Your Annual Reminder to Take a Break
Entrepreneur Office Hours - Issue #259
Next week is Thanksgiving here in the United States, and that means two things: 1) I won’t be publishing a new issue of EOH; and 2) It’s time for my annual reminder to entrepreneurs everywhere that it’s OK to take a break.
I get it… entrepreneurship is all-consuming. You wake up thinking about your startup. You go to sleep thinking about your startup. And you don’t stop thinking about it anytime in between. And that’s totally fine. But you can still think about it on a beach. Or in the mountains. Or on your couch over a Netflix staycation weekend.
My point is, stepping away from your startup isn't a sign of weakness or lack of commitment — it's actually a strategic move for long-term success. Taking breaks enables renewal. When you allow yourself to unplug, even if just for a day or two, you give your mind the space it needs to recharge and come back with fresh perspectives.
Think about it: some of your best ideas probably didn't come to you while staring at a screen for the tenth hour straight. They likely appeared when you were on a walk, enjoying dinner with friends, or maybe even while binge-watching your favorite show. That's no coincidence. Our brains need downtime to process information and foster creativity.
So this Thanksgiving, and as we move into the holiday season more broadly, remember to give yourself permission to truly disconnect. Enjoy the company of loved ones, indulge in that extra slice of pie, and resist the urge to check your email under the dinner table. Your startup will still be there when you get back, and you'll return with renewed energy and maybe even a brilliant idea or two.
Remember, entrepreneurship is a marathon, not a sprint. Sustainable success comes from pacing yourself, and that includes knowing when to rest. So take this as your official reminder: it's not just okay to take a break—it's essential. Trust me, as someone who burnt himself out multiple times because he didn’t know when to put down the computer, both you and your startup will be better off when you learn to step away.
Podcast: ThoughtWave Episode #5
The Psychology of Free, Building Viral Stories, and What Krispy Kreme Can Teach Entrepreneurs
In this episode of ThoughtWave, Dr. Aaron Dinin and Chris Leithe unravel the power and paradox of “free” in business strategy. They dive into why consumers flock to free donuts, how freemium models can fuel audience building, and why the true value of “free” is more than just giving things away—it’s about storytelling, trust-building, and creating memorable experiences.
From Krispy Kreme giveaways to unconventional classroom experiments involving donut chapels, the duo dissects what makes free offerings effective and how businesses can strategically deploy them to drive growth. They also share actionable insights on leveraging free content, lead magnets, and even discounts to generate trust, build audiences, and craft viral stories.
Listen now on: Apple | Spotify | Online
This week’s new articles…
The Best Entrepreneurs Know When to Take “No” for an Answer
Despite what you’ve always heard, the word “no” isn’t always something entrepreneurs should ignore.
Maybe It’s Time to Stop Believing the Biggest Lie About Entrepreneurs
People’s misconceptions about entrepreneurs create problems inside and outside the startup world.
Office Hours Q&A
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QUESTION:
Hi Aaron,
I've been working on my startup for a while now, and lately I've been struggling with imposter syndrome. I saw it was something you also recently talked about in an Instagram video.
For me, sometimes I feel like I'm not qualified enough to be leading my venture, and it's starting to affect my confidence and decision-making. Have you ever dealt with imposter syndrome in your entrepreneurial journey? If so, how did you overcome it? Any advice for someone in my shoes would be greatly appreciated.
Thanks so much,
Pat
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Let me start by assuring you you're definitely not alone. Imposter syndrome is something just about every entrepreneur grapples with at some point, myself very much included.
I remember early in my entrepreneurial journey, I'd often find myself in rooms full of seasoned business veterans, and I'd think, "Any minute now, they're going to realize I have no idea what I'm doing." The funny thing is, the more entrepreneurs I talked to, the more I realized they were thinking the exact same thing. Even the ones who seemed to have it all figured out were struggling with their own doubts.
With all that in mind, here's what I've learned about dealing with imposter syndrome:
Acknowledge It but Don't Let It Control You: Feeling like you're out of your depth is OK. It’s often a sign you're pushing yourself and growing. The key is not to let those feelings paralyze you. Recognize them, but don't give them the power to dictate your decisions.
Focus on Your Progress: Take a moment to reflect on how far you've come. Every step forward, no matter how small, should be evidence for yourself that you're capable of achieving great things and making good progress toward your goals. So celebrate the wins — they're the things that’ll ultimately give you more confidence.
Remember Everyone Is Figuring It Out: Seriously, everyone. Entrepreneurship doesn't come with an instruction manual. We're all making the best decisions we can with the information we have. The fact you're aware of what you don't know is actually a strength — it means you're open to learning, and that’s an enormous asset in the entrepreneurial world.
Shift Your Perspective on Failure: Instead of seeing potential failures as proof you're not good enough, view them as opportunities to learn and improve. Every entrepreneur faces setbacks; how you respond to them is what actually matters.
Seek Support: Talk to other entrepreneurs, mentors, or anyone you trust. Sharing your feelings can be incredibly freeing, and you'll likely find that others have felt the same way. Sometimes just knowing you're not alone makes a huge difference.
And trust me… you’re definitely not alone.
Got startup questions of your own? Reply to this email with whatever you want to know, and I’ll do my best to answer!