Something needs to change.

More freedom.
Better direction.
Your terms.

Private Direction

For capable men who know something needs to change.

Leo Cunningham smiling at his workspace

Grounded in the present. Respectful of the past. Hopeful about the future.

You’ve achieved so much. Now you must put your time and energy into what deserves it the most—and that includes you.

Private Direction with Leo gives you somewhere independent to rebalance and take action.

Book a private conversation

Free · 20 minutes · By phone or video

You’re carrying a lot.

Maybe the business. The team. The family. Expectations from all around, financial pressures, admin and decisions that keep arriving every five seconds.

Pushing harder alone won’t create a better direction.

Together, we’ll make room to think. Work out what matters now, explore your possibilities and test them against real life — then chart a course you can feel good about.

You don’t have to tear down what you’ve built. You need more room, more choice, and a future you actually want to move towards.

Judgement paid for
in actual living

Leo Cunningham

I’m Leo. Over thirty-five years, I’ve worked across finance, tech and advertising. I’ve created start-ups, run businesses, led teams and had my fair share of failures — or learning experiences, as they’re called now.

Alongside the career came marriage, divorce, family, getting older and changes I hadn’t planned for. I know the pressure of keeping things moving while trying to work out what comes next.

I also know what I wish I’d had: someone with experience, perspective and the willingness to tell me what they actually thought.

That’s what I bring to Private Direction. A background in human behaviour and strategic thinking, grounded in the business of living.

We’ll take your circumstances seriously — and give your possibilities some proper attention.

Find out more about Leo

Let’s talk about
what comes next.

You don’t need a finished plan. Bring what’s on your mind, what you’d like to change or something you want to pursue.

We’ll spend twenty minutes talking it through and see whether working together makes sense.

Book a private conversation

Free · 20 minutes · By phone or video

If I think there’s something we can work on, I’ll invite you to a first 90-minute working session. That session is on me. No charge.

Looking for a coach
or mentor?

You may be looking for clearer direction, a fresh perspective or someone experienced to think things through with. That’s a useful place to start.

Private Direction with Leo gives you room to explore what you want next—and work towards it with judgement and direction you can make your own.

Before You Hire a Coach →

Field Notes

Written from real work. On burnout, separation, identity, judgement, success — and finding solid ground again.

Attempts to understand what happens beneath the surface—and what may still be possible from here.

EXPLORE PRIVATE DIRECTION
“My job is to help you see more clearly, work out what’s worth pursuing, and move towards it with confidence. The direction is yours. I’ll bring experience, judgement and a willingness to tell you what I think. Then, when the time is right, get out of your way.”

Private Direction

Book a private conversation

Free · 20 minutes · By phone or video