This Should Have Been An Email, Episode 10, is for the people who are tired of the polished career advice that sounds good on LinkedIn, but does nothing for you on a random Tuesday when you're frustrated, stuck, or quietly wondering if you're even in the right room anymore.
In this conversation, I sit down with Lindsey Parsons (Associate Director of Sales at Feathr), and we get into the real stuff. What it looks like to chase meaning in your work, how grief can change the way you see your career, and why "being good" at your job is not the same thing as feeling proud of what you do every day.
We talk about the advice her dad gave her that changed how she handles conflict at work, why most people stay in roles 12 to 18 months longer than they should, and how fear shows up as comfort, logic, and "being responsible" when it's really just keeping you small.
We also get into remote work, the loss of the water-cooler learning moments, the slow decline of professionalism, and yes… the story of someone ripping a vape during a sales call (I still can't believe that happened).
And then we go full circle on risk. Not the motivational poster version. The real version. The kind where you have a mortgage, a family, another baby on the way, and you still have to decide if you're going to play it safe forever or take the chance you keep thinking about.
If you're in sales, leadership, tech, nonprofit work, or just a human trying to figure out what the next move should be, you're going to get something from this one.
Be on the lookout for more episodes in 2026!
Timestamps
00:00 Intro and why I'm bringing on more real people
00:38 Meet Lindsey Parsons and Feathr
01:13 Why nonprofits and the career shift after loss
03:05 Best career advice: pause before you react
05:55 Career regrets and staying too long
07:49 Fear, comfort, and the unknown
09:05 Saying yes and what hesitation costs you
11:48 Why adults avoid failure
14:12 Risk when life gets real
17:06 Remote work and networking
18:40 Four-day work week take
20:29 Meetings are out of control
23:14 What she wants next (VP of Sales)
27:19 The vape-on-a-call story
28:40 Coaching vs mentorship
33:00 Learning, AI, and ChatGPT
38:13 Best career advice: take the chance, take the risk
39:00 Wrap up
Follow Lindsey Parsons on LinkedIn.