Struggles Are a Part of Leadership

Back five or so years ago, when I was CEO at Merchantry, there were times I didn't want to go into work. How depressing is that? At times it really drains your energy to push the ball up the hill every day...especially in the face of dwindling funds, customer cancellations, company restructuring - it saps your energy. #thestruggleisreal

What does it mean if the CEO doesn't want to come into the office? Does it mean the company is doomed? These are all thoughts that sometimes ran through my head. It's normal. Over time, I've come to learn that even a leader is not immune to bad days from time to time. Or a stretch of bad days!

It's normal and part of the journey. If you're not experiencing these kinds of feelings, there is likely something wrong with you.

“I abhor the grind but there’s some Sisyphus in all of us, I suppose.” - That’s wisdom from Ralph Harmon, and he’s right. At the time I didn't know what to think. Luckily I did find a few close friends to share with. I put too much on myself thinking I had to be the one to find a way out of this. Lean on your support network - in particular other CEOs. Your family. Close friends.

Talk to them honestly about what you are going through and stop and listen to their stories as well. You might learn you are more inspiring than you think you are.

Nicolas Derico asked how I kept my employees “switched on” during these times. I think communication and as much transparency as possible is important. MOST importantly with your critical employees. You probably know who your "linchpin" employees are - the influencers and leaders who command respect and who other people look to for their cues. You need to ensure you are constantly in touch with these people to let them know "the real story" of what's going on. Lots of information in companies is not transmitted formally - it's done informally and via back-channel. Don't ignore these avenues.

When I initially posted this on LinkedIn, I got a lot of responses from other folks who understood this struggle from their own experiences.

Joe Kovacs shared the following: “The roller coaster (of emotion) is real! I think it has been super valuable to have partners in the business I can trust. We are walking a shared journey. I think sometimes in leadership we and others can put impossible expectations on ourselves to always be on. I agree that bringing authenticity to the role is so helpful. We have have been able to create a healthier culture where people can share the highs and lows of their journey and get support in times of need. It takes accepting and valuing that we are all people with needs and not cogs in a machine.”

Tommaso Trionfi said “Being a CEO is a burden you have on your shoulders all the time. You cannot take it off for a few days, good or bad.” Absolutely. That can get to a person, it’s part of being human. It takes a toll, but it also invites opportunity to flex your resilience, or as Walter Holbrooks put it, “Mental Toughness: getting through bad days, kicking down roadblocks and reaching another plateau.” Amen.

I hope this post gives other entrepreneurs some perspective on their own journeys.

Rick Watson

Rick Watson founded RMW Commerce Consulting after spending 20+ years as a technology entrepreneur and operator exclusively in the eCommerce industry with companies like ChannelAdvisor, BarnesandNoble.com, Merchantry, and Pitney Bowes.

Watson’s work today is centered on supporting investors and management teams incubating and growing direct-to-consumer businesses. Most recently, in partnership with WHP Global, Rick was a critical resource in architecting the WHP+ platform, a new turnkey direct to consumer digital e-commerce platform that powers AnneKlein.com and JosephAbboud.com.

Watson also hosts a weekly podcast, Watson Weekly, where he shares an unbiased, unfiltered expert take on the retail sector’s biggest players.

In the past year alone, Rick has spoken at many in-person and virtual events as well as podcasts on topics ranging from retail/ecom to supply chain/logistics and even digital grocery including CommerceNext IRL, ASCM Connect, and Retail Innovation Conference.

https://www.rmwcommerce.com/
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