Look, we need to talk about the elephant in the room: being a security leader feels like trying to juggle chainsaws while riding a unicycle on a tightrope. Over a pit of angry developers. In a hurricane.

But here’s the thing – you might not actually be doomed to fail! Wild concept, I know. Pour yourself a coffee (or something stronger, I don’t judge), and let’s chat about surviving this circus.

The “10” Steps (Because Arbitrary Numbers Make Things Official™)

1. WDTLPD (What Did The Last Person Do?) – Because sometimes the best strategy is learning from other people’s mistakes instead of making exciting new ones of your own.
2. Where Are All the Bodies? – Not literal ones (hopefully). Find those hidden technical debt graves and skeletons in the infrastructure closet. Every org has them, like that one Windows 2003 server nobody talks about.
3. CYA (Cover Your… Assets) – Document EVERYTHING. If it’s not in writing, it didn’t happen. Think of yourself as a bureaucratic squirrel hoarding nuts of evidence for winter.
4. The Risk Acceptance Dance – Find the scary gaps, write them down, and get executives to sign off on them. Nothing makes people pay attention like their signature on a document that basically says “I knew about this potential disaster and chose to do nothing.”
5. Know Your Battlefield – Understand your constraints. Maybe you have the budget of a lemonade stand but the security needs of Fort Knox. Cool cool cool cool cool.
6. Gap Analysis: The Sequel – Like regular gap analysis, but with more existential dread.
7. Accept That You Can’t Win Everywhere – You’re a security leader, not Doctor Strange with the Time Stone. Pick your battles.
8. Be The Security Leader They Need – Not the one they want. Sometimes you’ll be the party pooper. Embrace it. Get a cape that says “No” on it.
9. Details Matter – The devil’s in there somewhere, probably exploiting a misconfigured S3 bucket.
10. Focus on Real Threats – Yes, quantum-powered AI hackers from Mars sound scary, but maybe fix that public RDP port first?

The First 100 Days (Or: How I Learned to Stop Worrying and Love the Chaos)

• Find out who’s who in the zoo (stakeholders)
• Learn what makes the money machine go brrr (business understanding)
• Figure out where all the money goes (budget reality check)
• Assess the current dumpster fire situation (state assessment)
• Understand what everyone expects (requirements gathering)
• Show value before they start questioning your existence
• Start discovering things ASAP – can’t defend what you don’t know exists!
• Learn the risk appetite (spoiler: it’s usually “yes” until something bad happens)
• Identify crown jewels (the stuff that keeps the lights on)
• Learn the legal stuff (because prison orange isn’t your color)

Initial Discovery (AKA Digital Archaeology)

• Read ALL the docs (yes, even that 200-page audit report from 2018)
• Run those discovery tools (and pray they don’t break anything)
• Make friends! HUMINT is key. Bribe with cookies if necessary.
• Get that sweet, sweet intel (threat intel, office gossip, whatever works)

Preparing for a Really Bad Day

Because it’s not IF but WHEN something will go sideways. Some key questions to ask:

• Are our backups actually working? (Not just the “yeah probably” kind of working)
• Can we recover if everything goes boom?
• Do we have a plan that doesn’t start with “panic”?
• Have we tested any of this? (And no, thinking about testing doesn’t count)

The Never-Ending Story

Remember: security leadership is a journey, not a destination. It’s like a game of whack-a-mole where the moles are getting smarter and someone keeps giving them new tools.

But hey, if you’re reading this, you’re already doing better than most. Keep fighting the good fight, document everything, and remember: sometimes the best security solution is a well-timed facepalm and a deep breath.

Stay caffeinated, my friends. You’re gonna need it. 🚀☕️

P.S. If all else fails, you can always try turning the entire infrastructure off and on again. (This is a joke. Mostly. Unless…)