How Much Authenticity? When to Make Your Mess Your Message

How Much Authenticity? When to Make Your Mess Your Message.

Below is an article written by my long-time friend and business coach, Mike Krupit, founder of Trajectify. He discusses  the vulnerabilities that all of us have in one way or another and how they effect our business and professional life. He chose my story as of one of the three to highlight in the article. I hope this helps as you decide to Make your Mess your Message.

How Much Authenticity? When to Make Your Mess Your Message

Six weeks ago, I shared my coming out story in an article where I talked about how the coaching I’d received over the last two years had made it possible.

It was a piece meant to use my story to create inspiration for others when faced with uncertainty and the ensuing fear.

I could have continued in my career as a leadership coach, entrepreneur, and community leader without coming out publicly. I could’ve kept that part of myself invisible in my professional life. I’d kept it hidden for decades before in my personal life, so why not?

The lack of authenticity wears on us. It creates friction in our relationships and keeps them from reaching their full depth. Being authentic increased happiness — not just for me only, but for others in my relationships.

In her recent HBO Max series based on “Atlas of the Heart,” Brené Brown says that “our connection with others can only be as solid and deep as our connection to ourselves.”

I saw the value being more authentic had created in my personal life, and I wanted to bring that authenticity to my coaching.

Plus, the marketplace is demanding it. While some people may think the word is overused, the truth is: authenticity is in. Employees want it. Customers and clients want it. And for good reason — it makes our lives and our workplaces better.

I’ve been inspired by friends and clients who’ve done the vulnerable work of being authentic even in the face of fear.


In October 2020, my friend and Trajectify coach Chuck Hall was hospitalized with heart failure and kidney failure. Thankfully, he made it through. The experience prompted some serious emotional work for Chuck — he had to grapple with the fact that he hadn’t been to a doctor in 20 years and figure out what to do going forward.

Through work with a therapist, Chuck was diagnosed with complex PTSD from childhood and adult medical experiences. As he began to untangle the web of cPTSD, some other questions started coming up. In February 2022, Chuck was diagnosed with autism.

“Having PTSD didn’t seem as bad,” Chuck says, “because it was indicative of things that happened to me. Getting the autism diagnosis was really hard because it was about who I am. But the next day, I embraced the diagnosis and now see my autistic traits primarily as positives.” Complex PTSD is difficult to cure, but it is treatable. Autism — well, that is permanent.

Even so, Chuck shared his diagnosis on LinkedIn in late February. He’d already been talking about his cPTSD on the platform. Why?

First, Chuck wanted to be transparent and authentic with his clients and potential clients. “Often in my coaching, I’ll say, let me share an experience I had when I was at a similar stage of my career or when I had a similar problem. I’m not saying my client should do the same thing, but I think there’s something they could learn from my experience,” says Chuck.

When you’re asking someone to trust you and be guided by insights you’ve gleaned from past experience, they’re looking for transparency and authenticity. “I want people to know about me as a coach,” he says.

Chuck also wanted to do more than pay lip service to the concept of destigmatizing mental health issues. “We need to normalize people getting help for whatever mental health conditions they have and being accepted for whoever they are,” he says. “It’s not enough to say that we support people who are diverse. We have to get to that higher level of helping people know they belong.”

For Chuck, part of that work is creating spaces where people who are neurodiverse have an opportunity to work with a coach who’s also neurodiverse. “They may never have felt comfortable working with a coach before because they didn’t think a neurotypical coach would understand them.”

So what has the experience of sharing his diagnosis been like for Chuck?

If anyone’s been turned off by it, they haven’t told him about it. And, he says, he wouldn’t really care. What’s been wonderful are the people who’ve reached out because he’s opened a door for them to explore PTSD or autism, and they have questions.

The autism diagnosis and sharing it with his professional community haven’t changed Chuck’s method of coaching, though he thinks reprocessing past experiences in light of his autism diagnosis has made him a better coach. He’s more attuned to instances where communication styles don’t match up or where someone’s words didn’t convey their true meaning, something he can help clients begin to notice as well.

It’s also given Chuck a new framework for understanding why he is the way he is — including as a coach. One of the things clients have appreciated about him over the years is the direct way he offers his thoughts. Now he sees it as the “autistic trait of calling shit out.”

See: The Most Common Limiting Beliefs of Entrepreneurs and How to Overcome Them


Not all of our authenticity is as dramatic as coming out as gay or as autistic.

Sometimes it’s just about showing up as your whole self and finding the places where you can create a connection with another human being.

My client Fred Poritsky started a new career at 60 years old. He’d spent his working life in accounting and then as the executive director of a synagogue. Now, Fred told his wife he was going to start a web design company.

“To this day, I’m still shocked that people hired me,” he says.

In the beginning, Fred was nervous about the things that set him apart from most of the other people in the web design field. He was 60, not 25. He hadn’t come up in the tech world.

Maybe people wouldn’t want to work with someone like him.

I coached Fred in those early days of his business, and it didn’t take long for him to see that the things that looked like problems were actually effective ways to differentiate himself.

He had decades of business experience and the ability to build strong professional relationships. He knew what the issues were for professional services firms, non-profits, and religious organizations that could use his services because he’d worked in them.

Plus — something most people can’t say — he’d played the drums in various bands for 50 years.

Fred started sharing more of his story, and that sharing created connections. “I’ve met so many people that still play a little bit, they have the drums in their basement, or they were sad that their mother sold them,” he says. “It always creates a conversation.”

So does his later-in-life career change. Fred gave a presentation at a coworking space, and a woman approached him afterwards. She’d been feeling stuck in her career and like she was too old (at 49) to make a big change. Fred’s talk inspired her to go after the career she’d always wanted.

Embracing the things that set him apart in his field has helped Fred build long-lasting relationships. He’s kept almost all of his clients over the last nine years, which isn’t the norm in the web design industry. He’s been himself, which allows people to put a lot of trust into him and his services.

“I’m not Fred the drummer, Fred the accountant, Fred the web designer. I’m Fred — it’s all the same person. I think people see that.”

See: Five Strategies for Overcoming Imposter Syndrome as an Entrepreneur


Our stories evolve over time, especially when we’re growing. What we may see as our authentic self becomes outdated as we gain new experiences and expand our comfort zones. Who we are and how we feel today might not be who we previously thought we were. We’ve since gained new competencies and increased confidence.

In an article for the Harvard Business Review, “The Authenticity Paradox,” Hermenia Ibarra writes: “…the stories can become outdated as we grow, so sometimes it’s necessary to alter them dramatically or even to throw them out and start from scratch.”

She concludes that “revising one’s story is both an introspective and a social process. The narratives we choose should not only sum up our experiences and aspirations but also reflect the demands we face and resonate with the audience we’re trying to win over.”

Chuck doesn’t get less autistic. Fred doesn’t get less old. I don’t get less gay. Yet our story evolves from those identities as each of us grows from where we are today. We become known, perhaps, as world-class web designer, award-winning coach, or community builder and leader. Be it such accomplishments, or new trauma or new perspectives, we change and our story continues to develop as we gain experiences.


Philadelphia marketing strategist Cathy Goodwin published a podcast episode last year titled Business Storytelling: Your Mess is NOT Your Message.

In it, she makes a number of excellent points:

Sharing your vulnerabilities is risky. It may turn some people off.

Sharing something unpolished and cringe-worthy while you’re in the midst of a mess is…messy.

Sharing too much vulnerability when you’re just starting out can undermine a confident image.

I think those are all the reasons to be intentional and thoughtful about making your mess your message — not to avoid sharing those vulnerabilities at all.

I didn’t write a LinkedIn post about who I was now sleeping with. Chuck didn’t unpack a therapy session on his LinkedIn page. Fred didn’t sit down while his business was still brand new and write about how scared he was that no one would want to hire him.

Being vulnerable and authentic in your professional life doesn’t mean that you broadcast everything that’s happening while it’s happening on a public forum. It’s about choosing to make visible — after you’ve processed them for yourself — those things that could have remained invisible and that offer opportunities to connect with others. For them and for you.

Your life and your business will be better for it.

Founder of Trajectify

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