http://www.ajackedexperience.com/

A Jacked Experience, Toronto, ON (2026)

09/22/2026

I can't stop noticing this lately.

It's coming up almost daily, in my coaching conversations and in my personal life.

A parent talking about their child.
Someone talking about their spouse.
A leader talking about their team.

And I keep hearing some version of:

They should know.

They should know what's expected of them.

They should know they're doing a good job.

They should know I want to hear what they think.

They should know it's okay to disagree.

They should know they can come to me.

But I'm not sure they do.

I think there is an Explicitness Gap here.

We assume we've been clear. Or because we said something once, the other person knows we still mean it.

But the longer the time between hearing “I want you to speak up” and actually having the opportunity to speak up, the more room there is for our internal dialogue to get in the way.

Maybe they didn't really mean it.
Maybe this isn't the right time.
Maybe I just won't say anything.

And here's the part I think we miss:

People test the waters.

A child shares something small before sharing the big thing.

An employee offers an opinion a little tentatively.

Someone asks a question they're not entirely sure they should ask.

It might look insignificant to us.

To them, it might be a test:

Did you really mean what you said?

How we respond gives them information.

If the small attempt is noticed and welcomed, maybe they take a bigger step next time.

If it goes unnoticed, that tells them something too.

This isn't about needing constant reassurance.

It's about how often we expect people to act confidently on things we've left them to assume.

Say the thing.

Tell them you're proud of them.
Tell them why you trust them.
Ask for their opinion.
Be clear about what you expect.

And when they test the waters, notice.

What are you assuming someone already knows that might be worth saying out loud today?

09/14/2026

“I want to be more intentional about what comes next.”

I've heard some version of this several times recently from people reaching out to work with me.

And what's interesting is that these aren't people who are stuck.

They're successful. Capable. Respected.

They have options.

Maybe that's part of what makes it hard.

Earlier in our careers, the path can feel a little more obvious.

Get the experience.
Earn the promotion.
Take on more responsibility.
Build credibility.

But eventually, you can reach a point where there isn't an obvious next step.

You've earned more autonomy. More influence. More choice.

And the question changes.

It's no longer:

What could I do next?

There are probably plenty of answers to that.

The harder question becomes:

What do I actually want to build from here?

I think there's a gap between having options and having direction.

And more options don't necessarily close it.

Sometimes they make it wider.

Because being capable of doing something isn't the same as intentionally choosing it.

A bigger role.
A different role.
A company.
A team.
A different way of leading.
Even a different definition of success.

At some point, growth becomes less about following the opportunities in front of you and more about deciding which ones belong in the future you're trying to create.

Maybe that's the Direction Gap.

If no one else was defining what success should look like from here, what would you choose?

09/08/2026

The Self-Trust Gap

You can be highly capable and still find yourself looking for someone to tell you:

“Yes. That’s the right decision.”

Especially when the stakes get higher.

So you gather more information.

Ask more people.

Have another conversation.

Keep the options open a little longer.

Wait for one more sign that you’re making the right call.

It can look like thoughtful decision-making.

Sometimes it is.

But sometimes?

We just don’t trust ourselves enough to decide yet.

The further you move into leadership, the less certainty you’re likely to have before you need to act.

Eventually, there may be no one above you who can give you the answer.

You have to make the call.

Not because you know everything.

Because you know enough to make a thoughtful decision and trust yourself with what happens next.

That’s the difference I’ve been thinking about between confidence and self-trust.

Confidence says:

“I know this will work.”

Self-trust says:

“I trust myself to navigate what happens next.”

That distinction matters.

Because constantly looking for certainty can keep really capable people stuck.

Overthinking.

Over-consulting.

Delaying decisions.

Looking outside themselves for reassurance they may never get.

Self-trust isn’t believing you’ll always get it right.

It’s knowing you can make the decision, learn from what happens, and adjust when you need to.

So maybe the question isn’t:

“How do I know this is the right decision?”

Maybe it’s:

“What would I decide if I trusted myself to handle whatever comes next?”

09/01/2026

**The Freedom Gap**

We spend years wanting more autonomy.

More authority.
More influence.
More say in the decisions.

And then one day, you get it.

And realize:

**Nobody is coming to tell you what to do.**

No one is setting the priorities.

No one is giving you the answer.

No one is above you to approve the direction.

The decisions are yours.

It sounds like freedom.

Sometimes it feels more like standing in an empty room thinking:

**Where do I even begin?**

I've seen this happen when someone steps into a much bigger leadership role, becomes the senior-most leader, or takes ownership of a company.

When someone else was ultimately accountable, there was a reference point.

You might not have agreed with it.

You might have wished for more freedom.

But you knew what you were responding to.

Now you have to decide what you're actually moving toward.

And this is where some leaders get stuck.

They freeze because there are too many choices.

Or they get incredibly busy.

New initiatives.
More meetings.
More problem-solving.
More decisions.

They're moving constantly, but haven't stopped long enough to ask:

**Are we actually moving in the right direction?**

Because autonomy gives you freedom of choice.

**It doesn't tell you what to choose.**

That's where another leadership muscle becomes important:

**Self-trust.**

The ability to pause.

Get clear on what matters.

Make a decision without needing someone else to validate it.

Choose a direction before you have every answer.

Maybe that's why the word **intentional** keeps coming up in so many of my coaching conversations.

People aren't just asking, “How do I become more successful?”

They're asking:

**“How do I become more intentional about what comes next?”**

And that's harder when nobody else is defining the destination.

Because eventually, you have to ask:

**What do I actually want?**

And:

**Do I trust myself enough to choose it?**

More freedom doesn't always make leadership easier.

Sometimes it simply reveals a different gap:

**Learning to lead yourself when there is no one left to lead you.**

08/25/2026

LEADERSHIP GAP: We’re experiencing a lot. But are we learning from it?

I was out cycling today and realized how much of my thinking happens when I’m doing something physical.

Walking the dog.
Lifting weights.
Cycling.
Getting outside.

It gives my brain space to process.

It made me think about a conversation I had with a client recently.

At the end of our session, I asked:

“What was most helpful for you today?”

Their answer?

“The realization that I need to take more time to reflect.”

Not more information.

Not another strategy.

Reflection.

And I think this is a bigger leadership gap than we talk about.

We experience SO much as leaders.

Difficult conversations.
Missed expectations.
Conflict.
Feedback.
Wins.
Decisions that didn’t go as planned.

But how often do we actually stop and ask:

What just happened here?

What was my role in it?

What did I assume?

What did I avoid?

What did I notice?

What might I do differently next time?

What did I learn about myself?

Because here’s the thing:

Experience alone doesn’t necessarily make us better leaders.

Processed experience does.

And I think this is especially important for newer leaders who may not yet have developed the habit of stepping outside the situation and observing themselves in it.

But experienced leaders can fall into the same trap.

We have so much experience that we can become very quick to interpret.

“I’ve seen this before.”

“I know what’s happening.”

“They just need…”

And sometimes experience becomes a shortcut around curiosity and reflection.

The irony?

The busier and more senior we become, the more important reflection becomes.

Our teams need answers.

Our organizations need decisions.

There’s always another meeting.

Another deadline.

Another problem to solve.

So who is asking the leader the questions?

“What are you noticing about yourself?”

“What might you be missing?”

“What is this situation teaching you?”

Because without reflection, we can spend years accumulating experience without necessarily evolving from it.

Sometimes stepping away from the doing is where the real learning happens.

Where do you do your best thinking?

08/18/2026

I was working with a senior executive today who wanted to inspire their team to take more ownership.

More accountability for their performance.

More commitment to the collective outcome.

More of that feeling of we're in this together.

We talked about incentives. Accountability. Goals. Team structure.

And then we kept coming back to something much simpler:

How well do you actually know these people?

Not their roles.

Not their strengths.

Not what you've observed about them over the years.

Them.

What matters to them right now?

What motivates them?

What's getting in the way?

What are they seeing that you aren't?

What would make the bigger picture matter more to them?

It got me thinking about a leadership gap I see often, particularly as people become more senior.

Curiosity.

We build our careers on knowing.

Knowing the business.
Knowing the answer.
Knowing what good looks like.
Knowing our people.

And eventually, we can become so used to knowing that we stop asking.

We start filling in the blanks with assumptions.

But knowing someone isn't the same as understanding them.

And the more senior you become, the less you can rely on your ability to know and the more you need to rely on your ability to understand.

People don't necessarily need another motivational speech.

Sometimes they need to feel seen.

Heard.

Understood.

And when people feel understood, something shifts.

They're more willing to understand.

To engage.

To take ownership.

To contribute.

Not because you figured out how to motivate them.

Because you took the time to know them.

Maybe inspiration isn't something you give people.

Maybe it's something that happens when people feel genuinely connected to the person, the purpose, and the work.

Worth thinking about.

08/12/2026

**The Leadership Gap: When your definition of success no longer fits.**

Three executives have come to me recently with essentially the same goal:

*Help me figure out how to leave.*

Different organizations. Different circumstances. Different careers.

But all three had reached a point where something wasn’t working anymore.

At first, leaving seemed like the answer.

But once we slowed down and started exploring what was actually underneath the dissatisfaction, something interesting happened.

In each case, it became apparent that leaving wasn’t necessarily what they wanted or needed to do.

They needed to recalibrate.

The definition of success they had been operating under no longer quite fit who they were or what mattered to them now.

And this can happen to any of us, at any point, in any role.

Our priorities shift with the seasons of our lives.

What motivated us five years ago may not motivate us today.

The next title may not feel as exciting.

More responsibility may not feel like the obvious answer.

And what once looked like ambition can start to feel like obligation.

Sometimes we mistake that feeling for a sign that we need a new job.

Sometimes we do.

But sometimes the more important question is:

**What if the problem isn’t the job? What if your definition of success is outdated?**

The definition that got you here was built at a different point in your life and career.

It made sense then.

It may not make sense now.

So before making a major career decision, get curious.

What does success actually mean to you today?

What do you want more of?

What are you no longer willing to trade for achievement?

What matters now that didn’t matter five or ten years ago?

And what would it look like to approach your current role through that new definition?

Sometimes that clarity changes your relationship with the work you’re already doing.

And sometimes it confirms that it’s time to move on.

Either way, you’re making the decision from clarity rather than frustration.

Because growth doesn’t always mean finding the next thing.

Sometimes it means redefining what meaningful, fulfilling and successful look like at the level you’re at now.

08/05/2026

Leadership Gap #5: The Evidence Gap

One of the biggest mistakes I see leaders make isn't choosing the wrong leadership approach.

It's abandoning the right one too soon.

I recently worked with a senior executive who had relocated internationally into a new organization, a new culture and a very different way of working.

As the pressure mounted, she began questioning everything.

Instead of leading the way she always had, she felt she needed to become a completely different leader to succeed.

It's a trap many of us fall into.

When we're uncomfortable, our minds become incredibly good at creating stories:

"Maybe I'm not being direct enough."

"Maybe I need to be more involved."

"Maybe I need to push harder."

"Maybe this leadership style just doesn't work here."

The challenge is that leadership isn't an experiment you can evaluate after one conversation or one week.

Trust takes time.

Ownership takes time.

Confidence takes time.

People need consistency before they believe your leadership is genuine.

Together, we worked on something that sounds simple, but is often incredibly difficult: staying aligned with the leader she had already worked so hard to become.

Rather than abandoning her values, she committed to leading with them consistently.

Slowly, things began to shift.

Her team took greater ownership.

People became more accountable for their work and their development.

She stopped feeling like she needed to hold everyone's hand, freeing herself from the burnout that had been quietly building.

Most importantly, she finally had the space to focus on the strategic leadership her organization needed from her.

Here's what struck me most.

Nothing changed overnight.

What changed was that she stayed with the right behaviours long enough to gather the evidence that they were working.

That's the Leadership Gap.

Too many leaders change direction before they've given the right approach enough time to produce results.

They flip-flop between leadership styles, priorities and expectations.

The result?

Teams become confused.

Trust weakens.

Relationships become inconsistent.

And leaders mistakenly conclude that the approach didn't work.

Often, it wasn't the approach.

It was the lack of consistency.

Leadership isn't about chasing the next technique.

It's about having the patience and discipline to stay aligned with your values long enough for your people to experience consistency—and for you to experience the results.

Sometimes the greatest value of coaching isn't introducing a new way to lead.

It's helping leaders stay the course long enough to discover they were on the right path all along.

Where have you seen The Evidence Gap show up—in yourself or in leaders you've worked with?

07/30/2026

Bridging the Leadership Gap #4: When Being Involved Feels Like Leadership

One of the hardest transitions leaders face is recognizing that the work that made them successful is not always the work that will make them successful at the next level.

This week, I was coaching a leader who felt strongly that they needed to be involved in almost everything their team was working on.

Not because they didn't trust their people.

Not because their team wasn't capable.

But because they believed being close to every conversation was the best way to stay informed.

Their concern was valid:

"If I'm not in those meetings, how will I know what's happening when senior leaders ask questions?"

It sounds responsible.

And yet, it uncovered a leadership gap I see often.

We can confuse being involved with being effective.

Many leaders unintentionally create a false sense of control by staying connected to every detail, every decision, and every conversation.

The challenge is that the more time we spend inside work our teams are capable of owning, the less time we have available for the work only leaders can do.

Creating vision.

Thinking strategically.

Building relationships.

Developing people.

Removing obstacles.

Preparing the organization for what is ahead.

And this is often where leaders find themselves stuck.

They want more time to lead, but they are still holding onto responsibilities that no longer belong at their level.

The question I often ask is:

What are you holding onto that is preventing you from leading at the level your role now requires?

This isn't simply a delegation issue.

It's an identity shift.

Many leaders are promoted because they are exceptional at getting things done.

They solve problems.

They have expertise.

They are dependable.

Those qualities matter.

But leadership requires a new definition of value.

It moves from:

"How much can I accomplish?"

to:

"How much can I enable others to accomplish?"

The strongest leaders don't become the centre of every decision.

They create clarity instead of dependency.

They build trust instead of requiring constant visibility.

They create systems that keep them informed without requiring them to be everywhere.

As technology continues to make information more accessible than ever, leadership value will not come from personally knowing every detail.

It will come from creating environments where people can think, decide, and lead with confidence.

Because leadership doesn't scale when everything depends on you.

It scales when your people are empowered because of you.

A question worth reflecting on:

What is one thing you could step back from this week that would create space for you to lead more intentionally?

07/23/2026

This morning I headed out on my road bike with something I rarely have. Time.

No meetings to rush back for.
No schedule to beat.
Just the freedom to ride.

So I chose a route I hadn't ridden in a while.

Halfway through, I discovered much of it had been torn up by construction.

Loose gravel.
Heavy equipment.
Roads that simply weren't meant for a road bike.

I had a choice.

Turn around and retrace every kilometre.

Or let go of the route I'd planned and find another way home.

I chose the second.

It wasn't the ride I'd envisioned.

I spent more time on rough roads than I expected. My speed dropped. My average power wasn't where it normally is.

At first, I found myself frustrated.

Then I caught myself.

I was still measuring success against the ride I'd planned instead of the ride I was actually having.

So I reset.

Instead of chasing speed, I focused on distance, enjoying the ride, and getting home safely with my bike intact.

The ride didn't become worse.

It simply required a different definition of success.

It reminded me of conversations I have with senior leaders every week.

A leader hires me because they're convinced they need to leave their organization.

Through coaching, they discover they don't actually need a new job.

They need a new perspective.

Another leader becomes deeply committed to a strategy, a sales target, or a plan that made perfect sense six months ago. The market changes. The team changes. New information emerges.

Yet they keep pushing in the same direction.

Not because it's still the best path.

Because they've become attached to the original plan.

There's an important distinction.

This is a leadership gap I see more often than people realize.

Commitment is a leadership strength.

Attachment can become a leadership blind spot.

Many high performers have built successful careers by following through on what they say they'll do. Perseverance matters.

But somewhere along the way, some begin to believe that changing course means they've failed.

It doesn't.

The strongest leaders I've coached know that changing direction isn't the opposite of commitment.

Sometimes it's the highest expression of it.

They gather new information.

They challenge their own assumptions.

They adapt without losing sight of the outcome they're trying to achieve.

Sometimes your values evolve.

Sometimes your business evolves.

Sometimes you simply learn something you couldn't have known when you first set the goal.

Changing your approach isn't giving up.

It's making a better decision with better information.

One of the biggest leadership gaps I see isn't a lack of commitment.

It's being so attached to the original path that you stop seeing better ones.

Are you still committed to the outcome, or have you become attached to the path you originally chose to get there?

Leadership Gap #3 -Confusing commitment with attachment.

Great leadership isn't about sticking to the original plan, it's knowing when the plan should change.

A Jacked Experience

09/22/2026

09/14/2026

09/08/2026

09/01/2026

08/25/2026

08/18/2026

08/12/2026

08/05/2026

07/30/2026

07/23/2026

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