you have that are unique to you? The older I get, the more I’m a firm believer that skills of just about any kind can be developed, just like muscles. I’ve been dabbling in tons of different areas for my whole life, and I find it incredibly fulfilling to learn about all kinds of topics. Small talk has always been a struggle for me; finding people to nerd out with is fun and a great way to connect with people, accelerate learning and have more fun.
What am I missing? Let me know what you think!

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