If you could go back and restart your career with what you know now, what would you do differently? Would you choose a different path, take bigger risks earlier, or aim for a different role and industry altogether? Curious where people think they’d be today with that hindsight.

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My careerpath was mostly by happenstance, but it turned out well. I probably would have taken greater risks when I was younger, but I applied the slow and steady wins the race approach. Nearly 38 years later, I am ready to close this chapter and begin anew.

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That’s a great perspective. There’s something to be said for the slow and steady path, especially when it still gets you somewhere you’re proud of. And honestly, taking a new swing after all that time is pretty inspiring.

I love where I’m at and how I got here. But if I could change one thing about career path, I would have gotten into 100% commission sales/business development sooner.

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Keep Jesus as my centered focus versus stressing numbers that I couldn't control and have a more humble attitude. Especially when I was around people that had more experience than me.

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I posted a similar-ish question. Whether or not chasing something bigger was worth it. As someone who has, my 2 cents, find something you enjoy, a group of people you like, a manager who inspires you. Work is a piece of the pie. Focus your energy on the rest of the pie. Because “making it” is nice but not a whole lot without everything else.

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That’s a great perspective. Easy to get caught up in chasing the “bigger” thing and forget how much the day-to-day and people actually matter. The rest of the pie really does count more than we think.

Listen to my mother and be a doctor

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Haha, hard to argue with that, but hey, you’re a director now, which is not bad at all :)

I’m in a fairly good spot right now… but in hindsight, I would have gone after bigger clients earlier in my career… go for home runs instead of singles and doubles…

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That’s really relatable. It’s easy early on to default to what feels safe, especially when we're still figuring things out. But looking back, those bigger swings are usually what move the needle the most, even if they don’t always work out.

I wish I would’ve known how big of an impact the first role I took out of college would have on my career. At the time, I was just happy to get a job, but I didn’t realize how difficult it would be to get a role in another industry

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That's actually very true!

Avoid service roles.

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I would have pursued a job with a generous pension, married someone with a generous pension and never saved a dollar. Those people are smart. Lake houses, boats, vacations. I have a client who’s pension is $20,000 a month.

Honestly, when you put it like that… hard not to think they cracked the code. A $20,000 a month pension is wild.

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Yes I would go into FAANG

I wouldn’t try to be a chef. I would go to college. Business Administration or Liberal Arts degree.

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