June 19, 2026The Mindset Shift That Helps You Keep Going

There is a particular kind of humbling that comes from being bad at something in front of other people, especially when you expected to be at least decent. Most of us know that feeling, and most of us know what we do next: we quietly stop showing up. We tell ourselves we will “get back to it eventually.” We never do. What separates the people who push through that moment from the people who walk away is not talent, and it is not luck. It is a mindset.

Specifically, it is a mindset about what to do in the seconds right after you mess up, and whether you have a plan for that moment or you are simply hoping it does not happen again.

That is the territory keynote speaker Sheri Jacobs and I explored in a recent conversation that started, of all places, on a tennis court. Sheri is the bestselling author of The Unexpected Power of Boundaries, an innovation strategist who has surveyed more than half a million people, and someone who has spent years studying how leaders and organizations respond to risk, change, and uncertainty.

But in this conversation, she was not talking about boardrooms. She was talking about picking up a racket later in life, discovering she was genuinely bad at the sport, and almost quitting before she had really started. What she learned on the court turned out to be a near-perfect blueprint for the mindset that determines whether people grow or give up, whether on a tennis court, in a leadership role, or anywhere progress requires getting comfortable with being bad before you get good.

🎥 Watch and listen to the full interview about creativity, resilience and mindset here

Why Starting Late Is Better Than Never

There is a quiet narrative many of us carry that the right time to try something new has already passed. We see people who started young, who have a decade of practice behind them, and we assume the gap is too wide to close.

Sheri’s experience with tennis pushes back against that story in a way that I found genuinely useful, not just as encouragement, but as a mindset reframe. She did not pick up the sport as a child. She came to it later, as an adult, already accomplished in other areas of her life, and was met with the uncomfortable reality that competence in one domain does not transfer to another. Being a successful author, researcher, and CEO did not make the ball go where she wanted it to go.

What struck me most about this part of the conversation is how universal that experience is, even though we rarely talk about it directly.

Most adults avoid starting new things specifically because they have gotten used to being good at things. The mindset of a beginner, the willingness to be visibly, awkwardly bad at something in front of others, becomes harder to access the more expertise we accumulate elsewhere. Sheri’s choice to start tennis anyway, and to keep going even after discovering how hard it was, is not really a story about athleticism.

It is a story about a mindset that treats “starting late” as a logistical fact rather than a disqualifying one. The clock does not determine whether you are allowed to begin. Your mindset does.

The Moment Everyone Wants to Quit

Every person who has ever tried to learn something difficult has hit this moment: the point where the gap between what you expected and what is actually happening becomes too obvious to ignore. For Sheri, that moment came early in her tennis journey, when she realized she was not just inexperienced, she was bad, and the difference between those two things matters. Inexperience implies you are on a trajectory. Being bad, in the moment, feels like evidence that maybe you should not be doing this at all.

This is the exact junction where mindset either saves you or sinks you. Most people, when they hit this wall, do not consciously decide to quit. They simply stop scheduling the next session. They find reasons to be busy. They tell themselves they will “pick it back up” at some vague future point that never arrives.

I have watched this happen with leaders trying to develop a new skill, with teams trying to adopt a new process, and with organizations trying to shift their culture. The discomfort of being visibly bad at something new triggers a quiet retreat, and the retreat gets rationalized as something other than quitting. The mindset shift Sheri describes is not about eliminating that discomfort. It is about recognizing it for what it is, a normal and predictable part of the process, rather than a signal that you have made a mistake by starting.

The Pause and Reset Practice That Changed Everything

Here is where the conversation moved from relatable to genuinely useful. Sheri described a specific practice she developed: after two or three bad shots in a row, she pauses. She does not immediately try again with the same approach, hoping that this time it will somehow work. She stops, steps back, and resets before continuing.

What I love about this is how unglamorous it is. There is no dramatic turning point, no breakthrough moment of clarity. It is a small, repeatable habit, and that is precisely why it works. The mindset Sheri describes is one that catches the pattern of repeated failure before it becomes a spiral. Most of us, when we are frustrated, do the opposite. We speed up. We hit the ball harder, send the email faster, push the same argument louder, as if intensity could substitute for adjustment. The pause is a mindset interrupt. It creates a small gap between the mistake and the next attempt, and that gap is where actual learning happens.

I have seen this exact dynamic play out in professional settings more times than I can count. A team keeps running the same kind of meeting that does not produce decisions, and instead of pausing to ask why, they simply schedule another one, hoping that this time it will be different. A leader keeps delivering the same kind of feedback that does not change behavior, and instead of stepping back, they repeat it, louder, more often. The mindset that Sheri brought to the tennis court, pause after the pattern repeats, do not just repeat the pattern, is exactly the mindset that separates teams that improve from teams that stay stuck doing the same thing and expecting a different outcome.

You Do Not Need a Full Strategy Overhaul

One of the most quietly radical parts of this conversation was Sheri’s insistence that the answer to a bad pattern is rarely a complete overhaul. After the pause, she does not rebuild her entire approach to the game. She changes one small thing. That is it. One adjustment was tested, observed, and then either kept or replaced with another small adjustment.

This matters because the mindset most of us default to when something is not working is the opposite. We assume that if the small version of our approach is failing, the solution must be a bigger, more dramatic version of change. New system. New strategy. New everything. And because that level of change feels exhausting and risky, we often do not change anything at all. The mindset of incremental adjustment offers a third option that is far more sustainable: you do not have to choose between staying exactly the same and blowing everything up. You can change one variable, see what happens, and let that information guide the next small change.

I think this is one of the most transferable lessons in the entire conversation, because it applies almost identically to leadership and to organizational change. A mindset built around incremental adjustment is a mindset that treats improvement as a series of small experiments rather than a single high-stakes bet. It is less dramatic, which is exactly why it works. Dramatic changes are hard to sustain and easy to abandon. Small adjustments, made consistently, compound into something significant, and they do it without requiring the kind of all-or-nothing commitment that so often leads to paralysis.

Letting Go of the Need to Win on the First Shot

There is a phrase from this conversation that has stayed with me since I first heard it: the idea that you do not need to win the point on the first shot. In tennis, that means getting the ball in play, keeping the rally going, and building toward a winning position rather than trying to end the point with one perfect, high-risk hit. In almost every other context, it means something just as important: progress does not require an immediate, decisive victory.

The mindset that demands an immediate win on the first attempt is, in my experience, one of the most quietly destructive mindsets in professional life. It shows up when someone refuses to send a draft until it is perfect, when a team will not launch a pilot until every possible risk has been eliminated, and when a leader hesitates to have a difficult conversation until they have scripted the exact right words. In each case, the underlying belief is the same: if the first move is not the winning move, it was a failure.

What Sheri’s framing offers instead is a mindset built around sequence rather than single moments. Getting the ball in play is not the consolation prize. It is the strategy. The point is won through the rally, through the accumulation of small, sound decisions that keep you in position to capitalize when the opportunity arrives. I think this reframing alone could change how a lot of people approach their work, because it removes the impossible standard of getting everything right immediately and replaces it with a much more achievable standard: stay in the rally, keep making sound moves, and trust that the opening will come.

How Mistakes Become Your Best Teacher

The final piece of this conversation is also the hardest one to feel in the moment, even though it is the easiest one to say afterward. Sheri put it simply: it is easier, after the fact, to look back and recognize that the mistakes were what made you better. In the moment, it does not feel that way at all. In the moment, a mistake feels like evidence that you are failing, not like evidence that you are learning.

This gap between how mistakes feel in real time and how they look in retrospect is, I think, one of the central challenges of building a resilient mindset. We are not wired to experience a mistake as useful information while it is happening. We experience it as a threat, an embarrassment, a setback. The mindset shift Sheri describes is not about changing that initial reaction, because that reaction is largely involuntary. It is about trusting, even while the reaction is happening, that this moment will eventually be reclassified. The bad shot that frustrated you today is very likely the shot that, six months from now, you will point to as the one that taught you the adjustment you needed.

I have started thinking about this as a kind of mindset patience, a willingness to withhold judgment about a mistake until enough time has passed to see what it actually produced. It does not make the mistake feel good in the moment. But it does change what you do next. Instead of treating the mistake as proof that you should stop, you treat it as data that has not finished being processed yet.

From the Court to the Boardroom

It would be easy to read all of this as a nice metaphor about tennis that happens to apply loosely to work. But the more I sat with this conversation, the more I realized the connection runs much deeper than metaphor. The mindset Sheri describes, pause after repeated mistakes, make small adjustments instead of overhauls, let go of needing an immediate win, and trust that mistakes will eventually prove useful, is not an analogy for how teams and leaders operate. It is a description of how the best ones actually do operate.

Think about how often organizational change fails, not because the strategy was wrong, but because the mindset around execution was wrong. Leaders launch a new initiative, it does not produce immediate results, and instead of pausing to make a small adjustment, the whole initiative gets scrapped and replaced with a different big idea, which then suffers the same fate. The mindset of demanding a win on the first shot, applied at an organizational scale, produces a cycle of launches and abandonments that never gives any single approach enough time to actually work.

The teams and leaders who break that cycle are the ones who bring a different mindset to the table from the start. They expect the first version of anything to be rough. They build in pauses, often disguised as retrospectives or check-ins, specifically so that patterns of repeated failure get caught early. And critically, they resist the urge to throw out everything and start over when something does not work immediately. They look for the one small adjustment that might change the trajectory, test it, and keep iterating. This is the same mindset Sheri brought to the tennis court, just applied at a different scale.

Building a Culture Where This Mindset Can Thrive

One of the things I appreciate most about Sheri’s broader body of work, particularly the ideas explored in The Unexpected Power of Boundaries, is that she does not treat this mindset as something individuals have to muscle through entirely on their own. Mindset is shaped by environment. A person can have every intention of pausing, adjusting, and staying in the rally, but if the environment around them punishes any visible mistake, that mindset becomes nearly impossible to sustain.

This is where leadership has real influence. A team’s collective mindset around mistakes is set, largely, by how leaders respond when mistakes happen. If the response is blame, or if there is an unspoken expectation that everything should work the first time perfectly, people will quietly adopt a mindset of risk avoidance, even if no one ever says that explicitly. They will stop proposing the small adjustment, because proposing it means admitting the first version was not right, and that feels dangerous.

On the other hand, when leaders model the exact behavior Sheri describes, pausing publicly to acknowledge a pattern is not working, making a visible small adjustment rather than a dramatic reversal, and talking openly about what a recent mistake taught them, that mindset becomes contagious. People do not need to be told to take smart risks. They watch what happens when someone else takes one, and they calibrate their own mindset accordingly. This connects directly to themes Sheri explores around innovation and creativity, where the conditions that allow new ideas to emerge are rarely about removing all risk. They are about creating a shared mindset where smart, small risks are expected and supported.

Why This Mindset Matters Beyond the Obvious

It would be reasonable to assume this conversation is primarily about resilience, and on the surface, it is. But the more I reflect on it, the more I think the deeper subject is actually about sustainability. A mindset built around dramatic wins and dramatic failures is exhausting to maintain, both for individuals and for organizations. It requires constant high stakes, constant emotional swings, and it leaves very little room for the slow, unglamorous work of getting better at something over time.

The mindset Sheri describes is, by contrast, sustainable precisely because it is small. Pausing after a few bad shots does not require a crisis. Making one small adjustment does not require a strategic offsite. Letting go of the need to win immediately does not require lowering your standards; it requires redefining what progress looks like at any given moment. And recognizing that mistakes will eventually prove useful does not require you to enjoy making them; it just requires you to keep going long enough to find out what they taught you.

This is, I think, the real reason this particular mindset helps people stop quitting. It is not because it makes failure feel good. It is because it makes the process of improvement feel manageable, repeatable, and survivable, week after week, in a way that bigger, high-stakes attempts at transformation rarely do. Sheri’s experience on the tennis court is a small, almost mundane example, and that is exactly its power.

The mindset that got her through a frustrating start on the court is the same mindset that, applied consistently, gets people through frustrating starts in their careers, their leadership roles, and their organizations.

A Mindset Worth Carrying Forward

If there is one idea from this conversation I keep returning to, it is this: the mindset that helps you stop quitting is not about loving the moments when things go wrong. It is about having a plan for what to do immediately afterward, so that those moments do not compound into a pattern, and that pattern does not compound into giving up entirely. Pause, adjust, let go of the need for an immediate win, and trust that the mistakes will eventually make sense.

I think about how many things people have quietly stopped doing, not because they were truly bad at them, but because they never developed this mindset around the early, frustrating stage of being bad at something new. Sheri’s story is a reminder that the gap between quitting and continuing is often much smaller than it feels in the moment, and that the right mindset can close that gap without requiring heroic effort. It just requires a pause, a small adjustment, and a willingness to keep playing the next point.

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🎥 Watch the full interview here