How to Get Out of a Rut: 19 Entrepreneurs Share Their Secrets

This post is part of Tech Cocktail’s “Psychological Guide to Starting Up,” bringing you insights on the psychological and emotional challenges of startups throughout June.

Entrepreneurship is not for the faint of heart.  The emotional roller coaster will present many highs and lows.  Because managing and motivating your team will require a more consistently positive demeanor, having ways to dig yourself out of these lows is crucial.

That’s why I’ve picked the brain of 19 entrepreneurs, those who’ve directly endured the rigors of starting up, to share their top strategies for reversing a negative thought cycle.

19 Rut Busting Tips For Entrepreneurs, From Entrepreneurs

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1) Practice Gratitude

When ever I feel like I’m stuck in a rut, I do two things. First, I think about all the things about my company that I’m grateful for: my team, the flexibility, the constant learning, the experiences I’ve had (and I have a note on my iPhone that I keep adding to in case I’m having a hard time thinking of things). Second, I ask myself what else I’d rather be doing. Even on my worst day at UniversityParent, there’s not another idea I’d rather be working on. Once I remember that, it’s easy to pull myself out of a rut.

 – Sarah Schupp, CEO & Founder of

2) Pull yourself out

Ups and downs as an entrepreneur are inevitable. Especially downs. Usually you fall into a rut when you’re so deep, mentally, in the day to day grind that your emotions are directly affected by the state of things. A founder has to see their startup from a higher level and realize that the ups and downs are a natural part of the process. Take a walk somewhere and pull your mind out of the day to day stuff. Remind yourself of the bigger picture.

David Spinks, CEO of Feast

3) Find the Joy

Typically, if I’m in a rut it’s because there is a lack of joy in how I’m filling my day. Talking that out with a confidante (our COO is my best friend) or with our company psychologist, with a therapist, and sometimes with my wife, are all ways I remove psychological roadblocks that can otherwise inhibit me for long stretches. The goal is to uncover what shift I could make that would move me back into that dreaming space where I thrive as the head of the company.

– Corey Michael Blake, President of Round Table Companies

4) Accept, disconnect and realign

As entrepreneurs, we don’t accept failure easily and believe in persistence. Sometimes, we have to accept that we need recharging of our batteries – this is the first step to recovering from a rut. Second, we need to take a break and spend time doing things that make us happy – whether that is spending time with friends and family, music or arts, or gardening. We need to also ask why we do what we do and realign with the grater purpose to find new fuel to keep going.

 – Shradha Agarwal, Co-Founder/Chief Strategy Officer of ContextMedia

5) Leverage Lyrical Lifts When You are Mentally Down

I started collecting hip hop lyrics that moved me.  It worked so well I created a site with over 200 Hip Hop Affirmations & a book.  I can hit random on the Tumblr site and get a dose of Diddy or Jay-Z matched with an original affirmation.

Mike Bruny, Founder and Chief Ambassador of

6) Changing up my Workspace

Whenever I’m in a rut, I change my work environment. I switch from my desktop computer to my laptop, and sometimes I take it to the park so I can get out of the house. I find the change to be refreshing and it usually gets me back on track.

 – Andrew Schrage, Co-Owner of Money Crashers Personal Finance

7) Kick things hard

I’ve been training at Krav Maga for 6 years and now a Green Belt (level 4). I must go three times a week to reset myself and since it’s team work, if I don’t focus on the class, I’ll get a black eye. It’s amazing for pressing the default button and helps me to stop thinking about work for a couple of hours. That’s key – not thinking!

– Heddi Cundle, Big Cheese of

8) Focus on Past Victories

Push through your psychological rut with increased self confidence by remembering victories of the past.  Whether it was hitting revenue milestones, user acquisition goals, or even a successful marriage or partnership, leverage those wins to boost your psyche and that will help you battle the challenges of today.

– Anthony Saladino, Co-Founder and CEO of Kitchen Cabinet Kings

9) “Any pessimist I ain’t talk to them, plus I ain’t got a phone in my apartment” – Kanye West

Within the last year I was in a rut myself and thought I wouldn’t be able to get out of it, which caused a negative impact on both my personal and business life. Then one day I had enough. I packed 1 suitcase, moved to a new city, got rid of every person in my life who was bringing me down, and woke up the next day a new man. The day I started surrounding myself with people who brought positivity, motivation, and new points of view was the day that I dug myself out of my rut and took on this world head strong. Now all I say to negativity is “any pessimist I ain’t talk to them, plus I ain’t got a phone in my apartment.

– Shahzil (Shaz) Amin, CEO of Blue Track Media

10) The Glass is Always Half Full

As an entrepreneur, you’re likely to have more lows than you do highs on the road of life. Most successful entrepreneurs fail time and time again before finally breaking through – and they only stay on track by keeping a positive mindset. Just as negative thoughts and words lead to negative outcomes, so do optimistic, action-oriented behaviors lead to success. Think happy thoughts, and happy outcomes will follow.

– Brendan Mangus, Owner of Colorwheel Media Consulting

11) Seek new visual impressions and surroundings

They say that a change is as good as a rest, I have been a digital nomad since 2005, and when I am feeling stuck, I tend to seek out new impressions, this could be changing location, changing workspace, changing country… Whichever I feel is most beneficial at the time. If you stay stuck in one place physically, then maybe your mind is stuck in one place psychologically. Change your surrounding, look at something new, and your mind can follow with new thoughts.

 – Michelle Dale, CEO of Virtual Miss Friday

12) Remind myself of the “why” of my business

I start with watching Simon Sinek’s TED talk about the Golden Circle, in which he explains the power of “why” you do what you do. Taking your mind back to the reason you started your business in the first place, and what you envisioned your company to be, really helps to bring back your original passion and clears (at least for the afternoon) the day-to-day worries and nonsense that may be dragging you down.

Margot Bushnaq, Founder of BrandBucket

13) Rage Hard

As an Entrepreneur, I face many obstacles that get me into a funk or burn me out. When I just can’t get out of it, I’ve seen the best remedy is to go out with friends and party hard! Partying and raging with my friends gives me some time to completely forget about my worries and I come back a fresher me!

– Jeet Banerjee, Founder of StatFuse

14) Solicit Unwanted Advice

Tell someone else your woes and have them start making suggestions about what you should to and you will get so pissed off (thinking, “Who the heck do they think they are to tell me what to do?”) that you will often break through your funk.

Mark Goulston, Co-Founder of Heartfelt Leadership

15) Walk it Off

When I find myself in a mental rut, my first instinct is to power through it. But if I cannot power through it, I go for a long walk of up to 2 hours somewhere in nature. That does two things. It relaxes me, and more importantly, it lets thoughts flow, and I often come up with creative solutions to problems, or breakthroughs precisely on these kinds of walks. So in a way, if I am in a rut, deep down, I know that is good because it will force me to ultimately think more creatively and come out on top.

Alex Genadinik, founder of Problemio

16) Flip it Upside Down

I go upside down for a fresh perspective. Headstand or handstand or staying upside down on an inversion table lets you literally see everything from a fresh perspective. Being upside down slows your heart rate and combats stress, another pro for most entrepreneurs. And you don’t need to be an acrobat to do this. A simple down dog or just lying with your legs up the wall both also count as inversions.

Brett Larkin, Cofounder of GoalSponsors

17) Deadlift

When I have a short term mental block I deadlift. As a woman it is probably a little weird that “pumping iron” helps me think but having an activity that requires complete and total focus (you don’t want to fuck around with distraction when you are lifting more than your own body weight off the ground) allows me to let go enough of whatever was preoccupying me that when I come back to my work I’m able to see things in a fresh light.

Julie Fredrickson, CEO and co-founder of playAPI

18) Preventative Maintenance

Ruts happen because you drive in the same track every day. While it’s easier to have sameness (think Steve Jobs’ black turtlenecks) because decisions are stressful, you can pre-disorder your life by design. That means, at least for me, saying yes a lot more to uncertain and ambiguous ideas. It also means ignoring people who tell you to only do what you’re good at. (Hell, if you do that, how will you ever get good at anything else?)

– Dr. Janice Presser, CEO of  The Gabriel Institute

19) Push-ups!

Any time I have a bad call, get bored, or just need to change what I am doing, I drop down and do 30 push ups. I end up doing this 5-7 times every day and when I am out of the house for 14-15 hours a day, finding time to work out is not the easiest and this provides a nice way to get some physical work in while at the office. Also, being a leader in the office it shows that we encourage people to be themselves – even if it means randomly dropping down to do push ups!

– Bryan Silverman, Co-Founder of Star Toilet Paper

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Written by:
When Zach Davis isn't getting lost in the mountains, he is hustling from Boulder, CO as Tech Cocktail's Director of Marketing. He is the author of Appalachian Trials, a book chronicling the mindset necessary for thru-hiking all 2,181 miles of the Appalachian Trail, a feat he accomplished in 2011. Zach is a green tea enthusiast, die-hard Chicago sports fan, and avid concert-goer. Follow Zach on Twitter: @zrdavis.
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