The Great Email Mistake of 2022: When I accidentally asked the wrong person to be my mentor
sign displaying the word "Ask"

There was no shortage of face-palm moments in 2022, but this one takes the cake…

As a #leadershipcoach I know all too well about the importance of having #accountability partners. Towards the end of what felt like a really challenging, yet not so rewarding year, I decided it was time to level-up and find a new #mentor.

I’ve been fortunate to have several amazing formal and informal mentors over the last 15 years of creating and growing my business. It was time to find someone with the right combination of #wisdom#experience#success, and most importantly, someone I feel safe being #vulnerable with, to help me face my current #challenges.

Admitting to yourself that you need help is one thing, actually asking for it is another. Deb, the amazing leader I eagerly aspired to learn from, entered my life at the tail-end of 2021 and we rapidly bonded. It just so happens that soon after we became thick as thieves she co-published the book, Got To Help: 31 Strategies to Offer, Ask For, and Accept Help. Cue Alanis Morissette. So after a few weeks of anxiously stalling to reach out and invite her to consider being my mentor, I realized how ridiculous I was being. For some reason I still felt a need to check in with her daughter Sophie, a recent coaching student of mine, and co-author of the Go To Help book.

I explained my idea and corresponding concerns (e.g.: I was being too needy, I’d look and sound pathetic, she wouldn’t have time, it would impact our friendship, etc.) to which she responded, “Are you kidding me?! You totally have to ask her!” We went on to laugh and talk about other things. Then I realized the real reason I called Sophie: I needed her to hold me accountable for making the ask.

We were all scheduled to have dinner the following week. I told myself that I’d ask her then. Fast forward to the dinner. I was at a bustling restaurant in downtown Durham with Deb, her husband Michael, Sophie, and my date, when the following rush of new fears flooded my mind: “even if I pull her aside it’s way too noisy in here; I don’t want to put her on the spot; she’ll need time to think; I still don’t know how to articulate what I’m asking for!”

As we wrapped up dinner I could see Sophie across the table saying to me with her eyes, “now’s your chance! ASK HER!” I smiled at her, and as I was awkwardly shimmying around the long circular booth to leave, I managed to say something like:

“So Deb, I have a question for you…but uh…, I think it makes more sense to email you about it.”

She responded, “Now I’m intrigued. I’ll keep a look out for it.”

After another couple of weeks passed, on a Thursday in mid-October, I FINALLY sat myself down and sent the email. Over the next few days I did everything in my power to not constantly stalk my inbox. When close to a week had gone by with no reply, I began to freak out a little. I even noted Deb’s activity on social media to seek logical reasons for why she hadn’t had a chance to write back…which was extremely unlike her.

The following Friday I got a call from Sophie on an unrelated topic and she asked if I’d sent the email. I cautiously conveyed to her the lack of response from her mom because I didn’t want to sound dramatic or make things awkward. She blurted out, “wait, something’s wrong. That’s not my mom. She would have responded immediately!” I agreed that it was strangely uncharacteristic. She insisted I resend the email.

And that’s when it hit me. The ultimate FACE-PLAM. I went into my sent folder to perform a second attempt, only to discover I sent it to the wrong person. I sent it to MYSELF!

I laughed out loud, swiftly sent a copy to Deb before any additional fear-based thoughts could stop me, and in less than two minutes she was calling my phone…

Me: Hiii therrre. (sheepishly)

Deb: “Firstly, YES! I’d be honored.

Second, do we need to talk to a therapist about you asking yourself to be your mentor?

Third, as your new mentor, you have got to write a LinkedIn article about this! That’s an order!”

And so here I am, following through on my accountability commitment to share this story with you all. What’s ironic is that one of the #goals I had for myself is getting back to my writing and being more actively engaged with networking. Two skills that Deb executes flawlessly in my opinion.

I’ve had so much fun composing this post and hope it serves as a reminder of the following:

  • That we ALL need help to succeed, and we are the ONLY ones who can ask for it.
  • Most people would jump at the chance to help someone out, I know I have.
  • Resistance manifests in so many ways…even comical ones!

So as we ease into 2023, I hope you’ll join me in:

  1. Taking ourselves less seriously.
  2. Getting more serious about connecting and re-connecting with each other in authentically vulnerable ways.
  3. Recognizing that our individual success is interdependent. i.e.: It’s okay to ask for and offer each other help, and it’s counter-strategic not to. And if you need even more convincing of this fact, or tips on how to seek support, check out Deb and Sophie’s book Go To Help.

I hope this article supports you in some small or big ways, and I encourage you to reach out to me if I can aid in your success. You can see more about me and my organizations by visiting and, or simply email me directly at Only genuine connections please.

Wishing you a healthy and prosperous 2023!