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Entrepreneurs seated in chairs sharing strategies for optimizing wellness & productivity in startup culture.

Strategies for Optimizing Wellness & Productivity

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A recent survey of over 10,000 people reveals that 58% of tech employees experience “imposter syndrome.” Despite ample evidence of high achievement, workers feel unworthy, unintelligent, incapable or uncreative. At best, persistent self-doubt can stifle creativity, dampen passion, and decrease engagement. It contributes to absenteeism or presenteeism—when staff is present at work but performance has deteriorated—which disrupts team productivity. At worst, ongoing fears of being unmasked as fraudulent can develop into clinical levels of depression—a leading cause of lost productivity in the workplace. What can you do to ensure your well-being? How can you do to support the well-being of your team while maintaining productivity in your startup? Six founders share their key strategies for optimizing wellness and productivity. Learn practical behaviors you can implement immediately—and ones to avoid—to create a genuine culture of well-being.

Key Strategies  for Optimizing Wellness & Productivity

  • Don’t Glorify Unattainable Myths about Entrepreneurship

  • Stop Sending Mixed Messages about Self-Care

  • Practice Being Mindful

  • Prioritize Your Own Well-Being

Don’t Glorify Unattainable Myths about Entrepreneurship

Within the tech startup community, especially, a culture exists that glorifies overwork. The workaholism of iconic founders remains legendary. Serial entrepreneur Lara O’Connor Hodgson notes, “as founders, in the ecosystem we live in, we think it’s impressive to kill yourself working on your business.”

As CEO and President of her latest venture, NOW Corporation—a B2B payments company with an innovative revenue accelerator system for startups—Hodgson doubled her startup’s growth twice in four years. Like many founders, when starting her businesses, she felt pressured to “work 24 hours a day on my business. Or put the business off.” But she discovered that an “always working” mentality fails to optimize wellness and productivity.

Challenge the “Always Working” Mentality of Startup Culture

As founders, in the ecosystem we live in, we think it’s impressive to kill yourself working on your business. If you don’t put all that time in, you’re not committed. And I think that’s wrong.

Hodgson challenges, “no human being can do that and perform at a high level” over time. She’s right. Research shows that practices, like working through lunch or working 12+ hours per day hinder productivity and ultimately cost more as they lead to declining creativity, disengagement, and staff turn-over.

Taking Short Breaks Can Optimize Wellness & Productivity

A 2019 study of North American employees reveals that short breaks enhance engagement and productivity. Your staff needs to know it’s okay to take a break when they need to. As a founder or CEO, it’s especially important to take some time away throughout the day. While it sounds counterintuitive, taking a short time away from a problem can often provide greater clarity and insight. In the long run, that sparks motivation and makes you more productive. Hodgson emphasizes, “You have to have time away.”

Your best ideas don’t happen in a board meeting. Your best ideas don’t happen in a management meeting. And they don’t happen in a brainstorming session. They happen when you are nowhere near your office.

Reframe Your Definitions of Success and Failure in a Macro Context

Not only is a “never not working” mentality unhealthy and unsustainable, Andrew Dubowec, entrepreneur investor in early-stage technology companies, notes it’s shortsighted. Plus the results are often sporadic. Dubowec’s professional and personal experience gives him unique insights into wellness. Now VP of Strategy and Corporate Development at League, Inc.—a leading enterprise OS that is revolutionizing employee healthcare—Dubowec’s twelve-month battle with major depression prompted him to become an outspoken critic of poisonous myths that surround startup culture. He equates common but unhealthy practices—like working 100 hour weeks—with “sprinting ahead one day and doing 100 miles but then for three days, not being able to make progress.”

A desire to adhere to the unattainable myths of startup culture creates unrealistic expectations that reinforce unhealthy behavior. Crunchbase reveals that the average time it takes SaaS companies to reach IPOs is nine years. But Dubowec points out that many SaaS startups set unrealistic expectations of exiting in three or four years which can create unnecessary pressure on staff.

The reality is that great companies are built over decades, not overnight.   A lot of people who work 100 hours a week aren’t succeeding. The companies aren’t scaling. They’re not winning. And they can’t get the right people or keep the right people.

Don’t Allow Intense Periods to Set the Standard

A Stanford University study examining working hours and productivity validates Dubowec’s criticism of working excessively. Research shows that productivity per hour drops significantly at 50 hours per week. What can you do during those intense times—when you’re racing towards an inflection point or shipping a product—when the only way to deliver is to work 12+ hour days and weekends?

Matthew Bellows, a successful serial entrepreneur who has spent decades building and scaling three startups, acknowledges, “There will be weeks when you work 80 or 100 or 120 hours a week.” Before co-founding his third venture, BodesWell—a financial planning company—Bellows co-founded Yesware and WGR (Wireless Gaming Review) Media, Inc., which was acquired by CNET. Building a company entails intense periods of work that may consume your life, he consents, “there’s no silver bullet” but the key is don’t allow your actions during those intense periods to become your normal behavior.

There will be weeks when you work 80 or 100 or 120 hours. Don’t allow your actions during intense time periods to set the bar for normal behavior.

Statistics consistently suggest that working more hours doesn’t yield greater productivity, supporting Bellows’s advice. After studying work habits of business leaders, psychologist and behavior change expert Ron Friedman concluded that leaders who consistently overworked made poor decisions due to impaired judgment. Don’t get caught up in overvaluing the quantity of time worked. Instead, create a healthier and more productive culture at your startup by rewarding those who find ways to work more effectively. Lara O’Connor Hodgson explains, “a unit of time is not worth a dollar to me if there are no results.”

Stop Sending Mixed Messages about Self-Care

Many many startups offer perks, like unlimited personal time off (PTO), as a way to attract talent. But research shows that startup employees with unlimited PTO tend to take less vacation than employees with limited PTO. For some conscientious, mission-driven employees,  heavy workloads and time constraints make them feel guilty about taking time away. Others take cues from senior leadership. If the CEO never takes time off, it sends a message. Complete devotion to the startup—with no interfering personal responsibilities—becomes expected behavior.

Take Time Away

Fundamentally software is creative work. You need to be able to step away and clear your mind and do something else—to move your body and exercise or just travel.

Kevin P. Ryan founded multiple billion-dollar tech companies, including Business Insider, MongoDB, and DoubleClick. Business media dubbed him the “Godfather of Silicon Alley” for his influence on the New York startup community. Long before unlimited PTO became common in startups, Ryan decided not to set vacation policies for any of his companies. Vacations yield intangible rejuvenating benefits and, he reasons, technology enables us to check-in at any time, from any place.

I think everyone should take four to five weeks of vacation. I would rather have someone that works 47 weeks of the year pretty intensely.

Knowing that his CEOs will be influenced more by his behavior than by policy, he takes eight to ten weeks off annually now. Earlier in his career, he prioritized taking five weeks away every year. While Ryan advocates for vacation, he doesn’t go off the grid completely. Even while away, he checks in daily. “I do work every day, so I don’t disengage really almost ever. Every day I’m doing email, but if I’m skiing with my family in Europe until three in the afternoon and spend three hours doing email, and then have a great dinner that’s an incredible day.

Strike a Balance

While he endorses unlimited PTO, Ryan does not advocate a complete separation of personal life and work. He explains, “You can’t not work during all 48 hours of the weekend. I expect people to be on their email when they need to be. They have an operation to run, and so they do need to be in touch on that. The trains need to keep moving.” The goal is to strike a balance between working productively, to the best of your ability, and keeping yourself healthy.

Allow Autonomy

Empowering employees with some autonomy fosters inspiration. According to Harvard Business Review, inspired employees can harness discretionary energy. This makes them 125% more productive than an employee who is merely satisfied. Receiving an infinite task list and told when to do things can produce mental strain and cognitive load. Leadership should set clear priorities and targets. But building in some flexibility—allowing staff to manage their time—yields better results than micromanaging.

Kevin Ryan elaborates, “If you decide that Wednesday you want to take two hours because you want to go smell the flowers in central park? I don’t micromanage that. I know you worked on Sunday for a couple of hours. We’re not hourly workers, so I don’t track that. I don’t want to track that.

You need to get things done but you need to have an environment that you don’t burn out in.

Don’t Celebrate Unhealthy Behavior

Dubowec confesses that, even at League, leadership can “get caught celebrating people working on the weekend,” even though working through the weekend isn’t behavior the company endorses. He elaborates, “if leadership says, ‘here’s the hero of the week because they worked all weekend,” everyone looks at that says, ‘That’s the behavior I want to emulate.'” Being aware of your actions is the first step to changing them. 

We should celebrate people doing their jobs with excellence. But we shouldn’t celebrate people for the amount of time that they’ve worked.

Model Healthy Behavior

Setting aside resources or adding a line item in your profit and loss (P&L) statement are good steps, but a culture of wellness needs to be modeled to take root. Actions taken by leadership silently communicate more than paper policies. The personal behavior of co-founders and leaders demonstrates to staff that they are allowed to take advantage of the perks you offer. Bellows values vacations and takes them regularly, “not just because I need a break and I want to spend time with my family. But it sets a tone in the company.” When senior leadership models self-care, it creates a company-wide culture that enables everyone to thrive.

Practice Being Mindful

At Yesware, Bellows was careful to reinforce consistent messages to staff about prioritizing personal development and self-care. Backed by studies in management and entrepreneurship claim that mindfulness can boost innovationenhance intuitive decision-making and improve management skills, Yesware offered a variety of physical and spiritual training programs to encourage staff to take a break during the day.

Everything having to do with the company can be informed—or improved—by being  more mindful about it.

Be Aware of Everyday Habits

Despite his authentic enthusiasm for wellness and his experience practicing mindfulness, some of his unconscious daily behaviors communicated contradictory messages to staff. He laughs, “Don’t send emails at three in the morning.” He explains a scenario familiar to most entrepreneurs. “It’s the middle of the night and you either can’t sleep, or have a sudden insight that you want to communicate.”

As CEO of Yesware Bellows emailed his senior leadership staff in the middle of the night. While he didn’t expect a reply until the next morning, he learned that his team felt resentful and worried that they were expected to reply instantly.

It took Bellows a few months to discover the unintended sentiment that his middle-of-the-night emails provoked. He cautions that, even if you have an open-door policy, staff often feel reluctant to give direct feedback to the CEO about behavior. Practicing mindfulness and empathy can help you to notice small problems while they are still easy to solve.

He advises, “try to be a little more sensitive to what people are trying to tell you about what you’re doing. You are getting feedback if you pay attention to it.” Being mindful of how your actions affect your team in unintended ways and being alert for cues that provide feedback can make you a more effective leader.

Multi-Task Less

Most employee wellness programs aim to provide a greater balance between life and work. Hodgson challenges the outcome of that goal. Finding balance implies that you’ve managed to make things equal, she notes, which means “everything’s average.” She decries multi-tasking for similar reasons. Entrepreneurs wear many hats, so it’s tempting to try to maximize efficiency by multi-tasking—for instance, weeding their inbox or skimming a report while sitting in a meeting. She learned the hard way, “You think you are [being more efficient], but you’re fooling yourself.”

It’s really hard today. We are so distracted. It is so hard to focus when things are flying at you, emails and texts and buzzes and beeps. It really hurts our productivity. Because we go home thinking we multi-tasked, and we did everything only average.

Focus Your Attention

Instead of striving for balance and succumbing to multi-tasking—which leads to mediocrity— Hodgson advises other entrepreneurs to optimize time and productivity by focusing exclusively on the task at hand—whatever it is. “If I were at home with my son, doing what most of us do—which is think we multi-task—I’m doing nothing well. I’m pretending to engage. But I’m checking my phone. He knows this. And I’ve now spelled three words wrong in the email that I just fired off without really thinking about it.


You can optimize your time. If I’m in a board meeting, I tell people, “I’m going to come amazingly prepared, and for that two and a half hours, you have my undivided attention. You better use it well.” Because when I leave, something else has my undivided attention.

Prioritize Your Own Well-Being

Founding and scaling a startup is a marathon. The ability to take care of yourself is a big—if often overlooked—success factor if you’re going to endure for five or ten years it may take to grow your business. Hundreds of articles discuss common approaches to self-care help for entrepreneurs, with “create me time” and exercise daily most commonly cited.

Some advice—like get adequate sleep or find sources of fulfillment outside of work—offers little more than common sense. While other advice—such as taking supplements—can be contradictory. We can’t tell you what approach to self-care will work for you—There is no magic bullet or one-size-fits-all approach. But founders we talked with agreed on one thing: to succeed as an entrepreneur, you need to prioritize self-care and they share some practical tips on how to begin.

Identify What Matters

While some people advocate adding activities self-care—like coaching, meditation, or socializing—Kevin Ryan suggests that less is more. He emphasizes the importance of identifying priorities and cutting back—something he learned to value in his early thirties. As a father about to have a second child, he admits being worried about finding a way to balance work and family.

Set Priorities and Scale Back on Other Things

Many people continue to add activities to improve their self-care. But, a consistently busy social schedule can be more stress-inducing than soothing. Ryan reflects, “What most people don’t do is cut back.” Instead of trying to do everything, he reduced time with friends—watching sports and going to cultural events. “I cut those back 80% because you can’t do everything.”

You can only have a couple of priorities—maybe three—that I call A level priorities. For me, it was family, work, and staying in shape. If I’m not staying in shape, then other things fall apart.

Create Non-Negotiables

Hind Hobeika, co-founder and CEO at Instabeat, a revolutionary tracking device that allows swimmers to monitor their heartbeats and workouts in realtime, identified 3 pillars that mattered to her: sleep, food, and exercise.

Each became “non-negotiable” in the sense that she changes her behavior to accommodate those 3 needs. Because her first non-negotiable is sleep, she stopped using an alarm in the morning. Instead, her body wakes up on its own, around 7:00 am. Second, she elaborates, is eating healthy. She made the decision, “I will not grab quick fries just because I’m out of time. I’d rather not eat and wait to get a proper meal that’s consistent. I just stopped the mentality of ‘I don’t have time. Let me eat whatever’s in front of me.'”

Acknowledge & Honor Your Personality

Dulcie Madden, co-founder and CEO at Rest Devices, a startup that builds software and hardware for parents to help their babies sleep better, has a different approach. While most people embrace daily exercise as a mechanism for self-care, she confesses it didn’t work for her. She advises, “find out what works for you,” sharing, “I’m sort of an introvert, but I also draw really heavily off of other people’s energy.”

For Madden, cultivating a reliable network of mentors and friends going through similar experiences at hardware startups became a cornerstone of self-care. She formed a CEO group with three women she felt close to. Additionally, she gets advice from several investors who had different perspectives and experiences.

You don’t want to appear clueless. You want to be able to say, “Has this happened to you before? Is there a creative way that I can get out of this?” And then also have a peer who you can just throw all your feelings at—and they can throw all their feelings at you—because the CEO job can be a lonely job.

At its essence, self-care means having self-compassion. Lara Hodgson observes, “I think we have got to give ourselves permission to be true human beings. And it makes you a better CEO.”

Dos & Don’ts for Optimizing Wellness & Productivity







      • Take Time Away
      • Focus Your Attention
      • Reframe Your Definitions of Success and Failure
      • Cultivate a Supportive Peer Network
      • Find Meaning Beyond Your Business
      • Align Your Actions to Your Policies
      • Practice Mindfulness & Compassion
      • Don’t Buy into Unattainable Myths about Entrepreneurship
      • Don’t Work 24/7
      • Don’t Celebrate Unhealthy Behavior
      • Don’t Micromanage
      • Don’t Multi-Task
      • Don’t Send Inconsistent Messages 
      • Don’t Obsess over Failures 

Explore More

 Excessive Work & Declining Productivity

  • In “Working Too Hard Makes Leading More Difficult,” psychologist and behavior change expert, Ron Friedman shares findings of his study of work habits which revealed that leaders who consistently overworked made poor decisions due to impaired judgment. Exhaustion also led to interpersonal conflicts, weakening observational skills and overall communication, which damaged their effectiveness as leaders.
  • In “Great Companies Obsess Over Productivity, Not Efficiency,” Bain & Company partner Michael Mankins concludes that “by systematically removing obstacles to productivity, deploying talent strategically, and inspiring a larger percentage of their workforce, leaders can dramatically improve productivity and reignite top-line growth.”
  • In New Study Shows Correlation Between Employee Engagement And The Long-Lost Lunch Break, Alan Kohll, founder and president of TotalWellness, distills findings of a 2019 survey by Tork which reveals that millennials—the largest generation in the U.S. workforce—fear that taking breaks—especially lunch—signals a lack of commitment. The self-imposed pressure negatively affects their productivity, engagement and job satisfaction.
  • In “Is It Time to Let Employees Work from Anywhere?” researchers from HBS and Northeastern University discuss their findings that “work-from-anywhere” policies foster a greater sense of productivity and engagement.

How Personal Outlook Impacts Productivity at Startups

  • Impostor Syndrome Leaves Most Tech Workers Feeling Like a Fake,” distills results of a recent survey of over 10,000 people to reveal that over half of tech employees experience “imposter syndrome”—a nagging inner sense of being unworthy, unintelligent, incapable or uncreative despite ample evidence of high achievement.
  • The Imposter Phenomena,” presents findings of a study conducted on women professionals and demonstrates the commonness of feeling like a fraud in environments which are male-dominated. Today, 58% of employees at tech startups experience imposture syndrome regardless of gender. While “imposter syndrome” is not a pathological disease, it interferes with the psychological well-being of a person and negatively impacts productivity.

Personal Approaches to Well-Being

  • In Why Rest Is the Secret to Entrepreneurial Success, Aytekin Tank, Founder and CEO of JotForm, explores the roots of excessive work and shares how he learned that “being busy and successful are not the same thing … and how to balance work with restorative rest, our productivity can skyrocket.”
  • In “7 Strategies Every Entrepreneur Should Employ To Optimize Their Mental Health,” therapist and executive coach, Megan Bruneau, provides tangible ways that entrepreneurs can safeguard their mental health, such as “notice where expectations are ruining your life,” connecting with others and seeking help from a professional. In her podcast, The Failure Factor, she interviews entrepreneurs about how they coped with challenges and failures and ultimately thrived.
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