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

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Manager training: behind the music!

Every day I coach emerging leaders as they move into managerial roles and I hear the same themes in all of our conversations:
– How do I know if I’m doing well?
– I miss being in the weeds of the work.
– Humans are exhausting me.
– I hear about the problems but I don’t have the power to solve them.

These same themes come up in all verticals, from tech to healthcare to advertising to education to finance. Employees newly-promoted into manager roles are all wondering the same thing: was this the right move? Why does it feel so… hard?

Sometimes you get more money if you’re managing. But the money doesn’t help when you’re about to go into your 14th meeting of the day, unable to complete the work decided on in meetings because your schedule is full of, well, other meetings. The money doesn’t help when you stress about translating difficult messages from more senior leadership to your own reports.

And the money doesn’t help when you burn out tragically fast, quit and go freelance.

So there has to be a more compelling reason to become a manager and I feel authentic when I say this: managing is one of the most important opportunities you may have. Ever.

Managers lead other humans, assembling and motivating them to work together towards a common goal. Leading humans is a killer skill to have, especially if you do not use it for evil!

For this reason, I recently launched So Now You’re a Manager, a 2-day mini-conf for people who have less than 5 years experience as a manager! Let’s make some great future leaders, shall we?

The first one happened in Brooklyn, NY. The second one is happening in a few weeks in San Francisco. If any of this post resonates with you, you should totally come. And if your boss needs convincing to approve budget or time off, you can send them this post so they know what to expect:

Leadership Mission Statements
If you have never considered yourself a leader before, you are going to have an inefficient time leading. Who are you as a leader? What values do you believe in? How will your reports see you and what will they lean on you for? SNYAM attendees defined their leadership values, style and the skills they wanted to focus on for the next 6 months.

You could see attendees come alive in Brooklyn as they read their statements aloud. This also proved that all of the humans in the room were not the same! Some spoke of transparency, others of diversity and others of kindness. It was fantastic to see attendees grow self-aware about their own career paths.

Team as Product
If you’re building a product, you face many decisions about adding features, clarifying priorities and holding a vision for it so all can see. What if you thought of your team as a product? How would you hire differently if you knew you had a bunch of quiet people already on the team? What skills and personality traits would help the team be more successful?

SNYAM attendees were asked to design their current teams with play dough… and then explain their designs to the group they were sitting with. Sitting among peers who understand managing UP and corralling independent team members was so useful; they made smart observations about each others’ teams and many future decisions became obvious along the way.

1:1 practice
Why are 1:1s helpful? How often should you have them? What do you do if the person sitting across from you is a cold, stone wall of emotion and is acting like a robot? (Yeah. That’s the real talk right there.)

After covering some basics, attendees paired up and took 45 minutes to practice 1:1s with each other. From a variety of industries, they came back together to share that they felt helped and like helpers, that there were many similarities in their problems and victories! Getting an outside perspective from another person was refreshing, whether they did a walking 1:1, found a bench outside to sit on or made their way to a coffee shop. (Changing venues for 1:1s was a good experiment, too!)

Blame Jen!
Maybe you’re new to management and you know you need to evolve your identity (especially if you’ll be managing people who used to be peers!), but it seems cheesy and lame to start doing trust falls, SNYAM gives you the superpower of BLAMING JEN!

Attendees were given folders of manager tools, including work wheels, career planning guides, job description guidance and team dynamic activities. When they got back to work and wanted to try something new, they could always blame SNYAM (or Jen!) to build momentum around the new tool! Identity issues resolved.

If you are taking time and budget to be somewhere for 2 days, you better get something out of it. Attendees got Take-away Breaks twice a day so they could keep notes about what they and their specific teams need.

Coaching call 6 weeks later
Let’s be real; these attendees were out of the office for two days and then returned back to mega-emails, meetings and the grind. They brought instincts back with them and a new energy, but change has better odds when it’s monitored.

Six weeks after SNYAM, attendees booked 30 minute coaching calls with me to check in on how things were going. Sometimes they asked questions about their specific teams, sometimes they vented and sometimes we problem-solved together. Either way, it was a strong finish to the experience and compelling to see the ways they were integrating what they learned into daily managerial life.

If you’re a new manager (or an experienced manager who needs a new take), please join us in a few weeks. Tickets are limited to 20 attendees and we would love to see you there.

Because this conference will change things for you. It will give you a break in your schedule, a much-needed 2 day breather from the normal grind and it will allow you to consider, intentionally, who you are and what you’re leading. Successful careers and companies are built by the strong leaders who serve them; investing in yourself will give you the best shot at doing just that.

Companies who have sent their leaders to SNYAM in the past: Citi Bike, ExpandTheRoom, Fastspot, Four Kitchens, Glossier, SkyHi, The New York Times, VTS, Yellow Pencil, ZeroCater… and more!