My company, Drift, is the fifth one I've founded. Which means I've dealt with success, failure, new products, new people, acquisitions, scaling and more. I've seen it all. 

And almost a year ago, I pinned the following Tweet to my feed: 

"The hardest thing for an entrepreneur is not what you think. No one ever talks about it but this will make or break you. People? Process? Product? Nope. It's dealing with the emotional turmoil. Managing the emotional rollercoaster is the hardest skill you must master."

It was Christmas Eve, and we were gearing up to announce to everyone at the company that we were specializing the teams into business units--focusing on small, medium and large organizations.

I knew that we were turning the company upside down and it was going to cause a lot of pain. And looking back, it was way more painful than I predicted--and it took longer than I expected for it to turn rightside up again. 

Dealing with this emotional turmoil--and knowing that certain decisions might cause pain for the company and the people involved--is really difficult for me. But I also think that while growth phases are painful, the opposite is painful too. 

Here are a few things that have helped me deal with the emotional rollercoaster: 

  1. Talking to others (outside of Drift) who have gone through or are going through the same challenges, or reading about companies and people who have gone through periods like this too. Context is important and what I learn every time is that this pain is normal, and that's helpful to hear. 

  2. Practicing gratitude every day. There's an app I use every morning called "Day 1," where I write what I'm grateful for, what I will do to make that day great and daily affirmations. There are days where these will change and others where they repeat and become more of a mantra. 

  3. Practicing acceptance. If you've ever heard of the Serenity Prayer, it says this: "God grant me the serenity to accept the things I cannot change; courage to change the things I can; and wisdom to know the difference." I try to keep this in mind and practice acceptance every day. 

As entrepreneurs, there are going to be things we can control--and others we can't. And no matter what, there will be painful decisions to be made that won't always be easily understood. So when this inevitably happens in your company: 

1. Communicate as much as you can. I've found that the more transparent I can be, the better. You trust your people--and they should be able to trust you as well. 

2. Find ways to work through the emotional rollercoaster. I've shared the ways that help me--ways that have helped me after many years of dealing with this. But consider what works best for you and what will allow you to deal with the rollercoaster while still pushing you and your company to grow to be the best it can be.

Published on: Jan 28, 2020
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