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Sabbatical: Thoughts on Exiting and Re-Entering InfoSec

In 2018, I stepped away from working for 7 months. The reasons were personal but largely burn-out-related (you can see it in this site's activity, for example). That being the case, if you had told me 20 years ago that I’d be in a position to walk away from working and everything would be ok, I’d have told you that you’re crazy and that future Me must be very fortunate and/or lucky. I know the latter is definitely true.

While my time away wasn’t perfect and I didn’t do a number of things I wanted to do or planned to do, I walked my son to school every single day and was there to pick him up every day. I read a lot of books and played a ton of hockey including one day when my son and I spent 4 hours on the ice. Again, I’m incredibly fortunate.

What I learned.

Dream, Plan, Prepare.

You’ll need to plan your time off carefully. School, jobs, mortgages, or rent, will need to be considered. You need to plan and understand what it will take to pay for the things that need to be paid for and manage the things that need to be managed. When you think about what it is that you’re going to do with your time, I’d encourage you to dream big. See what it would take to take that year off in Mexico or Spain (as an example) and plan accordingly. But plan in advance; far in advance! Don’t wait until the last minute because if you have a family or other obligations, odds are, it’s going to be difficult to pull off. Oddly, having the money to make it happen is the easiest concern to address.

Personal Care

Exercise, limit video gaming, read, and do “personal care.” It’s important to do this sort of thing, generally, in normal times. But while on a break, I found it essential. As I wasn’t traveling (we did make a few trips to see relatives) I identified, early on, the risk of falling into a rut and developing really toxic habits while not doing work work. Habits like sleeping late, not exercising, letting my mind decay, losing touch with InfoSec, and losing a general sense of mindfulness moved to the fore as threats to guard against.

My suggestion is to first, be aware of your own habits and risks of things like depression, obesity, and laziness. I was VERY aware of numbers 1 & 3. To manage it, I was up and out walking my son to school. I usually had a good meditation session in the AM or took a walk where I focused on breathing and mindfulness. I limited alcohol and drugs. I made sure to play hockey, cycle, and run and purposely metered my time playing video games. I even took on a few minor projects around the house.

Re-Entering the Market

Your Network

I’ve written before about the value of your network. Even though I've previously placed a really high value on cultivating a professional network, I realize that I was understating it. To be blunt: your network is everything. It is the only thing that matters. There is nothing else except your actual skill set that matters 1. While away, I kept in touch with people, and in coming back, the only opportunities I had were developed from my network. Period. While not everything panned out, there was nothing else worth shaking a stick at.

Everything is transactional

If you know me (few do) or have spent time with me, you know I have a fairly dim view of people. Perhaps it’s my proximity to Sales or the InfoSec industry. I don’t know. What I’ve said for several years is that most things and most people are transactional. I stand by that even today. What I found during my time off and my time returning is that many people, when they had nothing to gain, wouldn’t take my calls or never delivered on introductions or referrals. I’ve had people, when closing and implementing $1.5 mil of tech refer to me as “my good friend” but when I need to check a reference or get a bit of intel on a role, can’t call back. I found that time and time again. I still do.

Are there real friendships in our industry? Of course! Do people get along and have warm and friendly collegial relationships with others? Naturally. But my experience was and has been that most people are transactional. You should be prepared to experience what I did.

Companies are Flakey

If you’ve ever interviewed for a job you already know this. This is barely worth noting but it’s something you have to wrap your mind around as you mentally and emotionally prepare to begin the journey back.

When you talk to a hiring manager about a role, there’s a good chance you’ll never hear back from them. This is especially true of Human Resources. This highlights the absolutely essential nature of your network. Every single job offer or firm lead I had came from within my network, and except for two firms, every single one of those organizations conducted themselves with class and professionalism.

Bonus Season = Quitting Season

You may already know this; you may not. Most yearly bonuses are paid out at the end of March. This is especially true in the financial services industry. Additionally, many managers have their headcount requests approved in February and March. This means if you’re in the market - let’s say, you’re returning from a sabbatical - March and April are going to be the months where things really start to open up.

If you’re counting on landing something in December and January, you’re swimming against the stream.

Recruiters: Limited value, Increased risk

Potentially a dicey topic but I’m going to put it to paper anyway: be very careful when working with recruiters. For the vast majority of recruiters, you are the commodity. There are very, very few recruiters and recruiting firms that you should engage when you are ready to return. And to be honest, I haven’t productively worked with one in years and every interaction I’ve had with a recruiter since 2013 has been a waste of time or worse.

Unless you have a close, working relationship with a recruiter or a recruiting firm, my advice would be to steer clear of them.

In conclusion, should you step away from your career; InfoSec or otherwise? That’s up to you. Can you? You certainly can. It’s important to plan and be prepared for both the time off and your inevitable return.

My hope is the preceding thoughts and bits of advice will help you enjoy your time off and speed your time back healthily and productively.

Notes and Comments:

  1. And let's not pretend we don't all know people with highly effective networks and limited skills. Hell, I'm sure people put me in that category!

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