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How to ‘Normalize’ Challenges

In growing a business, one of my biggest struggles was overcoming the idea that things should be easier. There’s always a problem to solve — here’s how I came to terms with that.

Entrepreneurship is hard. It’s no secret that founders and CEOs are at higher risk of burnout; studies have shown they’re also more susceptible to mental health issues. Growing a business and getting a foothold in the market — especially if you’re responsible for other people’s livelihoods — is difficult.

I spent my early days as an entrepreneur buzzing around, mastering business development and trying to convert every marketing expenditure into a sale. I got in the trenches with developers and spent numerous hours with vendors. I talked to other entrepreneurs about their struggles and took notes, applying immediately what I could to solve my own.

But I realized, after years of doing this, that I was never going to get what I was really looking for. I was doing all this legwork and research in the hopes that, if I solved enough problems, there would eventually be no more problems to solve. Everything would be smooth sailing.

That’s not reality, however, and I had to come to terms with it — for my sake and my team’s.

Challenges Are Normal

Our society has a tendency to normalize ease. Yes, pop culture has popularized drama in the form of “reality TV” and tabloid reporting. But in real life, people have grown accustomed to convenience. Our need for instant gratification can overwhelm our desire for quality or depth. Software updates and endlessly updated versions of products assure us that other people will solve problems quickly so we don’t have to experience them.

All this accommodating has a darker flip side: We’re more easily frustrated when things don’t go the way we planned. By coddling ourselves, we’ve come to (unrealistically) expect calm at every turn — friction is an unwelcome distraction that delays our ability to get what we want. We come to see it as a nuisance, a thing to be endured and then forgotten.

But psychology tells us that the struggle is the journey. By overcoming obstacles, we strengthen our vision and our skill set, finding smarter ways to carry out our tasks. By working on skills gaps, we develop well-rounded teams. By surviving incredibly difficult market circumstances or industry downturns, we become more resilient and less wary of what’s to come. Confidence can’t be bought, and it’s something nearly all of us could use more of — and that’s what challenges can provide.

I realized that my longing for calmer times was setting me up for failure. Entrepreneurship does contain periods of calm mixed in among the hectic or stressful times, but to want that as my norm? Well, I shouldn’t have pursued entrepreneurship if I wanted everything to follow a straight line. If I still wanted to lead my own business (and I did), I had to find a way to reframe my perspective. Here’s what I did:

1. At every weekly meeting, I asked my teammates what they were a) really excelling at and b) struggling with.

I didn’t want my team members to feel they had to be perfect to work at my company, and I was afraid my exasperation about problems, big and small, may have given them that impression. I made it a point to have all of us celebrate something we were doing great at in front of the team — everyone needs support to keep on keepin’ on. But I also wanted us each to “show our flaws” by discussing something we were trying to work through. Sometimes, teammates had great suggestions to implement; other times, they simply commiserated because they’d been there.

2. I started asking more questions.

I don’t have all the answers, and expecting that of myself — just because I was the CEO — was silly. I made sure my team saw me backtrack to fill in gaps in my own knowledge: How did we handle that issue the last time a client brought it up? Do you guys think we need to more explicit when we define “diversity” at client meetings? What price point has been making prospects shy away on calls? Having more data made me feel confident that I was making informed choices, wrong or not, and that calmed me. It also resulted in more companywide information sharing, which helped everyone feel more prepared.

3. I walked through worst-case scenarios.

It turned out that one of the reasons I was so exhausted by every problem that cropped up was that I worried how I’d manage several at once. What if I didn’t resolve one issue before another came, and then another, and they snowballed to have a crippling impact on the company? I immediately jumped to catastrophe. As I worked on shifting my mindset toward problems, I started making myself ask questions that would lead to the worst possible outcome for any of these issues. If that client didn’t renew, what would our revenue look like? If he complained to another client, what could happen? If the economy crashed and people didn’t need our main services any longer, what would we do? Considering every contingency and developing back-up plans reassured me that my team could get through anything if we just created cushions.

4. I delegated more.

This may sound like crazy talk — isn’t controlling situations the best way to defuse problems? I discovered, however, that I was taking too much on by trying to remain in control of everything. This was fostering my feeling of being overwhelmed, and I got the sense that my team had some fear about my stress level, combined with their lack of involvement. What was I so worked up about? By letting them in on tasks and projects that would help them grow, I was doing us both a favor. We also got to develop solutions together, which decreased stress on both sides.

While achieving your goals and coasting sounds delightful, it’s simply not realistic as a leader. There will always be something. By strengthening my own outlook and letting my team help me out, I found ways to get us all more comfortable with challenges. Not only am I no longer scared, but I’m no longer exhausted, either — and that gives me the energy to tackle whatever comes my way.

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