22 Entrepreneurs Reveal Their Worst Habit

UPDATED: May 22, 2023
PUBLISHED: July 20, 2017
22 Entrepreneurs Reveal Their Worst Habit

Everyone has bad habits. Even those who’ve risen to entrepreneurial greatness.

Related: 7 Breakthrough Steps to Shed Negative Habits

Steve Jobs had poor hygiene, Walt Disney smoked three packs a day and Michael Bloomberg has a sodium addiction. But more iconic than their flaws is the success that ensued despite their insufficiencies. What could have been their undoing was, instead, their humanizing characteristic.

And that’s the case with our flaws.

The worst thing any of us can do is hide our imperfections. No matter how glaring, strange or destructive, our shortcomings flourish in the dark, but atrophy in the light.

So in the spirit of transparency, here are 22 entrepreneurs owing up to their worst habit.

1. I do too much at once.

“I continually try to do too much at once. Before, I would take on any idea or project that I liked. Now, I focus more. I still get caught up in doing too many things, but I catch myself before I go too far down that route. It’s my biggest weakness.”

Neil Patel, founder of Neil Patel

2. I start my day with email.

“Checking my email first thing in the morning. It puts me in a responsive start, and focused on everyone’s to-do list except my own.”

—Brian D. Evans, founder of Influencive

3. I’m not always present.

“Not being present. As a hustler—constantly finding possibilities and taking action—I move fast and get things done. But strengths, when overused, can become weaknesses, and too often this causes me to miss the present moment and the people right in front of me, including prioritizing my own health.”

—Carla Taylor, founder and chief happiness officer of Ideavize

4. I power through work.

“Marathoning through the work day. I’ve read the research and know how important it is to get outside, take a break and then come back to work, but I have this mighty urge to power through, especially when the weather is gloomy. Also, gigantic cups of coffee at 4 p.m.”

—Michaela Alexis, president of Grade A Digital

5. I procrastinate.

“In a word: procrastination. I’ll just do that tomorrow is the bane of my professional existence. Likewise, so is social media. It’s so easy to tell myself, This is work. This is personal branding. This is promotion. Really, it’s just nonsense that doesn’t get me any closer to nailing down the stuff that matters.”

—Aaron Orendorff, founder of iconiContent

6. I work when I don’t need to.

“Working when I don’t need to. This sometimes makes it so that I’m working hours that aren’t productive. I think many of us assume that the number of hours we work is equivalent to our production, but this is not true. In fact, I would say the less we work, the more we get done.

—Scott Oldford, founder of INFINITUS

7. I get distracted with metrics.

“Despite over a decade of research to the contrary, I still cannot help but distract myself with vanity metrics here and there. I waste way too much time checking daily downloads of my podcast when that number is completely irrelevant to the long-term success of the show.”

—Jordan Harbinger, host of The Jordan Harbinger Show

8. I get lost in email.

“The first thing I do every morning when I wake up is check my email. I could get lost in it for 15 to 20 minutes before I do things that are super important for the business.”

—Nathan Chan, CEO of Foundr Magazine

9. I’m addicted to TV.

My addiction to TV. Once I end work and finish all of my responsibilities, I lie in bed and watch TV. It’s the best way for me to shut down my brain and to stop thinking about work. But sometimes it gets deadly. Like when I start the first episode to a new TV series. Then I might end up wasting a whole weekend glued in front of the show as opposed to going out into society and conversing with my friends and associates.”

—Leonard Kim, managing partner of Influencetree

10. I isolate myself.

“Not paying attention to the people around me. Most of the time I like to be alone and isolate myself in my room or somewhere far away from everyone else so I can work. It’s almost as if I’m obsessed, which is good and bad. But when it hurts people, it’s bad.”

—Ulyses Osuna, founder of Influencer Press

11. I say yes too much.

I say yes to too many things. I love ideas, and I love vision, and I get excited about strategy. It’s really easy for me to get excited and say yes to anything that seems cool to me. Also, I really love to serve people, and sometimes subconsciously you feel it if you don’t say yes to certain things, you’re not serving that person well.”

—Trevor Mauch, CEO of Carrot

12. I choose busywork.

“Procrastinating bigger projects for the smaller, easier tasks. For example, if I have writing to do, I’ll try to complete all of my other tasks before tackling the writing project.”

—Benji Hyam, co-founder of Grow and Convert

13. I wake up to my phone.

“I check my phone the second my eyes open in the morning. It’s a terrible habit I’ve been trying to crack, but I have clients in Australia and Israel that have likely been emailing me while I was sleeping and I want to see if there’s anything urgent. It’s still not the best way to wake up, though.”

—William Harris, CEO of Elumynt

14. I get sidetracked.

“Getting sidetracked by checking our KPI’s all day long. Like every 15 minutes. It’s almost a subconscious twitch.”

—Matthew Spurr, COO and co-founder of Quuu

15. I second-guess things.  

“Second-guessing. Being an entrepreneur requires you to make 100 decisions each day (or was it 150?). And constantly going backwards to re-analyze previous decisions only wastes time and increases mental anxiety that blocks you from focusing on what matters: bringing in the next client or launching the next campaign.”

—Brad Smith, founder of Codeless

16. I’m addicted to gaming.

Gaming. I’m a gaming addict, and in a world of high-stake deadlines, when push comes to shove, it’s my sleep and fitness schedules that get eaten into for that extra three hours of Witcher 3 or League of Legends. It’s not sustainable, but I have yet to kick it.”

—Jacob McMillen, copywriter and content strategist at JacobMcMillen

17. I multitask.

“The worst habit I have developed over the years is doing multiple things at the same time. It doesn’t only kill productivity, but creates chaos, slows down the process, produces mediocre results and eventually leads to burnout.”

—Tomas Laurinavicius, lifestyle entrepreneur and blogger at Tomas Laurinavicius

18. I get distracted by emails.

“Definitely email. Every time I get an email, I completely forget what I was doing or working on and immediately get distracted. Rather than setting a dedicated time to answer emails each day, I lose focus and jump from one thing to the next.”

—Talia Wolf, founder and chief optimizer at Getuplift

19. I am never satisfied.

My bad habit is being so passionate about reaching a project’s full potential that I keep on optimizing. I am learning to be satisfied with 95 percent instead of 150 percent.”

Johannes Ceh, value enhancer at Strength and Balance

20. I forget to be grateful.

“Not recording all of the beautiful things about life in a gratitude journal. It’s easy for me to get so caught up in everything happening that I lose track of the good in life, and ultimately, my emotional well-being. But if I record all of the wonderful things, I quickly realize I have no reason to complain.”

—Jeremy Miller, chief marketing officer of JR Miller Group

21. I work while I watch TV.

“Working and watching TV. During the NFL Season, I have a bad habit of working in front of the TV while the games are on. We’ve all heard of fake news. This is what I call fake work. I’m not actually working, though I have my laptop in front of me. It’s a pointless activity.”

—Ross Simmonds, founder of GetCrate and Hustle & Grind

22. I always have Gmail open.

“Many productivity sites tell you not to check email first thing in the morning. The thought is by checking your email, you allow other people’s priorities to come before your own. Maybe it’s because I have connections all over the world, but personally, I can’t help myself from opening a Gmail tab.”

—Jason Quey, founder of The Storyteller Marketing

From the ambitious to the wealthy, bad habits abound. Surprisingly, the answer isn’t quitting, but admitting. Because if others can’t relate to you, then you can’t motivate, lead or inspire them. Ironically, freedom is born from sharing your worst, not from hiding it.

In the dark, your worst flourishes. But in the light, it transforms from a deficit into a benefit. People follow and connect when you show them you, and all of your accompanying dysfunction. Only then can you create a better business and brighter future that’s more satisfyingly imperfect than any of us could have expected.

Related: 13 Daily Habits of Highly Successful People

Mike Blankenship has been a freelance writer for 7 years and worked with brands like ClickFunnels, Jeff Bullas, Neil Patel, and more. He's also the co-founder of The Tonic and Tools 4 REI.