Lessons from the Trenches: Career Branding Good, Bad, and Ugly (SB1674)

The Stacking Benjamins Show

Joe Saul-Sehy and Josh ‘OG’ Bannerman, CFP

Personal Finance, Financial Planning, Education, Retirement, Investing, Cfp, Business, Money

4.4 • 2K Ratings

🗓️ 25 April 2025

⏱️ 61 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

What do zipper injuries, holiday party mishaps, and servant leadership have in common? They’re all part of today’s wide-ranging look at careers—what to do, what not to do, and how to make your next move smarter (and safer).

Joe Saul-Sehy, OG, and Neighbor Doug are joined by contributors Sandy Smith, Jesse Cramer, and a few classic career stories from the SB vault. Together, they explore:

The surprising power of likability in the workplace
How consistency and personal branding can open big doors
Why some leadership styles flop and others inspire
The real-life career missteps that made us all a little wiser
A closer look at the Elevate Conference, which champions financial literacy for Black women

And of course, it wouldn’t be a basement episode without a trivia challenge. This time, Doug delivers a stat that’ll make every listener squirm—let’s just say it involves zippers and emergency rooms.

Whether you're climbing the corporate ladder, considering a leap, or just trying to avoid HR’s bad side, this episode packs in real advice and memorable stories from people who’ve been there, done that, and got the awkward email to prove it.

Smart moves, cautionary tales, and Doug’s very specific warning about pants—this one's got it all.

FULL SHOW NOTES: https://www.stackingbenjamins.com/improve-your-career-trajectory-1674/

Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201

Enjoy!

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Transcript

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0:00.0	Describe your perfect date.
0:04.0	I'd have to say April 25th,
0:07.0	because it's not too hot, not too cold.
0:10.0	All you need is a light jacket.
0:17.0	Live from the basement of the YouTube headquarters, it's the Stacking Benjamin Show.
0:23.6	I'm Joe's Mom's Neighbor, Doug, and this week we've been helping you improve your career trajectory.
0:38.8	And today, well, we'll polish it off with three people who've successfully navigated careers of their own.
0:45.0	We'll talk missteps, unforced errors, and strategic genius in the office.
0:50.5	But that's not all.
0:51.8	We'll pause briefly halfway through for today's edition of our
0:55.9	year-long trivia challenge. And now, a guy who might have just hit the pause button on an
1:01.8	Xbox just to come join us. It's Joe Saul-CI.
1:08.9	Oh, no, no, no, no, no, not in the middle of a workday, although I haven't played in this cool new game. Doug called South of Midnight. I don't know if you've seen that game. I have not, but I'm sure you'll suck me into that. Some fantastic goodness. Hey, everybody, welcome to the Work Hard, Play hard podcast. I am Joe Saul Seehigh, and we've got a fantastic way to end
1:28.3	career branding week. We're going to share some salaciousness, some amazing things people have done
1:34.7	to blow up their career that you may be able to learn from. And then sometimes some people
1:40.3	might have made their career. We've got the perfect people for that. We'll introduce our guest of honored last. But let's start off with a guy across the card table from me, who's had a whole career in financial planning. Mr. O.G's here. How are you, man? It's like I've had two careers in financial planning. It's been so long. Well, you and I, way back in the day in our American Express days, we saw some stuff.
2:02.1	We saw some people blow up some careers pretty, pretty well.
2:06.1	You know, I don't have any, I don't have any memories of any of that stuff, honestly.
2:11.2	You blocked it all out?
2:12.4	Yeah, I mean, totally have.
2:14.1	And when I was thinking about this, I was thinking more kind of broad brushstroke of
2:18.2	ways to do it, not any particular stories. So I'll be interested to hear you tell me the things
	...

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