Coaching: 9 years in.

Jen Dary, the author of this article, coaches via laptop with an excited look.

In the beginning, I didn’t know I was coaching.

For the first 18 months of Plucky’s existence, I called it consulting — and some of it was. Employee Experience Audits, help with performance reviews, reviewing handbook policies. But my clients (especially the leaders among them) started to ask to have more individual conversations.

“Can I bounce something off you for an hour?”

“Can we talk once a month about the team’s direction?”

“It’s so helpful to air this out and have an outsider’s perspective.”

One day I realized that the verb underneath most of my Plucky work was coaching. This was back in 2014, back before folks hired coaches, before professional development funds meant more than conference tickets or a book to learn new skills. Claiming the title of coach — and selling that as a service — was strange and it took a while to fully embrace the identity. Everyone assumed that all coaches were life coaches; this wasn’t my interest. I like talking to people about work and how life shows up there, not the other way around.

So now I’m 9 years into coaching and instead of reflecting on the business this year, I’m going to reflect on the ways being a coach has changed me as a person. Because it has.

I’m still an extrovert but now I need lots of quiet.

It is undoubtedly still true that I get jazzed up while coaching, teaching and generally being around humans but this can quickly get out of balance. If my primary action is focused on listening to others, then I need times when someone is listening to me. In the past I’ve worked with a coach myself but I’m currently best balanced by old friendships, folks who knew me before I was a coach. These friendships come with natural balance; sometimes I’ll listen and sometimes I’ll talk and neither is weird.

I’m more direct.

In many conversations outside of work, I have to intentionally ask myself if I’m being asked to coach or if the person I’m hanging out with just wants to shoot the shit. I know what it’s like to be chatting with friends who are coaches, therapists or other supporting roles and it feels like you can’t just catch up without having A Problem.

This is frustrating for me as a person so I try extra hard to not steer personal conversations into deep topics if they’re not being invited. I often ask “do you want my opinion as a coach or as a wife/friend/sister/neighbor?” It’s direct and it helps.

My success metrics have evolved.

There’s a difference between empathetic listening and assumed distress. Coaches should not see themselves as saviors. No one wants to open up regularly to someone who will lean back in their fancy chair and tell you the answer to all of your problems. (Spoiler: that’s not possible.) But when learning to coach, it’s hard to feel like you mattered if the person ends their contract and they still have problems.

After 9 years in this gig, I can tell that my value is to be a soft landing, a savvy questioner, a connector to possibilities and a mirror to all of my client’s earned wisdom. People are so much wiser than they give themselves credit for. Success for me today means that I’ve held space for someone to process the topic at hand… and sometimes that’s game-changing. Sometimes not.

Jen Dary, author of the piece, holds up a Plucky product called Manager Weeklies.

Plucky is more than coaching.

It’s hard to find a model for Plucky at this point because it’s become such a reflection of my brain and my interests. I will always provide coaching as a service but only being a coach is too simple for me. I like flexing my creative muscles by inventing products, developing new courses and partnering with interesting people.

Over the years, that’s looked like: designing Mother’s Day performance reviews with the Kin team, a holiday video where my clients recorded themselves singing, facilitating at Bureau of Digital events, speaking to college students about their careers, holding monthly events for women to discuss their careers after Trump was elected, inventing a manager training program, organizing WorldWide 1:1s and coachathons when times were tough, and generally flying to random places to teach random things. Plus, all the products.

I don’t want to build a team.

When you’re doing something that’s working, everyone tells you to scale and I finally tried that a few years ago. I hired and trained very capable people whose jobs were in some way already related to coaching. I refocused Plucky’s marketing efforts on selling their time, held 1:1s and team meetings, worked to build culture with a team of people who had other full-time jobs. It was really hard and the most successful part about it was that some of these folks have gone on to continue their own coaching paths outside of Plucky.

Looking back, it was very important for me to say STOP. Business owners often let the market dictate what should happen next but forget about their own desires and level of fulfillment. I’m more energized by a smaller business that allows me to pivot quickly and decisively.


For the most part, I coach leaders or emerging leaders. I coach on Zoom or via phone and I take lots of notes using GoodNotes and an Apple Stylus. It’s very hard to get pictures of me working because coaching is private so all pictures have to be faked and that’s weird. (See: picture at the beginning of this piece!)

My business is almost exclusively word-of-mouth. Clients start with a bundle of sessions and then have the option of going monthly or grabbing another bundle. My clients are extremely interesting, self-aware and I learn a ton by working with them.

Coaching is an evolving identity and a constant reminder that you never know what’s going on for someone else. Social Media and social customs edit out the complex nuances of the people around us but I’ve found that the complex stories are really the ones that matter.

I’m grateful for all the clients I’ve worked with so far and all those to come. Thanks for 9 years of this work, world. Now, off to year 10!

Interested in working with Jen? Check out more information about Plucky coaching here.