This week on Random Access Memories, I'm diving into my conversation with Tim Chase, Field CISO at Orca Security. Tim spent years working towards becoming a CISO before making what many people see as an unusual move: leaving operational security to become a Field CISO. But this wasn't really a conversation about career titles. We talked about identity, burnout, trust, knowing when to say no, and why every successful career quietly asks the same uncomfortable question:

What are you willing to miss to build it?

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The career you dream about isn’t always the one you’ll love.

Tim spent years trying to become a CISO. Then discovered his favourite part wasn't running security, instead it was helping other CISOs solve problems. Sometimes success is having the courage to admit your dream has changed.

Trust is built long before anyone buys anything.

The best Field CISOs don't sell products. They solve problems. Sometimes that even means telling a customer, "We're not the right fit." Ironically, that's often the moment trust is built.

Every yes has a no attached.

Every conference, customer visit and keynote sounds exciting until you realise what sits on the other side of the calendar. Black Hat means missing the first week of school. Another business trip means another bedtime missed. Careers don't just cost time. They cost moments.

The people who shout are the one you should listen to most.

One of Tim's best insights came from difficult customers. Instead of arguing, he learnt to understand what was really frustrating them. Technical expertise earns credibility. Emotional intelligence earns trust.

Don’t let your job become your identity.

Operational CISO. Field CISO. Advisor. Leader. They're just roles.

The important question isn't "What's next?" It's "Who do I want to become?"

We spend years chasing job titles that we barely stop to question whether we actually want them. Tim Chase did exactly what most ambitious security professionals hope to do…He became a CISO. Years of hard work, leadership and technical experience finally paid off. But once he'd reached the destination, he discovered the thing that fulfilled him wasn't sitting inside one organisation. It was working with hundreds of them. Teaching, learning, speaking and becoming a trusted advisor to other CISOs became the part of the job he couldn't stop thinking about. So he left the role he'd spent years chasing to do the work he genuinely loved. That isn't failure. It's self-awareness.

Don't spend your life proving you can climb a ladder you no longer want to be on. The bravest career move you'll ever make might not be a promotion. It might be admitting your definition of success has changed.

This week's podcast with Tim Chase left me staring at my calendar.

Tim and I spent an hour talking about life as a Field CISO, but the conversation wasn't really about conferences, customer meetings or security. It was about trade-offs. Every keynote, every customer dinner and every flight sounds exciting until you realise what sits on the other side of it. A missed bedtime. A football match. A date night. The first week back at school.

Earlier this year I looked back at my diary and realised I'd spent thirteen consecutive weeks travelling between the UK and the US. Some weeks I flew multiple times. At first, I wore it like a badge of honour. I was speaking at conferences, meeting customers and doing work I genuinely love. Then one evening my kids asked a simple question: "Do you have to go away again?"

It wasn't guilt they were trying to make me feel. They just missed their dad.

That conversation changed how I looked at my calendar. Every booking wasn't just another opportunity. It was also a decision about something I wouldn't be present for at home. Tim talked about missing the first week of school every year because of Black Hat. I've missed school plays, football matches and evenings I'd much rather have spent on the sofa with my family than in another airport lounge.

The uncomfortable truth is that work will always give you another opportunity. Your children won't always be this age.

Every yes has a no attached:
We celebrate saying yes to promotions, conferences and exciting opportunities. We rarely stop to ask what we're saying no to. Every commitment fills part of your calendar while quietly emptying another. Make sure you're choosing both sides of the equation intentionally.

Success isn’t measured by how full your diary is:
There was a time I'd judge a good month by how many flights I'd taken or stages I'd stood on. These days I'm trying to judge it differently. Did I make the school play? Was I home for dinner? Did I get to coach football? The answers to those questions matter far more than my LinkedIn profile ever will.

Your family don’t need more of your time. They need more of you:
Tim said the key is making the most of the time you're home. I think that's exactly right. Being physically present while mentally answering emails doesn't count. Sometimes the greatest act of leadership is closing the laptop, putting your phone away and giving the people who matter most the version of you they deserve.