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“Failing Forward” Is Bad Business Advice—Here’s What To Do Instead

I’m about to hit the buy button on a substantial purchase—a facilitator training I’ve had my eye on since last summer.

It’s a big move for my business and today feels like the day.

For a while there it felt like I would never not want to lay around crying over my brother Quentin’s death, hugging his ashes and making playlists for him.*

Weird time to make a substantial time commitment and financial investment, right?

But lately I feel like I’ve been shot out of a cannon. I have energy for everything and everyone. I’m scribbling down ideas in the morning and racing to my desk to move things forward that I have been stuck on how to move forward for a long time. I’m paddling again. This weekend I’m going on a third date with someone I really like, who I met at my brother’s funeral (yes, really!).

The 90s jam playing in my head all day long is Shine by Collective Soul → “Heaven let your light shine down.”

It is a testament to what is waiting for us on the other side of our pain.

If you are willing to sit with your discomfort and let it have its way with you, you’ll find it holds a depth of wisdom that’s difficult to find anywhere else. And yet grief isn’t something that’s discussed much in business circles.

But as business owners (and humans) we all feel it:

…when the offer you thought was going to be your next big thing doesn’t sell.

…when a business partnership goes pear-shaped, and you lose a collaborator and friend.

…anytime you let go of a business model that didn’t work or a dream you stopped believing in.

Because we are business owners and conditioned to take action, when the going gets tough we want to DO SOMETHING. Solve the problem. Create an action plan. Tackle the to-do list before the money runs out. Go for broke and hire a new coach!

Wait a minute.

Recently I was on a call with some business owners I’m meeting for a business retreat in Maine this week. One of them said, “I’m just in such a place of anger and frustration in my business right now, I can’t wait to be around smart people who can help me solve this stuff.”

The depth of her fear and disappointment was evident in her voice.

Wait, I wanted to say. Before we jump to problem-solving, let’s check to see what wisdom is there if we just sit with the sting of disappointed hopes a moment longer.

It’s not something many people are willing to do, but only because we haven’t been taught to. Grief isn’t a word you hear a lot in business circles. Instead you hear things like,

“Fail forward.”
“Everything is content.”
“Your mistakes are your greatest teachers.”

K, fine.

But those sentiments turn grief into a capitalist exercise: in order for it to be valuable, you must grow or learn something.

What if taking space for grief were an ongoing form of self-care—for you, your business, and for all the unprocessed grief in the world? It’s not as sexy as green juice and hot yoga, and it’s not as easily commodified, but it is no less critical. What if it were a gift we give ourselves so that we can become more whole? So that we can expand our capacity to feel even greater heights of joy and aliveness, in our business and our lives.

A huge part of grieving my brother has been about creating space for the rituals of grief, which my therapist Jen encouraged me to invent all on my own.

I watch TV with his ashes in my lap. I tend the poppy garden I planted for him. I polished his shoes and keep them by the front door, so he knows he is always welcome in my home. I started an archive of pictures, stories, and text messages that I revisit regularly. I connect with people in recovery who knew him. I read death memoirs to learn how others grieve. Jen calls these rituals “working the mourning shift.”

I know precious few people who have rituals like that for business grief.

I encourage you not to skip the mourning shift, to create your own rituals around business grief—and whatever other pains you are carrying, and we all have many. Before you jump to fix or solve, what if you sit with the feeling and see if any rituals emerge to help you stay with that feeling?

Be skeptical of anyone who tries to sell you a solution before acknowledging that grief and loss are as much a part of the entrepreneurial journey as beauty, freedom, and joy. They are simply another turn of the wheel, round and round in the circle game.

I promise you, no one is winning all the time no matter what their Instagram looks like. We’re all captives on the same carousel, to paraphrase Joni again.

Fuck failing forward.

Not all forward motion is progress. Constantly forcing yourself into productivity is a form of self-abandonment, and will not result in you being a happy, whole human. On the other hand, liberation is waiting for you the moment you release the need to turn every one of life’s hardships into a business growth opportunity.

Here’s to one step forward, two steps back 👣

Tarzan “Professional Stepper-Backer” Kalryzian

Tarzan Kay Kalryzian [she/her] Did someone forward you this email? ​Subscribe here​. Follow me on ​LinkedIn​.

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* Here’s a playlist for Quentin that my siblings and I collaborated on. Does not include any Collective Soul, sorry.

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