Four Years of Plucky

To everyone who has ever supported Plucky,

Businesses, though they are believed to have been started in garages, basements and backyard sheds, are started over coffee. At least, that’s true about Plucky. I had an idea four years ago (a longer story for a longer day), but it was over coffees and lunches that I refined that idea and found a tiny door leading to space in the market.

Plucky turned 4 earlier this month and Plucky sure has grown. In the beginning, Plucky felt like a kid-sister business. I scrapped things together, asked for a lot of advice, watched how other grown-up businesses found their way. There’s still an element of that, but lately people have been asking me for advice about starting their own businesses. That’s how I know the tectonic plates of business have shifted underneath me.

I find it incredibly valuable to pause and reflect each year, though as a solo businessperson I don’t have any employees to gather in a conference room to hear a State of the Union. Then I realized something: YOU should hear the State of the Union. YOU- family and industry colleague and friend (and my dear third grade teacher!)- YOU should know how your retweets and shares, your coffees and your generous introductions have manifested Plucky’s growth this year.

So here we go!


I started tracking numbers this year. During Year 4, Plucky:

  • was open 3.5 days/week (thanks, Chris Dary, for the extra childcare!)
  • did work in countries
  • served 22 companies/clients
  • coached over 76 individuals
  • led audits and workshops (internal and external-facing) that have hosted 433 humans

Those last two numbers are very valuable to me because it means that, this year, more than 500 humans have told me their names, shared aspirational career growth and participated in content that empowers Adult Development. I care about this so much because I believe this is how I’ll change the world. Every employee who experiences a patient ear and the permission to find growth at work has the ability to bloom in new ways.

The ripples extend wide.

Behind the Scenes

While many of my hours have been spent working directly with clients this year, there is always significant work happening to expand the depth and path of the business. To that end, here are some new efforts that saw lift-off during Plucky’s 4th year:


The retreats, the 1:1s, the selling event tickets and the blog posts… it is all in service of healthy people making powerful, aligned contributions to their place of work. While I started firmly in tech, I am seeing growth in a number of other industries, like media, retail, insurance and religion (!). I love this because it means Plucky’s appeal is to humans.

Humans sure sounds like a powerful pipeline.

Year 5

A continued focus on supporting leadership services and speaking, here are a few efforts I have my eye on for Year 5:

  • Wider ReachSo Now You’re a Manager trainings in 2018 (possible cities include Philadelphia, Chicago, Portland and Austin)
  • Branding: Launch of Plucky Merch for sale, including 1:1 starter kit for new managers
  • Giving Back: free coaching for a different non-profit each quarter (focus on orgs that are minority-led or career-oriented)
  • Collaboration: obvious evolution for #PluckyWomen, perhaps folding it into an existing local effort


Thanks for the intros. Thanks for coming to #PluckyWomen. Thanks for showing up and growing during our coaching sessions. Thanks for reading my writing and believing in Plucky’s mission.

But thanks especially for being open to changing things in the workplace, world. Every moment you spend on self-aware actions moves the needle.

Change takes time. I have time. Here comes Year 5.

xo Jen

Want to keep up to date with humans at work and Plucky in general? Enter your info here to receive the monthly newsletter!

Announcing: So Now You’re A Manager

“The leadership is flagging.” This is the most common sentence I write in audits. You know why? (Get ready, it’s a shocker…)

Being a leader is REALLY EFFING TIRING.

Management can be such thrilling work. You are empowering humans to succeed! But it’s challenging work, it never ends and opportunities for training are few and far between. What does a successful day look like as a manager? What are the nuts and bolts of the job? And why the hell is your calendar booked solid with meetings?

I’m beyond pleased to announce a new Plucky workshop that trains and develops new managers. So Now You’re a Manager is a 2-day onsite training for those who embody the scaffolding to your company’s success. I’ve been thinking about this for over 3 years and it feels so good to have it ready for the wild!

This workshop, for managers and emerging managers, helps define what your role requires of you. We’ll address basic management skills and identify strategies for how to be successful. You’ll learn how to give feedback, how to earn trust and how to move things forward (which, at the end of the day, is one of the most important things you’ll do).

Are you flagging? Do you have flagging managers who need a refresh or who are hungry for the first official management training of their lives? Then get in touch and let’s shore up some of the most important roles at your org: the people peeps.

The Plucky Revolution.

Reflections on Year 2 of coaching, consulting and empowering humans in the workplace

Recently I had a long conversation with my Dad about how religious institutions and other community-based groups are hurting these days. He asked me where people find what they used to get out of church or scouts or local communities. I suggested that many find others on the internet, dating sites, social media sites, community sites like reddit, etc. But last night I thought more about community and the thing that all businesses I work with are concerned about: retention.

After running my beloved Plucky for the past two years, I’ve learned enough to suggest this: you will retain many more employees by building an internal community at your company that supports growth, vulnerability and healthy relationships. Period.

During Year 2, clients have hired me to coach leaders, hold office hours to support all employees, teach workshops at annual retreats or conduct performance reviews that dig deep. I’m a consistent presence that allows people to vent, let go of stress or feel empowered as they work through whatever’s on their plates. The humans I’ve encountered through this work often seem as though they’ve often been thirsty for support and community. I have adored quenching this as often as possible but now it’s time to name the elephant in the room: my own scalability.


I drove Plucky down lots of roads this past year. I onboarded many clients and I almost never said No because I wanted to help everyone and I knew I’d need to financially plan for a few months off when my son was born this summer.

Never saying No is awesome because of the amount of people I felt fortunate to affect and help. But never saying No is also psycho! Any wise business person will tell you this. There is immense power in defining why your business exists and spending every work hour possible working towards that goal.

So I’ve also started to get more specific about what the hell I’m doing.



I’ve written previously about inventing the term “Adult Development”, a concept that says that humans do not become perfect when they become adults. Adulthood, like childhood, is full of experiences that challenge us and teach us who we are. I believe that the highs and lows of our lives become the curriculum that we grow through. I also believe that it is in the very best interests of our companies to foster Employee Development, which, to me, is the future of Human Resources. Employee Development suggests that every person employed at a company is fallible and may require periods of additional support. A company with an Employee Development program embraces the fact that we are all people who will make mistakes and achieve victories. By working together, we can grow through these mistakes and victories… and ultimately we become stronger employees by being supported.

I champion this concept of Employee Development through our workplaces so that we help each other live the most fulfilling lives possible. But Employee Development also matters because it affects the very real problem of retention.

The technology industry has a ridiculous amount of jobs to offer qualified humans. I call the retention landscape in San Francisco and beyond the “18-month itch.” That’s about the amount of time new employees last before they start poking around their networks and having lunch at neighboring companies.

Do you know what the most compelling messaging is for your employees? We will help you evolve. We support you as you define and execute on the next phase of your career path and partner with you to leverage your talents for our business. We know you are a human who is learning tons outside of work and we believe that the lessons you learn at any hour of the day affects the work you do here. We value and empower Employee Development in our business.


I don’t suggest that Employee Development is an option to businesses; I assert that it is what will fundamentally put a business among the most successful on the planet. Embracing failure, giving credit for successes and providing support for people to be human builds strong relationships between a community of co-workers. This affects retention rates but also allows employees to be more efficient, effective and powerful workers because they work better through the inevitable distractions of conflict, burn-out and more. They highly appreciate the healthy community that they work for.

So this is what Year 3 will be about.


Over the next year I will develop curriculum for companies to build internal Employee Development programs. I plan to find speaking engagements that leverage my beliefs about these programs so that I can share my strategies and experiences with welcoming audiences.

And in addition to continuing some coaching, I am definitely going to continue running workshops, conducting audits and teaching at annual retreats. As a mega-extrovert, I adore spending time in rooms with humans. It refills my energy bucket and it makes my work feel alive.


Starting Year 3 I’m still a one-person shop. But given the fact that my family and my business have grown, I am skeptical that this will be true for long. Other than developing curriculum, I will likely add to Plucky’s team as well. It scares the hell out of me, but you know what? I recently gave birth to my second son. Labor is scary. But a few weeks after you had your kid you realize that you’re leading a whole family on the planet and the truth is that intimidating things help you grow, no matter how daunting they are.

So Plucky may grow its employee count this year too.


I’ll end this piece with one of my most compelling memories of Year 2. In March I was hired to teach workshops at a client’s annual retreat. I had some issues picking up the rental car and ended up bawling at the rental desk. I was 6 months pregnant, tired and (surely) a little extra emotional, so when I finally got in the car I wondered how the hell I was going to have the energy or focus to be an empowering force for this company over the next few days.

Then this cheesy pop song came on Rdio:

I might only have one match
But I can make an explosion
… Starting right now I’ll be strong
I’ll play my fight song
And I don’t really care if nobody else believes
‘Cause I’ve still got a lot of fight left in me

Suddenly I wasn’t bawling. Suddenly I was replaying this song and learning the lyrics and thinking “Yes, I am one match! But I can make an explosion!” I finished the drive and believed in myself again. It was bad-ass.

Bringing Adult Development to companies in the form of Employee Development programs feels like the explosion ready for me to make. And whether I’ve been tired because I’ve got a newborn or losing sleep because of work stress, I often replay this song for myself. (You should totally do that too, friends. Bookmark a song that gives you courage and an insane amount of strength. Then replay as-needed.) I’m a pretty tough cookie. And if there was ever a need for someone to empower an upcoming revolution, I’d volunteer myself. It inspires the hell out of me.

So let’s do this, Year 3. Let’s see how far Plucky’s beliefs and strategies can travel. Heads up; I’m not afraid to change the world.


Jen Dary

Founder, Be Plucky