By Nettie Owens, CPO-CD · The Sappari Group
Originally explored on Wake Up Women Leaders — Episode 8
You are in the middle of something hard. The plan hit a wall. The timeline shifted. The thing you counted on did not come through. And now you are standing in front of an obstacle — the kind of obstacles in leadership that do not care how prepared you were or how much you needed this to work.
What you do next is what defines you as a leader. What you do next when facing obstacles in leadership is what defines you as a leader.
That is not a motivational statement. It is a practical one. And it is the entire premise of Stoic philosophy — a school of thought that has been around for over 2,000 years, and that is as applicable to the woman leading a chamber of commerce or a nonprofit or a business in 2026 as it was to a Roman emperor in 161 AD.
In Episode 8 of Wake Up Women Leaders, Sensei Victoria Whitfield and I went straight into this topic — not as an abstract concept, but through the real stories of obstacles we have each faced, what we did with them, and what the research and philosophy behind this idea actually says about how leaders grow through obstacles in leadership.
Where This Idea Comes From
The phrase “the obstacle is the way” comes from a line written by Marcus Aurelius: what stands in the way becomes the way. Marcus Aurelius was not just any philosopher. He was a Roman emperor — one of the most powerful people in the world at the time — and he wrote those words in his personal journal, not for publication. He was working through his own leadership challenges in real time.
The concept was made accessible for modern readers by author Ryan Holiday in his book of the same name. Holiday is worth following — he has built an entire body of work around Stoic philosophy and how it applies to performance, leadership, and resilience.
One thing worth clarifying before we go further: Stoicism does not mean emotionless. That is a common misread. As I said during the episode:
“Dispel the idea that Stoicism means emotionless, because that’s not it at all. These are really just great ideas on how to live a good life — things like understanding that you are not the emotions that you feel, that you can pause before reacting.”
It is also not a religion, and it does not conflict with faith. You will find significant overlap between Stoic philosophy and many religious traditions. The core aim — what the Stoics called the summum bonum, the ultimate good — is to live a wise, courageous, just, and temperate life. That is not a narrow idea. It is a universal one, and it is especially relevant when navigating obstacles in leadership.
Why Women Leaders Need This Framework Now
When something goes wrong, the default reaction for most people is why is this happening to me? Victoria reframed that question in a way that is worth sitting with:
“Not, why is this happening to me — but why is this happening for me. Could it be that this is a resource being given to me? Is there a way I could see these lemons as the building blocks of a delicious lemonade I could make out of this situation?”
That shift — from victim of the obstacle to student of it — is not a mindset trick. It is a decision. And it is one that women leaders are particularly well-equipped to make, especially when facing obstacles in leadership.
Victoria brought in a concept from neuroscience that reframes how we understand our response to stress. Most people are familiar with the fight-or-flight response. Fewer people know about eustress — positive stress, the kind that sparks innovation rather than shutdown. And fewer still know that women, as a function of our stress response wiring, are designed to tend and befriend rather than fight or flee.
“When that happens, instead of being in fight, flight, or freeze as a central nervous response, we as women especially are designed to tend and befriend. We develop a relationship with the person, place, thing, issue, thought, feeling, to survive and thrive. And that obstacle, when we have a relationship with it, when we’re open to becoming curious — which is also a definitively feminine state — we can get creative.”
Curiosity. Creativity. Relationship. Those are not soft skills. They are survival skills — and they are exactly what obstacles in leadership are asking you to use.
The Sparring Partner Concept
One of the most useful frameworks from Stoic philosophy is the idea of the obstacle as a sparring partner. The point of a sparring partner is not to hurt you. It is to make you better. And a good sparring partner is always slightly better than you are — because that is the only way you actually improve.
Seeing obstacles in leadership as a sparring partner shifts your relationship with challenge.
I shared this from my own experience watching my daughters wrestle:
“The times that they would come home and say, I don’t want to wrestle that opponent because she’s really good — I’d say, thank goodness. You are so lucky you get to wrestle somebody who’s bigger and stronger than you are, because you will de facto become bigger and stronger by wrestling that person.”
That is the relationship you want to build with the challenges in your leadership. Not tolerance. Not endurance. Genuine engagement — because on the other side of that engagement are skills, strength, and confidence you cannot get any other way.
Which brings up a point that I asked our audience to write down during the episode:
“You don’t gain confidence by every day saying a mantra of, I wish I were more confident. You gain confidence by doing hard things and succeeding.”
That is not a reframe. That is a fact. Confidence is built through accumulated evidence — evidence that you faced the hard thing and moved through it. There is no shortcut, especially when working through obstacles in leadership.
Three Stories From the Room
Abstract concepts are useful. Real stories are more useful. Victoria and I both came to this episode with specific examples of obstacles that became the path forward — and they are worth sharing in full because they cover terrain that many leaders are navigating right now through obstacles in leadership.
Victoria: The window, the hospital, and the beginning of everything
Early in her career, Victoria was working at a non-profit, moving fast and refusing to ask for help, when a large stained-glass window — between 20 and 40 pounds — came down on her fingers. She ended up in the hospital.
“That working-myself-into-the-hospital experience was what forced me to rethink — what am I doing? Do I want to continue in this position or could this be an opportunity for me to re-evaluate my career?”
Victoria: The retreats that lost their home
Victoria had built a successful retreat business — five in-person multi-day events per year, both hosted at bed and breakfasts that people loved. During COVID, both properties sold. Her retreat homes were gone.
Her response: there is always a way around everything.
Nettie: The team that quit
In the spring of one of my best planning years — the year I was on cloud nine about the road ahead — I lost my entire professional organizing team. One by one, from January through May. The vision I had been building went up in smoke.
“We’re not saying that when these obstacles come up that you’re going to feel great about it.”
But alongside that grief, there was something else — a sense that this was happening for a reason.
What To Do When the Obstacle Shows Up
Knowing the philosophy is one thing. Having a practical approach when you are standing in front of an actual obstacles in leadership. Here is what Victoria and I landed on.
Name it and engage with it. Identify the obstacle clearly — write it down in one sentence. Then ask what skills, strength, or knowledge getting through this will require you to build. You are not just solving a problem. You are training for the next level.
Shift the question. Stop asking why is this happening to me and start asking why is this happening for me. That question opens up options that the first one closes down. Victoria put it simply: “How can I? Not, I can’t do this — how can I make this happen? That became the mindset shift.”
Find the just-for-today step. Victoria draws from the five Reiki principles, each of which begins with the phrase “just for today.” You do not have to solve the whole thing at once. Just for today — open the bill, look at the problem, ask one question, make one call. The boulder does not move in one push. It moves in small, consistent steps.
As I said to our audience directly: “Even if the obstacle is an enormous boulder in front of you, I promise you that there is a way to get to the other side. You’re not going to overcome this in one big leap. It’s going to be small, incremental steps.”
Allow the innovation. Victoria said this clearly, and it is worth sitting with: “As a woman leader, your decision to allow yourself to innovate, be curious and creative — that is what’s going to determine whether or not you are a strong leader and you’re growing, or you’re falling back and shrinking.”
The obstacle is not asking you to be fearless. It is asking you to be curious. Those are very different things, and the second one is actually available to you right now.
You Are Being Trained, Not Tested
The reframe that ties all of this together is simple. The obstacle is not a test of whether you deserve to be where you are going. It is training for the version of you that will be leading when you get there.
Every leader who has built something lasting has a version of the story Victoria and I told in this episode.
The question is not whether obstacles in leadership will show up. It will.
The question is what you do when it does — whether you ask why me, or whether you ask how can I.
Drop CONNECT in the comments if this is where you are right now. Victoria and I will reach out directly, and we will have a real conversation about what is in front of you and what the path forward looks like.
Watch the full Episode 8 conversation here
Next week we are talking about big vision on a tight budget — because that is one of the most common obstacles showing up for leaders right now, and it deserves a direct conversation. Join us Wednesday at 3:30pm ET.
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Nettie Owens, CPO-CD · The Sappari Group · sapparigroup.com · © 2026
