Samantha C. Prestidge

Lead Well. Work Simply. Scale Smart. Sometimes the thing that makes us lose our sanity in business isn’t the workload. It’s the comparison. For high performers, resentment doesn’t usually show up in dramatic ways. We don’t actually want to quit the business or burn it all down. (Okay, maybe there are days where I’ve thought, “Forget it, I’ll scrap everything and start over.”) But most of the time, resentment is quieter. It’s that subtle frustration where you start to resent the business… and...

Lead Well. Work Simply. Scale Smart. I used to resent my kids. Not because I didn’t love being their mom, but because I felt like they were holding me back from my business. Networking breakfasts? Off the table because of daycare drop-offs. Evening happy hours? Impossible with dinner, bath time, and bedtime routines that left me too drained to be productive. I’d catch myself envying the business owners who didn’t have those constraints, who seemed free to hustle at all hours. Over time,...

Lead Well. Work Simply. Scale Smart. Last week, I tried to get a window quote. Instead of looking at the windows, the salesperson insisted I sit through a 60–90 minute pitch before we could even look at the windows. When I asked if we could walk through the house and issues first, he flat-out refused. I get the importance of a sales process. But a rigid pitch-first, serve-later approach doesn’t build trust—it builds resistance. That’s why my own sales strategy leans on transparency and...

Lead Well. Work Simply. Scale Smart. “Let me know what you need help with.” “I’m here to support you.” “Call me anytime.” …crickets. Days later, I’m thinking, Why didn’t you call me? Then comes the follow-up conversation: Next time, talk to me before you get to this point. And finally, the part I wish I could tattoo on every team member’s brain: You didn’t have to figure this problem out on your own. These aren’t lines I pulled from a leadership book. They’re things I’ve actually said — more...

Lead Well. Work Simply. Scale Smart. There have been moments in my business where I questioned every single person on my team—why are they even here? There have been moments where I wanted to burn it all down—and I’ll admit, some of my dumb decisions probably sparked fires that didn’t need to be there. But in those moments, when I finally stepped back and took a real look at what was happening, I realized that I was actually the problem in most of the cases. I was the pyromaniac that had to...

Lead Well. Work Simply. Scale Smart. Work isn’t life. I know that goes against what most of us were taught - starting in kindergarten when we were asked to draw what we wanted to be when we grew up. But running your business or leading a team shouldn’t take up 99% of your mental bandwidth (or your physical time). If it does, I hate to break it to you… but something’s off.*cue cringing vulnerability* Last year, I worked 4–5 days a week. Some weeks I was slammed with meetings, projects, events...

Lead Well. Work Simply. Scale Smart. I have a secret... On my CliftonStrengths, Consistency ranks 32 out of 34. *Gasp.* Most people assume I’m a super type-A person...but if I’m being totally honest, I frequently forget my kids’ water bottles on hot days, I secretly love a last-minute productive procrastination sprint, and I definitely don’t always have my sh*t together. What I do try to keep together are systems and structures that let me bounce between “let’s see what happens” free spirit...

Lead Well. Work Simply. Scale Smart. I didn’t think teaching my kid to ride a bike would double as a gut check on how I’ve led teams… but here we are. We skipped the crowded parks and found a giant empty parking lot. Made sure he knew he had to nail balancing before he ever got a big kid bike. Walked him through braking, steering, all the basics. Cheered like crazy every time he stuck with it. Simple, right? Set the right environment, set clear expectations, give clear instructions, celebrate...

Lead Well. Work Simply. Scale Smart. I didn’t exactly plan for my newsletter to become a weekly rundown of my most expensive business mistakes... but hey, here we are. At least you get to learn from them without the bill or the headache. This week’s hard-earned lesson? Skimping on marketing support. I’ve hired execution help when what I really needed was someone to help me think, plan, and get clear. And surprise—it backfired. Because no matter how skilled the VA or contractor, they can’t...

Lead Well. Work Simply. Scale Smart. I’ve wasted way too much time trying to reverse-engineer someone else’s “perfect” system. Sales systems, marketing systems, management systems—I’ve chased all of them at one point or another, hoping that if I just copied the right formula, I’d finally feel like I was doing business the “right” way. Spoiler: I wasn’t. Instead, I’ve bounced between accounting software for no good reason, created an overly complex expense process with a VA, over-engineered...