The (Strange) Case for Embracing Pain in Your Business

The (Strange) Case for Embracing Pain in Your Business

Full Steam Ahead

In December 2017, I gave myself a gift I dreamed of for years: I started my own coaching business. I was thrilled that I’d be doing work I truly enjoyed. Writing, teaching, and creating unforgettable experiences to help creative women build the business and life she truly wanted. Yes, sign me up 1,000 times over.

I saw a smoothish road ahead of me, with a few bumps, but that’s to be expected. Then, as the weeks passed, the bumps turned into potholes. And that smooth road turned into a dirt, footpath running through a tangled forest. The marketing tactics that failed to meet goals. The email list that wasn’t growing fast enough.

I muddled through doing what I’ve always done in these situations: obsessively researching and planning my way out of confusion. I’d scour Google for hours finding a new strategy that promised perfect peace for my business, see some results and feel secure. Only to be confronted with another unforeseen challenge and setting off on the same cycle all over again. Every time I found myself planted in the security of my “success”, I would get uprooted yet again.

Triumph. Defeat. Google. Repeat.

If only I could learn how to keep the seesaw up, at all times, I’d be golden. So that is exactly what I sought to do. I was on a constant hunt for the right strategies that would ensure I had a business with zero problems. Or at least only the pretty problems like too much website traffic or a massive waitlist for my group coaching program. On and on the hamster wheel I went.

And then, in July 2018, my family suffered a heartbreaking loss. Now I wasn’t just feeling uprooted in my business, but also in my personal life. And remember, friend, when I feel uprooted, I research and plan my way through it. So, I hunted for some inspirational spiritual books that would give me the tools to get through this difficult time.


“I was on a constant hunt for the right strategies that would ensure I had a business with zero problems.”

The Book That Changed it All

But this time, I got way more than I bargained for and exactly what I needed.

I can’t tell you why I decided to buy a few books from a white, middle age, Buddhist nun named Pema Chodron. Maybe because I listened to a snippet of Pema Chodron’s interview with my soul-sister, Oprah. I can’t really tell you why, but I was drawn to what Pema Chodron had to say about pain, fear, and life’s challenges.

Within reading one page of Pema Chodron’s book, I knew my life was going to change. On the first page of her book, The Wisdom of No Escape, Chodron writes:

“There’s a common misunderstanding among all the human beings who have ever been born on the earth that the best way to live is to try to avoid pain and just try to get comfortable…If we’re committed to comfort at any cost, as soon as we come up against the least edge of pain, we’re going to run, we’ll never know what’s beyond that particular barrier or wall or fearful thing.”

Wasn’t I running from pain every time I faced a new challenge in my business? Wasn’t I avoiding seeing what was beyond the fearful thing I tried to research and plan away?

The Spiritual Crossroads

I was raised to believe that the point of life was to create as much pleasure as possible and avoid all the pain that you can. Bored? Read a book. Unhappy? Buy something. Hurt? Yell at someone. Confused? Google. Sure, all of those coping mechanisms made me feel better, but only for a short time. No matter what I did, the pleasure never lasted and the pain would always catch up to me. If what Pema Chodron wrote was true, then everything I was taught had to be upended.

Reading Chodron’s book was like standing at a spiritual crossroads. Keep running away from pain, no matter the cost? Or learn to embrace the pain that is a natural part of life and see what happened?

I decided to choose…

Wait, a minute! Why would anyone in their right mind embrace pain? What the hell does that even mean? I can’t tell you what embracing your pain feels or looks like. Maybe your particular flavor of running looks like mine. Research and plan obsessively to avoid feeling the overwhelming sense of panic that things are out of your control, no matter how much you’ve planned. If I wanted to live deeply, which I did, then I would have to learn how to stay open when that panic came.

Why My Business Changed

I did. And it felt horrendous. It still does. But the consequence is that my all-consuming desperation to get solid footing underneath my business, my family, my entire life, feels a little less all-consuming. Learning to feel my pain also helped me enjoy pleasure. I don’t have to cling to the highs so fiercely knowing that the good feelings wouldn’t last. In equal measure, I  don’t have to catastrophize pain because just like the good feelings, the pain doesn’t last.

More powerfully, embracing painful feelings has helped me show up more confidently and generously in my business. I can give to my clients without obsessively worrying about my own triumph or my own demise at every turn. Which is exactly what I wanted when I started my business in the first place. Instead of worrying about where the next success will come from and how I can dodge the next setback, I get to settle into the experience I’m having right now. In this moment.

I get to answer honestly, what I’d do knowing that I will laugh and cry on this crazy journey called entrepreneurship.

What Will You Choose?

Now, I want you to imagine you’re standing at the same crossroads I was. You can continue to search desperately for the idea, the job, the feature, you name it, that will ensure you never have to hustle, impress, or feel bad ever again. Or you can learn to lean into every single feeling that you have, good or bad, pleasure or pain, and see what you can create. Which one do you choose?


Danielle CallendarDanielle Callendar is a soul-fueled business coach at Chantiluke ( She helps creative, multi-passionate women transform their lives from the inside out so they can start their very first business.