Challenges

8 Entrepreneurs Share Their Best Advice for When the Going Gets Tough

How should you respond to adversity?
8 Entrepreneurs Share Their Best Advice for When the Going Gets Tough
Image credit: David Lees | Getty Images
Guest Writer
VP of Strategy with Freshbooks
7 min read
Opinions expressed by Entrepreneur contributors are their own.

Despite the "overnight" success stories you read about in glossy business magazines, the overwhelming majority of successful businesses take years, if not decades, to build. It's never easy. Entrepreneurs often ride a roller coaster of highs and lows that feel even more intense because they're running the show. Steve jobs once said, "I'm convinced that about half of what separates the successful entrepreneurs from the non-successful ones is pure perseverance."

I asked a few highly successful founders to share their advice for other entrepreneurs going through a rough patch. Here's what they shared.

Related: How 5 Entrepreneurs With Household Names Turned Failing Businesses Into Successes

 

8 Entrepreneurs Share Their Best Advice for When the Going Gets Tough

Reconnect with your "why."

Reconnect with your "why."
Image credit: Courtesy of ClassPass

"It's easy to get sucked into the minutia of the day-to-day tasks of building a business, so take the time to get back to your inspiration and reconnect with your mission and vision. Going back to your 'why' can help shift your mindset since it's the only thing that matters." -- Payal Kadakia, ClassPass Founder and Executive Chairman

8 Entrepreneurs Share Their Best Advice for When the Going Gets Tough

Don't sugarcoat things with your team.

Don't sugarcoat things with your team.
Image credit: Courtesy of WePay

"For an entrepreneur, it's important to remember that it's not just about you, but about your whole team, too. Your team can either be one cohesive unit that helps you get through a challenge, or they can become frantic and frustrated -- making the situations worse and harder on you as a leader. When addressing low points, you should be honest with your team and not sugarcoat anything because they will understand what's happening. At the same time, you should express context for those challenges, optimism about the long run, and where you ultimately want to end up. If you do that well, your team will come together, stick with you through the tough times, and bring a lot of energy." -- Bill Clerico, WePay CEO and Co-founder

8 Entrepreneurs Share Their Best Advice for When the Going Gets Tough

Imagine someone else in charge.

Imagine someone else in charge.
Image credit: Courtesy of Upstart

"I find that when I hit a low point in our business, I lose brain cycles to questions such as: How did I get here? What could I have done to prevent this? Am I good enough to solve this problem? It makes it hard to figure out a path forward. I have a little hack that helps in these moments. I imagine what would happen if someone I really admire took over my job tomorrow. It helps to picture someone I know well, someone with whom I've worked. I ask myself, what would this person do, and what would the outcome look like? I write it all down. Then I just go do it." -- Anna M. Counselman, Upstart Co-founder and Head of Operations

Related: Do These 50 Things Regularly and You'll Become a Better Entrepreneur

8 Entrepreneurs Share Their Best Advice for When the Going Gets Tough

Keep a positive mind.

Keep a positive mind.
Image credit: Courtesy of AppDirect

"I believe strongly in the value of Positive Mental Attitude (PMA). Building a business is certainly not easy, but you can never underestimate the importance of positivity as a means to effect change. Staying close to your values and focusing on the end game, not the short term, helps to keep you pushing forward in those rough patches." -- Daniel Saks, AppDirect Co-CEO and Co-founder

8 Entrepreneurs Share Their Best Advice for When the Going Gets Tough

Lean into the discomfort.

Lean into the discomfort.
Image credit: Courtesy of Hello Alfred

"Many extraordinary athletes love to compete more than they love to win. Keep that attitude about the journey of building. Failing is absolutely necessary to be successful over the long term. There aren't shortcuts, and it's going to be hard. Instead of trying to avoid the discomfort, be brave and lean into it. Say, 'I failed!' and let yourself embrace whatever emotions come with that. These feelings are important because they motivate us to try something harder. Once you've done that, you can put blame and your failings aside and try to understand what made you fail. Then own it. Take responsibility. It's a beautiful, unique lesson that only that scenario could teach you. Reflect and learn from it." -- Marcela Sapone, Hello Alfred CEO and Co-founder

8 Entrepreneurs Share Their Best Advice for When the Going Gets Tough

Find people who can relate.

Find people who can relate.
Image credit: Courtesy of Shippo

"No one tells you how hard it is to be a founder. From the outside, everything looks like an overnight success and everyone is always 'crushing it.' But, it's simply not true. Success is a rollercoaster, and the ride doesn't end. I've found having people to talk to and relate to has shown me that the emotional ups and downs are normal.

"Talk to people who can relate and will listen without judgment. Founders always seem to appear as if they have all the answers, but if you find others you can trust and have honest conversations with, you'll find you're not the only one having challenges." -- Lauren Behrens Wu, Shippo CEO and Co-founder

Related: 8 Hugely Successful People Who Didn't Graduate College

8 Entrepreneurs Share Their Best Advice for When the Going Gets Tough

Surround yourself with the right people.

Surround yourself with the right people.
Image credit: Courtesy of FreshBooks

"In the company's first two years, we were working from my parents' basement with about 10 customers each paying us $10 a month. I was taking business calls from a furnace room. All the signs were there that we were failing, and I was close to calling it quits. I remember glancing over at my co-founder Levi, coding away at a desk and bobbing his head to some tunes.

"He was totally loving what we were doing, what we were building. I remember thinking, There's a guy who's way smarter than me, and he's all in. I knew if I were to ask him how things were going, he'd say, 'Mike, we had seven people try the product today, that's amazing, right?'

"That kind of positivity kept me going in the early days. What I can offer is this: When you're having that kind of self doubt, surround yourself with people who will inspire you and keep you going." -- Mike McDerment, FreshBooks CEO and Co-founder

8 Entrepreneurs Share Their Best Advice for When the Going Gets Tough

Know that there is no perfect plan.

Know that there is no perfect plan.
Image credit: Courtesy of Drift

"Keep moving. Even if you're not 100 percent sure what to do, make something up. In the early days of a startup, it can feel like you're wandering through the desert. So imagine you're there and you look 360 degrees around and everywhere you look you see the horizon. It looks the same in every direction and there are no landmarks that you can go toward. There's no obvious way out of the desert, and you don't know if you're moving forward or you're moving backwards, moving to the left or moving to the right. In other words, you don't know if what you're doing is getting you closer to your end goal or getting you further away from it. In these cases, you have to make it up.

"It's not an answer that people want to hear, because for most people, building a business is about having a plan and an excel sheet and a formula that can predict everything. But, in the early stages, you have to recognize that you're going to have to make some best guesses and maybe some of them are based on intuition. And then based on those guesses, you're going to set some goals -- like the number of steps you walk each day. Whatever your goals are, you're going to make them up and you're going to set daily, hourly, weekly goals that you can achieve. That's how you get out of the desert." -- David Cancel, Drift CEO and Founder

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  • 8 Entrepreneurs Share Their Best Advice for When the Going Gets Tough
  • 1. Reconnect with your "why."
  • 2. Don't sugarcoat things with your team.
  • 3. Imagine someone else in charge.
  • 4. Keep a positive mind.
  • 5. Lean into the discomfort.
  • 6. Find people who can relate.
  • 7. Surround yourself with the right people.
  • 8. Know that there is no perfect plan.
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