How to embrace ‘entrepreneurial thinking’ even if you’re not an entrepreneur

As an entrepreneur, I know a few things about coping with chronic uncertainty. During COVID-19, this type of thinking is especially useful.

How to embrace ‘entrepreneurial thinking’ even if you’re not an entrepreneur
[Photo: Mikael Kristenson/Unsplash]

I think it’s fair to say that we’re living through a time of peak uncertainty. Several months into the COVID-19 crisis, we still don’t know how long we’ll have to socially distance, or what our new “normal” will look like. It’s unclear what kind of long-term impact this will have on our economy, and millions of people don’t know when, or if, they’ll be back to work.


It’s a lot to handle. I certainly don’t know how everything will unfold, but I do know a few things about coping with chronic uncertainty.

As an entrepreneur, I live with the reality that my business could close at any time. I work under the assumption that things could go sideways within a matter of months. While COVID-19 has obviously heightened my vigilance, my fears around keeping my business afloat were a big part of my life before the pandemic.

The irony, of course, is that as CEO of a company with over 100 employees, it’s my job to create a sense of security for my team, even though my reality is contending with the stress of uncertainty every day. Throughout my journey I’ve realized that learning how to deal with uncertainty isn’t just an important part of running a business—it’s a critical life skill that’s too often overlooked.

Whether you’re an entrepreneur, newly laid off, or simply struggling to cope with the extraordinary stress we’re all experiencing right now, here are a few techniques I’ve learned over the years that have stopped fear of the unknown from taking over my life:

Learn to wrangle your thoughts

Humans are hardwired to hate uncertainty. Research has shown that being sure something bad is going to happen—for example, knowing you’ll definitely be late for a meeting—is less stressful than worrying whether you might be late. But my experience has taught me that spending every day contemplating the unknown is a surefire way to lock yourself into being mentally exhausted and chronically stressed.

Several years into running my business, I started to practice meditation and mindfulness as a way to focus on the now rather than on the future. One book that really helped me was Why Buddhism Is True, by psychologist Robert Wright, which explains the Buddhist belief that worrying about the future sets us up to suffer twice—once before anything has happened, and again if something bad actually happens. Incorporating meditation and mindfulness into my life has helped me gain control of my own thoughts and break out of this destructive habit.


I’ve also learned to use a few “compass” questions to orient my thoughts toward what I can control. When I find myself fixating on uncertainty, I try to stop and ask myself: What is important to me now? What am I worried about? What do I need most?

I’ve found these three simple questions ground me in the present and help me figure out what action I can take today, rather than becoming paralyzed by a fear of tomorrow.

Don’t pretend you’re an island

When it comes to building a business, most entrepreneurs learn quickly that you can’t do it alone. I’d be nowhere without the mentors whose advice helped me along the way, or my core group of friends whom I trust for honest feedback.

I’ve also learned, through trial and error, that I don’t have all the answers for every problem or question I face—in business or in life. So I’ve built a habit of asking the people around me for input. A former colleague, for example, suggested I hire a values coach when I was trying to figure out how to make some big shifts in our company culture. That tip proved to be a game changer, both for my team and my personal development.

In dealing with the impact of COVID-19, asking for help might be a little more practical, like speaking to your accountant about financial concerns, or taking advantage of government support or funding. If you’re a business owner, it might mean asking your employees for their ideas to keep revenue coming in during the downturn. And definitely turn to trusted friends or family for help if you’re feeling emotional distress.

Dig deep and be generous

One of the most heartwarming trends to come out of this crisis has been story after story of independent entrepreneurs stepping up to support their communities, even while they struggle to stay in business. We’ve seen breweries making hand sanitizer and fashion designers making face masks for medical workers. In my spare time, I’ve been helping some local restaurants in my neighborhood get set up for online orders, after they gave free food to front-line healthcare workers.


Entrepreneurs know that our livelihoods depend on support from our communities, and we have a responsibility to provide it in return. Especially in times such as these, being generous and offering help where it’s needed can cement meaningful connections and generate goodwill. And you never know what kind of opportunities those will lead to down the line.

Absolutely, a lot of people are struggling right now, but finding even a small way to give back can help strengthen your community—and strong communities are key to getting us all through this.

Don’t get hung up on failure

We’re living in an extremely difficult time, and hard work alone can’t ensure success. You also need favorable conditions to support it. If, despite trying your best, you’ve had to hit the reset button—whether that’s closing your business, living through a layoff, or having a reduced income—know that it’s likely not your fault.

Setbacks are inevitable for many people in times such as these. As devastating as it is, losing a job or a business is also a chance to reflect on your work and potentially find new opportunities through remote work or a newly discovered hobby or skill.

The thing about uncertainty is we just don’t know how things will ultimately shake out—for better or worse. There is just as much chance things could wind up for the better, though that just might mean shifting your definition of “success.”

Ben Crudo (@bengmn) is CEO of Diff Agency. A retailer turned technologist, Ben is an e-commerce expert helping retailers win today and tomorrow.