I really enjoy speaking at conferences, for four main reasons:

• It helps me learn subjects more completely and solidify my own thinking
• Hopefully I have something to say that will help someone else
• I get to meet and interact with new people
• I think public speaking is just kind of fun

You may notice that three of those reasons are selfish. I noticed that too, and I worried that I was wasting other people’s time — both the conference organizers and the participants — just to do something I thought was fun.

So when the next BSidesSLC call for speakers came up (I’ve spoken at BSides events here in Utah a couple of times) I spent a lot of time trying to think of whether or not I had anything actually helpful to say. BSides are typically aimed at people who are new(er) in the field and I’d spoken before about how to write good documentation, as well as what a “day in the life of a blue teamer” is like, which were both subjects that I felt were helpful and probably weren’t going to get talked about much (most cybersecurity conferences tend to lean towards red team stuff).

I spent a couple weeks proposing (to myself) and then discarding potential subjects. Finally I landed on the subject of Career Capital from Cal Newport’s book “So Good They Can’t Ignore You” — I wrote about it a bit when I reviewed the book, and I found in mentoring meetings that it was a subject that came up a lot.

I thought it would be interesting to survey other leaders to find out what kind of “Career Capital” they valued most (for example, was a highly specialized certification more valuable than a degree? Was X number of years of experience more valuable than either of those things?) and then give a talk where I introduce the subject, outline the results of the survey, and then talk about how someone new in cyber might use opportunities to build career capital to get them closer to the career they want, faster (although probably not as fast as some popular ‘HOW TO BREAK INTO CYBER’-type posts would have you believe).

I submitted the talk and a week or two later I heard back. They had way too many proposals for speakers and didn’t want to do mine for one of those limited slots, but they wondered if I’d like to turn it into a workshop (which is a more interactive, longer, drop-in/drop-out type experience).

I wasn’t sure if I could make the subject matter work as a workshop, so I told them I’d see if I can figure it out and get back at them. I thought about it and decided to write a few blog posts to dig deeper into the subject to see if there was a way to make a really good, interactive event out of it.

“Where do you want your career to go” is a harder question to answer than it appears

I wrote this blog post, pitching at as the first in the series, to get some of my first ideas down. I figured I’d follow it up with more blog posts as I narrowed down the subject to what would work interactively (I know blog posts aren’t interactive, but often as I write blog posts I’ll think of activities that illustrate the concepts).

By the end of that first blog post I pointed out that before you can use career capital to get where you want you have to know three things:

1. Where you ultimately want your career to go
2. What major stepping stones for your ultimate goal are
3. What career and social capital is helpful in getting you to those stepping stones

Obviously the next blog post should be about these three items, and maybe even just focusing on that first one — where, ultimately, do you want your career to go?

So I started thinking about that — I had a conversation with a coworker about whether it’s better to have a definite goal or to be open to whatever opportunities come, that lead me to think about my own career which has been much more guided by opportunity than by direction from me.

And if my career was guided by opportunity, what good was question number one? Wouldn’t having a strong answer to that just block you off from further opportunities? Or was my career the result of nothing but luck and I truly didn’t have anything to teach anyone about building a career because it would be impossible to replicate my own success???

Enter the existential crisis

The past year or so at work has been difficult for me — new responsibilities, new challenges, etc. etc. As I was working through all this in my head I realized my own career was at a crossroad.

(You could argue that careers are perpetually at crossroads since, at any time, you can choose to dramatically change what you do as long as you don’t mind starting over and getting a major paycut)

I’d been moving from opportunity to opportunity, doing my best at every stop, but ultimately what I did was driven by what was in front of me, not what I was choosing to do. I needed to figure out what I actually wanted — what I would choose to do.

I grabbed a laptop, opened a word doc, and answered these questions:

1. What things do I enjoy and/or am good at?
2. What do I feel is unique about me?
3. What is most important to me?
4. What career capital do I have?
5. What do I wish to accomplish professionally?
6. Next Actions

The top four I responded with bulleted lists, but for question five I wrote several paragraphs and then also wrote a bullet list with “bucket list” type work items (for example: “I would love a position that allows me to more fully experiment with things like work structure, pay structure, team makeup, etc”).

I felt a ton better after writing this down. I asked my wife to read it and she suggested some additions and changes. Then I scheduled time with my boss to talk about it with my current role and he graciously made time for me and listened to me, then he talked about what we could do in my current role as well as future opportunities.

I do feel my boss is pretty amazing and a lot of managers wouldn’t take the time to talk something through like this. And some of his thoughts weren’t exactly in line with what I wrote down, but because I had written stuff down I could see how it did and didn’t relate to what I wanted to accomplish.

I feel like this was a really beneficial exercise, and I recommend anyone reading this who isn’t sure where they want to go with their career to do it — as long as you realize that opportunities that arise outside of the paper may actually be better than what you write down.

That’s fun — Still not a great workshop, though

I know! I feel like this is better as something someone does on their own, or potentially with a mentor (or review it with someone you trust after). It’s not a great workshop for a cybersecurity conference, though.

BUT, I’m ultimately grateful that I studied all this at this exact time and worked through all this for myself, and hopefully it’ll be helpful for you.

PS — I’m really excited to go to BSides as an attendee and see all the great speakers they have lined up (if you’re in the Salt Lake area I highly recommend it).