What you’ll get from this post: a repeatable way to make a scary career move, coach a team through pressure, and show up when your tank is empty, built from one leader who has done all three more than once, plus five tasks you can start this week.
Jenny Olson’s grandma had a question for her. Why would you forsake a bird in the hand for two in the bush?
The bird in the hand was a successful, well-compensated career at Microsoft. The two in the bush was a short-term government job in a field Jenny had never worked in, for a fraction of the pay, with three small kids at home and college tuition on the horizon. She didn’t know if she’d be any good at it. She said yes anyway.
“The financial realities of that were scary as heck. I had built a lifestyle on a career that was well-compensated. I had three small kids. The golden handcuffs, what they say about walking away from golden handcuffs is epically true.”
Jenny Olson, Concordia College
That job was Recovery Reinvented, North Dakota’s initiative to eliminate the stigma of addiction. It changed how Jenny sees people. A few years later she said yes again, this time to VP of Advancement at Concordia College, a word she admits wasn’t anywhere on her bingo card.
I’ve known Jenny around the edges for years, and we finally sat down over burgers and then again on the podcast. The reason this conversation stuck with me is that almost everything she said about making a leap applies to a nonprofit director weighing a jump, a development officer staring down a capital campaign, or anybody who has ever talked themselves out of the thing they knew they should do. So this post is less about her resume and more about how she decides.
Jenny has taken a lot of risks, and when she looks back she sees a pattern she didn’t notice at the time. Every leap followed a person, not a title.
“I’ve always followed good leaders in my career. I fundamentally believe in the principle you are what you surround yourself and what you will become, and I always wanna learn from other people, and that fills my bucket, those relationships.”
Jenny Olson
The Recovery Reinvented move started that way. Mentors she’d looked up to at Microsoft, back when she was an intern in her early 20s, started raising their hands to go reinvent state government. Her read on it was simple. All the cool kids are over there, and I want to be part of that.
For a nonprofit leader this cuts two ways. First, it’s a filter for your own next move. Watch where the people you respect are spending their energy, and treat that as data. Second, it’s a reminder about who you work for and with. Jenny has no patience for working with anyone less than good people, and she means it as a career strategy, not a mood.
Here’s the part most people skip. Following a good leader isn’t passive, and it doesn’t happen on its own.
Jenny keeps tabs on the people she admires, sometimes for a decade, even when they’ve gone off to do something else entirely. She described nervously calling someone many years her senior, somebody she hadn’t seen in years, just to ask for coffee and keep the thread alive.
She also does something before she joins one of these people that’s worth stealing. She puts every card on the table. She tells them what she’s worried about, what she expects, and asks whether they’re on the same page, because she’d hate to walk into a relationship she valued and mess it up by accident.
If you want a mentor network that actually shows up when you need it, this is the mechanism. It’s a phone call once a year, the courage to make it, and total honesty when the real conversation comes.
I asked Jenny how she starts one of those all-cards-on-the-table conversations without overwhelming the other person. She laughed, because she’s not sure she’s ever done it without overwhelming somebody. Then she gave me the actual method.
She thinks it through ahead of time and rehearses it, sometimes a hundred times. She knows the three things she wants the other person to walk away having heard. And she opens by naming the shared goal out loud.
“We both want this thing to be successful and each other to be successful. Therefore, it’s in all of our best interests to have this super honest and transparent conversation, so I would like to start there and put my cards on the table.”
Jenny Olson
The reason she preps that hard is that the moment itself works against you. The conversation is awkward, the adrenaline is pumping, and your brain starts going. If you haven’t decided the three things in advance, they go out the window the second it gets tense.
This is a tool for board conversations, donor asks, and the talk with a staff member that you’ve been avoiding. Decide the outcome before you walk in. Name the shared goal first. Then say the hard thing.
Jenny runs a team of fundraisers now, and a lot of her coaching lands with women earlier in their careers who are wrestling with how much of themselves to bring to work. Her answer is grounded in one word: authenticity.
“For me, authenticity is at the core of everything, and it’s where I’m at my best and my most comfortable. What have I got to offer? My lived experience, what works for me, and being aware there are other ways to do things at the same time.”
Jenny Olson
She’s careful about how she frames advice. She tells people this is what works for me, it may or may not work for you. That line does a lot of quiet work. It offers real help without pretending her way is the only way.
I told her what I think happens to a lot of leaders. People who’ve had any kind of success tend to write it up as a playbook instead of a perspective. Jenny coaches the opposite. Here’s what I’d do, here’s why, and your mileage may vary because you’re a different person than I am.
“This is how you handle a tough donor meeting. Follow these five steps. It’s what got me here, so it’ll work for you.”
“Here’s how I handle a tough donor meeting, and here’s the thinking behind each move. It works for me because I process out loud and I feel things strongly. You might be wired differently. Take what’s useful and leave the rest.”
Same advice underneath. The second version gives your team permission to adapt it, which means they’ll actually use it instead of nodding and ignoring it. It also protects the relationship, because you’re not setting yourself up as the one right way.
For years Jenny dampened her personality down to fit the rooms she was in. Too much energy. Too loud. Too colorful. There’s no place for sequins at a table full of CFOs and CEOs. At some point, around the time of Recovery Reinvented, she’d proven enough to herself that she decided to test the premise.
The proof was small and it piled up. People would tell her, good for you, nobody’s ever interviewed that CEO with that many jokes and that much color, and we got more out of him because of it.
The clearest example was a gold sequined face mask she wore during COVID, on a trip to the White House with then-First Lady Kathryn Burgum to talk about Recovery Reinvented. She almost swapped it for a plain black one before going through Secret Service. Her leader waved her off.
“Sequins is your thing. The fact that she didn’t care. A tiny, tiny little thing, but seeing people and giving those little moments of affirmation is pretty liberating. So now I roll like that all the time without worrying about it.”
Jenny Olson
There’s a leadership lesson buried in a face mask. The affirmation that freed Jenny cost her leader nothing. If you run a team, you’re handing out or withholding those small permissions every day, usually without noticing. Give more of them.
Nonprofit leaders have to show up whether their energy is there or not. I asked Jenny how she does it when she’s running on empty, when she’d normally be at a 10 and she’s at a 2.
She has an internal switch for game time, the thing that makes you rise to the occasion when the moment calls for it. But her more useful answer was the backup plan for when the switch won’t flip.
She used to run half marathons, and she gave her friends the same advice every time. You get to mile 10 and you’re empty and miserable and stuck in your own head. That’s when you turn to the sidelines and start thanking the volunteers for coming out. They look at you like you’re crazy, because you’re the one running. And something happens.
“If you just figure out a way to push a little bit of it out, outward, it comes back, and then all of a sudden, somehow you magically feel better.”
Jenny Olson
I told her it’s the Go-Giver principle. If you need to get something, give more. For a leader whose job is lifting other people up, this is the one to internalize. On your worst day, find the person who needs you and pour into them. You’ll both come out ahead.
Jenny calls her path to Concordia baffling, and on the surface it is. Microsoft to a government addiction initiative, back to Microsoft to run the Fargo campus, then to higher education advancement, a field she’d literally told her friends she could never do.
But the themes are consistent, and they’re the ones she named earlier: good people, good leaders, mission-driven work. President Colin Irvine, who’d been bumping into her around the community, called with what she thought was a wild idea. She told him he was crazy and hung up. Then she didn’t sleep for two nights, called him back, and laid out every reason she wasn’t the right person. They went round and round for weeks.
Notice the move. She didn’t say yes on a gut rush. She listened to the nagging voice that said there’s something here, then she vetted it in depth across the community and the leadership team before she committed. Say yes to the people and the mission, but do your homework on whether the thing is what it’s cracked up to be.
The part of the conversation I keep thinking about is what Recovery Reinvented did to how Jenny sees people. She went from a global company moving at the speed of light to traveling North Dakota and meeting people she’d otherwise never have met.
“I had no idea all of these heroes were just working in my backyard, down in the trenches, day in and day out, slugging it out, changing the world from their tiny little corner of the state.”
Jenny Olson
She told me about one woman in recovery, happy and joyful and full of gratitude, who Jenny later learned carried an enormous amount of tragedy. Grown children who wouldn’t speak to her. Time served. A story Jenny isn’t sure she’d have survived. And there the woman was, changing the world with a joyful heart.
For a nonprofit leader, that’s the whole case for storytelling in one anecdote. The people doing the most good are often invisible, even to their neighbors, even to the person driving past them every day. Your job is to make them visible as the heroes they already are, not as objects of pity.
Our last question on every episode asks for one good thing to leave people with. Jenny’s came from a conversation she’d had that very week, about how many people are carrying more than anyone can see.
“I know how many people are silently walking around feeling like they’re failing at all of it. The reality is we all feel that, but it’s not true.”
Jenny Olson
She’s honest that she’s guilty of it herself. She tells her friends about the problem after she’s already solved it, and goes through the dark days alone, which she calls ridiculous. The fix is to say it out loud more often and lean into your people.
Everybody wants to help, so ask for more of it.
Find your people. Find your board of directors, the personal kind. Then actually use them. For a sector full of leaders who are quietly running on fumes and too proud to ask, this is the reminder worth taping to the monitor.
List the three leaders whose careers you’d follow right now. For each, write where they’re spending their energy. That list is a quiet map of your own next move.
Pick one mentor you’ve lost touch with and send the nervous message. Ask for coffee or a call. Rebuilding the thread is the whole point, and it takes courage, not cleverness.
Before it, write the three things you need the other person to hear and the shared goal you’ll open with. Rehearse the first two sentences out loud.
Catch yourself handing out a playbook. Rewrite one piece of standing advice you give your team as a perspective instead: here’s what works for me, here’s why, it may not be you.
List five people your organization serves who are heroes nobody sees. Pick one and plan how you’ll make them visible in your next newsletter or donor update.
If step five is the one you want help with, that’s the work we do at Tellwell. Start with the episode, then reach out.
There’s more in the episode than I could fit here, including the Talk framework for better conversations and why Jenny secretly loves a crisis. Give it a listen, and send it to someone who’s weighing a leap they don’t feel ready for.
If you want regular notes from me on storytelling and trust, sign up for Start with Story. And if you want to spend a couple of days with people who care about this work as much as you do, come to WellTold.
This episode is a good start. But if you’re ready to stop reading about storytelling and start investing in yours, let’s talk.
