Blog Business and Leadership

Being in the Arena as an Entrepreneur Isn’t All Sunshine and Roses (But It’s Always Worth It)

When we moved into our new house over a year ago, I ordered a framed print on Etsy of The Man in the Arena quote by Theodore Roosevelt to hang in my office. 

I thought to myself, “This will help inspire me while I’m working!” 

I put it up on the wall and never looked at it again… until last week. 

Last week I read that quote and I bawled my eyes out. 

When you see an entrepreneur’s social media highlight reel and think it’s all glamor and being a fabulous “boss babe,” you are seeing a very small piece of the puzzle. 

(Side note: I do not use the term boss babe or really like it. I am a boss. No cutesy, feminine qualifier needed).

As CEO, I am responsible for 22 other human beings (i.e. full time employees). I take risks and make calls that have far reaching implications.

Last week, the leadership team and I made a decision that I knew would be controversial, but that I believed would be in the best interest of the entire team and our clients.

Because of some planned time off one of my leaders had, we decided that the only time we could roll out the change was the following Monday (only days away). This was a lot faster than I had in mind, but felt like the only option with calendar restrictions. 

I hosted a town hall meeting with the whole company to announce the change and address questions and feedback.

My expectation of this meeting was that it would be a fairly calm 30 minute conversation about the change, both the reasoning behind it and coordination of the logistics, with an additional 30 minutes just in case for questions.

The reality was 90+ minutes of me responding to feedback on a wide range of topics, concerns and grievances. Because the conversation went so far outside of what I had prepared for, I felt very much put on the spot.

As nervous systems reacted to the threat of such a large and sudden change, the meeting got increasingly challenging to facilitate and the feedback got a bit pricklier than I think it would have had people been feeling more calm.

Anonymous feedback (via a feedback form) was pouring in live with criticisms ranging from concerns about the change and timing (the topic of the meeting) to questions about pay, other people’s performances, and all kinds of things (not the topic of the meeting).

Many of the feedback items that were off topic for this meeting warranted a one on one conversation or at the very least a well thought out and intentional response on a different meeting.

Because of a miscommunication on how the feedback form would be used, anonymous feedback was unexpectedly read out to me LIVE on zoom in real time, and I did my best to answer each item as calmly, honestly and HR compliantly as possible.

Not all the feedback was off topic; there were questions and comments about the subject of the meeting. 

Many people on the team were understandably frustrated that such a big decision had been made without them (we make many big decisions collaboratively, which made this particularly jarring). 

They also had very legitimate concerns about the whirlwind timing of it going into effect (again, they are hearing this on a Wednesday and it is going into effect on Monday. The turnaround was very fast).

A point was made that I should have talked to certain people one on one about this change before the group announcement, and I apologized on the spot for not doing that because they were right. I should have done that and because of the time pressure and having so much on my plate, I didn’t even think of it until that moment. 

To say phase one of implementation did not go according to plan would be an understatement.

That meeting was one of the most challenging experiences I’ve had as a CEO (at least recently). 

I got off the meeting, gathered my thoughts, did a lot of neuro drills, and yes, cried to the man in the arena quote.

Once I was re-regulated, I was able to:

  1. Reflect on what went well and what did not go well around that meeting and the change rollout
  2. Make notes of things I will do differently next time
  3. See that while the implementation was bumpy, I still do believe that we made the right decision for everyone involved
  4. Be authentic with myself about the discomfort I feel around people being “mad” at me, disappointing others, etc
  5. Appreciate how far I have come as a leader in being resilient at times when I need to receive criticism
  6. Pat myself on the back for showing up, doing my best (even though it wasn’t perfect) and authentically acknowledging my mistakes publicly and apologizing

I chose these challenges when I stepped into leadership, and while the discomfort and mistakes aren’t my favorite part, the learning and growth that comes out of them is well worth it.

I want to be fully authentic about my mistakes and learning because I know it will help others and because being aware and open about failures is how we become better and help others rise with us.

I’m happy with the decision we made. I’m not happy with how it was communicated to my team, and next time I will do better.

To all of you out there who are making bold moves and doing your best, I see you and I’m proud of you. 

And in case you need an extra reminder that you’re a baddie, here’s the full “Man in the Arena ” quote by Theodore Roosevelt:

“It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat.”