Why (or how?) I chose Guild
I was looking at the three most common questions I've received after joining Guild (don't read too much into this, there are not that many people messaging me).
Do you have a job for me?
Why didn't you go and be a CEO somewhere?
Why didn't you just go to <insert big tech company here>?
I first want to thank the people who ask me the last two, and others of that ilk. It's great for the ego to think that someone out there believes that I can just make the choice to go and be a CEO somewhere. In reality, the somewhere has to also determine that they want you, but I appreciate the vote of confidence. Boeing - feel free to get in touch!
The first, especially when it comes from people I rate highly, is a tremendous compliment to Guild. It speaks volumes that they look at the story and are keen to explore being a part of it. It's a nice implicit endorsement of my choice.
Which brings me to the point of this post - why, or perhaps how, did I make my choice? Every choice I make is the right choice at the time and under the prevailing context (maybe something to explore in a future post), even if being human, we're all tempted to only judge after the fact, in the way that winning the lottery can sometimes make buying a ticket look like a rational decision (hint: it isn't).
I've been around for the best part of half a century, and I don't yet have a handle on what truly constitutes success in life - whether over a microcosmic period, or the span of an existence. I am clear though, that success is much like happiness. You won't have it all the time, and acknowledging and accepting that is essential to your hopes of achieving this. As sport has always taught me, the moment you think you've achieved and have it all figured out is precisely the moment you are done.
What I do have a handle on though, is my life context, and what really matters to me. Like most everyone, my family and I have stuff to deal with. We're not special, but everybody's stuff is part of the context in which they operate. As such, my exercising of choice over a career decision is entirely about me and cannot and will not match yours.
In my younger years, I might have had a massive spreadsheet of pros and cons, and another one of financial calculations. Today, I ask myself six questions, and for each, I have a point of view of where they should end up.
WHAT am I going to be doing?
The worst advice that I see people giving, usually only after they themselves have achieved an (unnecessary) level of wealth, is to "do what you love." This is nonsense. If I did that, I'd be a failed soccer player living on the street (I love it, but the absence of both skill and discipline would be a problem).
Instead, I aim to "love what I do." Meaning that I don't have to be fulfilling my childhood fantasies, but I do have to look at what I am doing and find a way to love it. As I get older (wiser?) that increasingly centers around believing that the product I'm selling actually matters.
I may have conned myself into that state of mind once or twice in the past. When I was younger, I sometimes looked for that love in the wrong places (not a life commentary, just talking about my professional choices).
As I made this next career decision, I was very clear that I wanted to work on a problem that I believe matters. More pointedly, it was important to work on something that mattered to me - absent that it's very difficult to truly be cause in the matter. Guild covered these bases, with the added bonus of what we do impacting people who genuinely need the lift.
WHEN will I be doing it?
I'm living my journey, not anyone else's. I don't compare my life with others', rather I just aim to live the life I'm interested in living. In doing that, I eschew all talk of work-life balance. That phrase is almost depressing to me. I have no interest in work that feels so much like work that I feel the need to compartmentalize it carefully away from what I consider to be my life, in order to ensure that I give my life enough time.
My life has many components to it. People. Cricket. Manchester United. Food. Dessert (separate thing from food). Travel. Planes. Good (Bad) Jokes. Work is just one more piece of that puzzle. I want all of that to be in balance, and I want everything that I spend my time on in life to be important to me. I am fortunate enough that I am not living on the edge and can have all these things in my life, so my perspective is related to my context.
I don't measure my hours at work, and I don't want anybody else to measure my hours at work. I don't mind working on a Saturday, and I don't mind watching Kobbee Mainoo snatch a 4-3 victory on a Thursday afternoon (although in this case I had to watch it later having avoided the internet for several hours, and have watched it countless times since).
My life encompasses all these things, and I keep my life as a whole in balance. The day I feel I have to carve out work in contrast or conflict with the rest of my life is the day I leave that job.
It's important to note that what worked for me a decade ago wouldn't work for me now, and what works for me now, might not work for me a decade from now. The knowledge of where I am in life, what I need, and what I'm dealing with, is a massive factor in choosing what will keep me in balance and what might not.
WHO am I doing it with?
I genuinely understood this too late in life. Who you spend your time with (and it's a quarter or more of your time that's spent with your work colleagues) has a profound impact on you. Chose well, and there's a remarkable additive value to all facets of your life. Choose poorly, and the impact is far reaching. For me, this boils down to:
A group of people with whom I can be authentic
I've landed on a simple truth - I am most effective as a leader when I can lead naturally and authentically.
A group of people from whom I can learn and who can help me continue to grow
That doesn't have to mean people who have been there and done that more than I have. It means people who are going to bring to the table a perspective that will push me to think and challenge me to make better decisions
A group of people that can operate from a common ground of shared values
Not homogeneous culture, but values and principles that can manifest in different ways. Of utmost importance for me in making my choice right now was an organization that aims to be grounded in people-centricity and a basic humanity.
Note that I didn’t say that I’m looking for some new best friends.
Nowhere is perfect. Nobody is perfect. I'm clear on the flaws I can work with, and I'm clear on the ones that I'm not okay with.
WHERE is this company on its journey?
I'll use the classic rocketship analogy here. The common recommendation is to join a rocketship that's on its way to the moon, and learn by observing how that journey unfolds. That's useful advice perhaps when you're early in your career - though I personally believe that finding a garage that is building a new rocketship is where the fun and learning really is at.
At my current place and context in life, I'm very clear as to where I want to be on that journey. Guild is a rocketship. Some amazing people have tinkered in the garage, and built a rocketship that is sat on a launch pad. That in itself is an incredible endeavour, and most don't reach that point.
The next phase of the journey is to prime the ship, fuel it, and then figure out how to ignite it and manage it. We don't know for sure if we're going to the Moon, to Mars, or across the whole solar system. With apologies for mixed metaphors, that's not the North Star, it's about how we get there.
That's what I am pumped to be a part of.
WHY will this get me out of bed every morning?
I often talk about my alarm clock test. Do I need an alarm clock and a few snoozes to get me out of bed in the morning, or am I going to be chomping at the bit to get up and go without external stimulus. Leaving aside my night owl tendencies and need to make sure I don't oversleep, this is key to me assessing my motivation.
Over time, I've come to realize that key to that, for me, is an element of uncertainty and discomfort. This is tightly connected with the "Where" above - I'm not going to get out of bed excited by a solved problem. I don't say this with pride - I have often struggled on the cricket field if I believe a game is of no consequence, and that's not a great attitude to have. I'm always working on that, in order that I'm not letting other people down unfairly, but I definitely relish beating the odds.
I may want more of a sinecure at some later stage in life, but I'm not there yet.
HOW will I fit into all of this?
I don't have to be the CEO for all of the above to add up. If I did, I wouldn't be at Guild today. Don't get me wrong - I've been a CEO before at small scale, and it would be a rational or logical move. And i have more than enough ego to believe in myself to play that role too. Again, Boeing, feel free to reach out!
I also know what I can and can't handle given life context, and more than that, I know what is truly essential to me in the role I take on. It comes down to two things.
The first is that I want to be in a position that requires genuine leadership, not just management. This again ties back to the Where and Why above. There's probably a whole separate post about this one day, but management is about executing on a path that is laid out. Leadership is about empowering and enabling people to go places they weren't already headed to and might not even have thought possible.
The second also ties back to the Where, and it's that it's important to me that my decisions matter on a daily basis and that the trajectory would be different without me. Experience tells me that that is rarer than one tends to think. Of course, A/B tests aren't possible until we unlock the key to the multiverse, but the rocketship being on the launch pad versus already headed for the moon is what allows for this possibility.
I've made a very active choice to join Guild. My first month suggests that it's going to be the ride I was looking for across everything I've just outlined here. That's invigorating. I'm excited - not just for the amazing things that will eventually happen to the world, but for all the ups and downs and accelerants and speed bumps that we'll encounter on the journey ahead. That's what I'm here for. Time will tell, but there’s a real shot at finding my ikigai here.
Good luck with the new job!