Coaching and Empathy - Andy Skipper

A lot of people hope that there will be a single thing that they can tweak in their life or a single set of actions they can take to overcome some very baked in feelings about how they work with people or how they interact with people, how they build cultures or build teams or whatever. And they do need to go off and do a bit more touchy-feely stuff and get back into that understanding of where they've come from as an individual and what their hangups are. That could be difficult to stomach, especially first timers, that's very common.

What work do you do to create work for others?

Well I suppose as in my current role as a business owner, fundamentally I have created a series of opportunities for people to work and also for a bunch of very, very generous volunteers who are members of the community that I run who are actively helping us build something bigger. But in terms of shaping the kind of work that they do, I think probably I help most somatically, but also as a mentor and as a point of knowledge in terms of community and work life balance and all that stuff. I have a lot of experience supporting other people going through those journeys as well. I think that's it basically. But I have very strongly held beliefs about the importance of a leader in terms of creating a culture of compassion. I think compassion is a large part of how you create a team that gets to their best work, if you want to put it that way.

You can't really create an environment for people to produce their best work without being highly individually compassionate to each of them. I think a lot of leaders miss out on that and they think of the group as entirety and not think about the individuals and their personal needs and so on and so forth. My personal leadership style is very much coaching centric, I would say, which is how I became a coach and how I started CTO Craft as a community. My preference is always to focus on building up individuals within a team while not losing sight of overall performance and productivity and all that sort of stuff.

Why is compassion so important to you personally? Where does that come from?

It's a really good question. I think same as anybody else, I have a specific set of experiences from my childhood. I have points of reference from my parents. I've been in situations where I haven't been led with much compassion that have stuck with me.

Like what?

Like what? Certainly I've worked under some very, very authoritarian and absentee leaders in the past, which has been quite damaging in a way. I've also been in businesses where there has been more pressure than really there needed to be from founders and from the board of directors and so on and so forth.

Is there an example that sticks in your mind?

Yeah. Let's see. When I was an engineer, so way back in the day, I took my first London based role back in whatever it was, 2005. And without wanting to name any specific companies or individuals, I think the leadership there was very agency like, in that they were quite old school, they were very focused on building personal brands. They were very focused on pushing stuff out of the door very quickly, and they weren't particularly interested in the team and the people within the team other than to socialize and go out for drinks with and so on and so forth. And then that meant there was all the more pressure on the individuals within the team to go the extra mile to perform outside of their comfort zone, which is great, that's fine, but you need some support in doing that. You can't do that to say a bunch of individuals.

Again, without wanting, wanting to name any specific people or any companies, I felt that I was having to fill in the gaps a little bit. And that's in a way how I found myself moving towards leadership roles, because I supported the other engineers in the team. I took on a bit more of a mentoring role without getting any of that support myself.

It's interesting that when I asked you that question, where does that compassion come from? I did so almost expecting you to say what you said, which was I had a boss that was difficult. I had a leadership style that didn't really run in the way that I wanted and I reacted against it. It's interesting that, I guess there are two scenarios where that could play out. One is you're inspired by another compassionate leader that you want to emulate, and the other is that you react to a negative experience you have. And also often it's a reaction to the negative rather than a duplication of the positive.

Sadly so. Sadly so. I think the chances of ending up in a business where the leadership and the culture is exactly what you wanted is very slim, especially in your first role I think. You are very, very lucky if you end up in exactly the situation you want to be in culture-wise.

You said that there were moments from your childhood that have inspired your compassionate leadership style. What times resonate most?

I'm not sure if there are any specific times, but both my parents are incredibly generous and compassionate and thoughtful and very warm and fuzzy in a literal sense when it comes to my dad. I think that's also my extended family. They're very socially aware, I'd say is a good way of putting it, but they're also just very nice people. I think it quite literally boils down to me growing up around people who wanted to help other people and cared about other people and were just very generous and sweet natured and so on and so forth.

How was your view of work and then your eventual choice of work impacted by your parents?

That's a really good question. Neither of my parents are particularly commercially minded, I would say. I think I was a bit more commercially minded when I was in my early 20s, which is how I got drawn I guess towards startups and eventually created my own businesses. I think I probably needed to build a bit more of a thick skin than they have or they had at the time at least. I see that generosity and that niceness as a massive backbone of what I do and how I do it, but I did have to fight against it in some ways. I did have to build some of my own life skills. I did have to build some of my own social patterns and so on, to be able to do it like this

Because they were so compassionate that they were so warm and fuzzy.

I think so. I think that's fair to say. Not to say they were gullible or weak or anything like that, but I do think they would've needed a bit more of an edge to do the kind of things that I've done.

It does beg the question, where did that edge come from and why did you not also end up, not that there's anything wrong with it, being warm and fuzzy?

It's a really good question. It's a really good question. I think those formative experiences in the companies that I was working with probably make a difference. I think I probably do have a bit more of an edge naturally than my parents do, in that I may be a bit more suspicious than they are and maybe a bit less risk averse as well, I would say. I'm not sure entirely where that comes from, but certainly I use that to hone my edge, I guess you would say. I think leaving home, going to university and all that stuff gave me a whole load of different perspectives as it does with everyone basically, and more exposure. I think I was lucky in my early days that I got exposed to a lot of people that I saw who were successful entrepreneurs and blossoming and creating value for other people and so on and so forth, and who had behavior patterns that were very different from what I'd experienced in my family life.

I think also there are certain aspects of my family life, my childhood, that I pushed away from quite heavily. When I was growing up, for example, my dad is agoraphobic, and we lived on a small holding in the middle of nowhere in West Wales. There was an element of wanting to both escape that but also avoid that when I was older. I think that did push me towards the more edgy, businessy, more commercially minded people as friends and as people that I wanted to work with. I think that's true. I think that's true. I think I am just a slightly more edgy, neurotic person than my parents are, put it that way.

Naval Ravikant has that story about the elephant and the unicycle where if you could walk down the street and you see an elephant, it's like, okay, right? It's an elephant. If you walk down the street and you see a unicycle, it's like, okay, right, it's a unicycle. But if you walk down the street and see an elephant on a unicycle, you're like, what the hell's going on here? And almost as if, how on earth could you have these contradictions exist in the same place? And as you were talking through both that warm and fuzzy side and your edge, it feels so visual and so tangible. One is literally the edge of an object and the other is something soft. And as you were talking it reminded me of this almost this subtle search that I think some of us pick up on our working journey where we recognized that the contrarian is not necessarily a bad thing.

And though it might be unusual, it can also be hugely beneficial because somehow you are able to mix disciplines and you can see things on the edge. And as you explain that, it almost felt like the meeting point between those two contradictions.

I think so. I think that's right. I think self-awareness is a big part of success and this kind of leadership role. I think it's being prepared to look at where certain aspects of your personality and your emotional state come from. I think a lot of first time CTOs or first time leaders that I work with, they haven't quite reached that state of self-awareness. And so they're still very, quite often, at least they're still very fixed in the individual contributor, autodidact, self-sufficient solo problem solver mentality where they actually have a lot more going on under the surface that lends itself more to leadership and culture building and so on and so forth, that they need to draw out of themselves a little bit.

I think that's why a lot of people go for coaching or therapy or join professional network groups like CTO Craft and that kind of thing. Also I'd say fundamentally there isn't a right or a wrong balance of the edge in the softness. I think it can be a lifelong quest to try and find the right balance if you have both of those in your psyche. But I don't think there's necessarily a single sweet spot then. And that sweet spot is going to change throughout your life anyway, depending on what you're doing, where you're working. But it's a useful journey to go on at some point for sure.

If you don't think there's a specific sweet spot, is there a point in between the two that you optimize for?

Yeah, as I say, I think it's specific to your situation. If you are leading a team of 150 people and you've got three kids at home and so on and so forth, your sweet spot is going to be very different from if you are a 25 year old first time CTO leading a team of two in a co-working space and living in a bachelor pad.

That's fascinating because I so deeply remember when we were first starting cord, how awful I felt, because I felt I was so far away from that soft part of me. I felt I was being pulled the whole time to being on my edge and constantly behaving in ways that didn't feel like the truest version of me. Whether it was because I needed to get this project done or move on to this place or make this happen. It certainly helped as cord has grown that I felt I've been able to lean more into the softer sides and that's been a better suit of my character. But I remember so vividly at that point in time, and you're so right that different circumstances require different parts of it because it felt so alien in that moment not being able to feeling like it was out of kilter.

I think you get to a point where there is a danger of it being out of your control as well. I see a lot of startups whose founders they hang on as leaders of the company, well into the life cycle of the company while still being very edge focused. I don't know if that's the right way of putting it, but they're still very operational and executional and so on and so forth, where they should really be stepping back and looking at the health of the company and the culture and the bigger picture and they should have people that they delegate the operational and the execution to. I think you have to take control of when that sliding scale moves. It does can't just happen naturally. It needs to be a lever that you pull.

You said that self-reflection is one of the big things that has helped you but also has helped some of the CTOs that you've coached. I'm sure you get this a whole lot. What are the tangible benefits to a CTO of doing that coaching and what's the difference between getting a mentor who can tell me what type of architecture this type of thing should look at versus talking to someone about my own personal journey, my childhood? It's an understandable question. Why is me as the CTO reflecting on my childhood going to help my company grow? How do you answer someone in that scenario?

Well, first of all I'd say we don't generally step into childhood trauma and that kind of thing. I think if it comes to that point, generally we refer them to a therapist or something like that. It is purely professional coaching basically, unless there's an ad hoc conversation about a specific childhood trauma that's led to a certain type of behavior. But no, it is more about self-awareness and it's about personal change. I think having somebody who is familiar with the industry that you're working in actually helps quite a lot as a coach in that you're not mentoring them, you're not giving them the answers, you're not sharing how you would solve some of their problems, but you do have a different level, I guess, of empathy for the situation they're in, because you more than likely been in that situation.

But people come to us for coaching for all sorts of different reasons. Some of them want it as an ongoing thing to continue building their skills and to get around certain blockages that they've come across in how they do things. And some people have a very specific major challenge that's existential in some cases to them and their business. It's all manner of stuff, but it is all about personal and professional development rather than eeking out the progenitors of certain ways of thinking from their childhood or their relationships and so on and so forth. Yeah, very rarely bridges into that to be honest.

We're all looking to be the very best versions of ourselves, and your job is quite uniquely aligned because that is your job. Your job is to enable other people to be the best versions of themselves. An interesting question that I wanted to ask you is, what makes a great client for you? When someone comes to you, when you are assessing someone and you're trying to figure out like, wow, I could really help this person grow, or there are these big things that are going to stop me helping this person grow, what things go through your mind and how are you trying to work it out?

It's generally by the situation they're in and then by their personality. The way CTO Craft works, we've got a whole bunch of coaches that we share work amongst. There's an initial conversation that is had with the person to find out what kind of skills they want to build, what issues they have, what personality they have, what kind of personality they want to find in a coach. But for me personally I have specific areas that I will always pick up as a coach, which are things like burnout and personal wellbeing. These are things that I have experience in personally, so I tend to dive in with those because I can help people pretty quickly with that thing. I also jump in where they have inter leader relationship problems, for example.

I've done a fair bit of co-founder therapy thing, which is a bit like couples therapy. In terms of personality, I don't have a massive filter. I tend to enjoy working with anyone who comes our way, who's actively looking for help. I tend not to like working so much where coaching has been imposed on people, which does happen in some cases. We generally shy away from working with people in that way. But I prefer to know that somebody has actively gone out looking for support and that's my preference at least.

And is there a certain type of person where you feel like they're almost like a level beyond the normal person that you would look at? So almost someone where you think, not just that I'm going to help you solve your problems, but actually if we create a close working, coaching relationship, I can see that at some point in the future you will become X. Do you ever have that experience? And if so, what constitutes that person?

I think that it's my aspiration in every case, not as the exception that they'll all turn as something spectacular. In some cases, some of them eventually turn into coaches themselves, which is brilliant. I don't think there's a single criteria that I look for and will this person go the distance or will this person turn into X, Y, or Z? It can be dangerous to go looking, I think for specific people who you think will experience the biggest change. I think what I would prefer is to treat everybody as capable of taking those big next steps and doing big, big things and work backwards from there rather than looking for specific flags.

And it sounds like one of the big parts to that relationship is your own personal experience, and the deeper that personal experience, the more you can help that individual who might be going through something similar. What are the deepest personal experiences that you've had, that you know can help people through?

As I said before, I've burnt out at least once, probably twice in CTO roles. I've also supported people prior to being a coach formally in getting out of those burnout, death spirals. I guess that's been the biggest leading factor in me coaching. I've experienced huge amounts of pain and trying to do a good job as a CTO that I've rectified using my own personal resources. I think that's probably it. In my first CTO role, this is a very standard story. I was brought in as a developer. There was nobody there really to oversee development as a whole. It was a small team, it was a pre-product startup. I stepped in and got given the CTO title by default more or less. But I always say just didn't have any experience of leading teams or with the scale or the pace or the ambiguity of startup work.

I burnt out pretty quickly and stayed much longer than I should have basically. There were some extenuating circumstances. I had a house fire and lost everything and I cut the end of my thumb off during this time. It was a perfect storm. I basically took a year off after eventually sidling out. But it taught me a lot about what the factors were in me burning out, and it taught me a lot about how to avoid some of those factors, but also build a bit of a thicker skin so that I'd be able to deal with some of those external factors and compartmentalize and so on and so forth. I've taken that a lot into my coaching.

I'd love to break down some of the lessons that you found there. It sounds like extraordinary circumstances that you find yourself in a gift to the people you're now able to help, perhaps not at the time. If you were to, and I appreciate this is a very difficult question, get into the heart of the key learnings that you feel like you've been able to pull from that experience, what would they be?

Some of them are not mind blowing, they're so obvious in hindsight. But I think being kinder to myself was the biggest thing that I learned. I'm a very conscientious person, so when I jump into any projects, I absorb some of it into my personality, if that makes sense. I was very, very attached to this company. They'd given me a big chance, they'd taken a risk and given me the CTO title, they had just taken a series A, so they were being held accountable by this very famous set of investors, Brent Hoberman and Robin from LocalGlobe, et cetera, et cetera, and had a whole bunch of people you would definitely know to speak of on the board of that company. I just told myself at the time that I needed to be perfect at everything and I didn't give myself any space to make mistakes.

And at the same time, because of the compassionate, softer side of me, which I spoke about before, I was making sure that everyone that worked for me got those benefits. I was being the proverbial shit umbrella and making sure that they had all the benefits of being protected from the stress and the ambiguity and so on. And at the same time I was not just absorbing all of that stress and ambiguity and pressure, I was also putting pressure on myself. It took a bit of introspection during that year off to finally realize that I didn't need to be putting that pressure on myself, and I didn't need to be so protective of everyone else. That's more or less what it boils down to. It's a whole bunch of different lessons I take from it as well in terms of trust and picking the right people to delegate to and et cetera, et cetera, general leadership stuff.

But underneath it all is this feeling that you weren't kind enough to yourself in that moment?

Yeah, absolutely. I'd say of all the pressure that was on me as a CTO, at least 60 to 70% came from myself and my assumption about how much I should be performing and that was not healthy.

How do you know when you're being kind to yourself now?

That's a really good question. I think I've built a better compass. See now I know when I'm overdoing it. My situation has changed substantially since I was in that role. That was 2006, 2007. I now have a family. I have a wife who holds me accountable. I have a kid who I have to make sure I reserve some energy for.

How's your thumb?

Thumb still hurts. Thumb still hurts 14 years later. There you go.

Oh my God.

I'm in a different position, but also I have a chronic illness which popped up about eight years ago that I'm dealing with and which forced me to take a very exacting lens on what I was doing, how much I was doing, the relevance of what I was doing, et cetera, et cetera. I have to be a bit more focused and a bit more mercenary now.

When did you first find out you had a chronic illness?

That was beginning of 2014, so whatever that is, eight and a bit years ago. It was just after I'd left. I was the first CTO at made.com. I built them up, and was very happy with where I'd taken it to, wanted to do other stuff. I stopped working there in 2013 to take on fractional roles mainly so that I'd have more flexibility, time to spend with my son who'd just been born, and that kind of thing. And then I just started getting headaches out of the blue and problems with my sinuses. I immediately went in, had a bunch of surgery, had a bunch of therapy, physiotherapy, so on and so forth. And that really went on for about five years. And then during that time, I'd taken on a role, so I was CTO at Comic Relief and I'd done a bunch of other interim and consulting CTO projects that were great fun.

I did a spy museum, I did a bunch of fashion related stuff, great fun. But all the way through this I was cycling through different medications and therapies and diagnoses and so on and so forth. And eventually, well still don't have a formal diagnosis, but eventually they put a label of it of chronic daily headaches, which is a catchall, but basically means I've had a headache since end of 2013, which occasionally flares up into full blown migraines. And when I say occasionally, I mean three or four times a month. That's it. That has been very formative in me building the businesses that I build. Initially during this time I built a consultancy of fractional CTOs. There were about 80 of us altogether, where I was essentially, I was reducing the amount of actual CTO work I was doing and focusing more on building a brand for this other group of people.

And that went quite well. And then eventually it morphed into what I'm doing now with CTO Craft. I found that a lot of the work I had done was actually more enjoyable because it was coaching people and supporting leaders rather than coming in to pick up the pieces after they'd finished or burnt out in a lot of cases. And so CTO Craft came from that, but it was also an opportunity for me to build something flexible, build something around my energy levels, the health problem, and that's where we are. And now I have an amazing team that I delegate quite a lot of stuff to, that means I have that flexibility while still being able to produce something of value.

I never thought that our conversation about fractional leadership would come from necessity rather than choice.

Right. Well originally it came from choice, but it became a necessity.

Are there any other gifts that your chronic health condition has given you, if at all possible?

That's a really good question. I think going back to what we were saying before about having to give myself a talking to, having to be a bit more mercenary with my energy levels and my time, I think that's a gift in a way. Because I think if I'd been at full capacity and had been taking on the same roles and same kind of projects, I probably would just be in a constant cycle of burning out, if I'm honest. I think being unwell has forced me not to do that in a way. Not that the opportunity hasn't been there and the opportunity is still there. Even running my own business, I could very easily pull myself into it and burn out again. But I think being ill necessitates being a bit more focused on how I expend my energy and the real return on investments and the real effects of going overboard and not succeeding. That's the only gift I can think of, otherwise it's a pain in the ass.

Or in the head. It's a constraint, and that constraint is often so telling and so teaching and there are other parts to our working life and our working choices that are immediately impacted by different types of constraint in really healthy ways. But I think hearing you talk about your own constraints is almost at the extreme there, that there aren't quite so many constraints that disable you from being able to fulfill your duties. Usually they're just really focusing in, and as you were talking there about, I was reflecting on my own experience and thinking, yes, how could I create these constraints in a positive way out of choice that weren't going to cause me the harm that you are experiencing, but instead can almost be positive ones that I put up deliberately.

Why do I need to wait until I get to a point where I have a real problem before I create those constraints? I wonder what opportunities I do have to create constraints proactively on under my own control.

That's a really interesting question. I think the first thing that springs to mind is that you would need pretty good willpower to impose some intrinsic constraints that you can actually benefit from. I suppose it comes down to stuff like habit building and goal setting. But I'd argue that having a rigid set of extrinsic constraints, it's not as romantic as you're making it sound. I think you do want to be able to flex on how you grow and on your habits and so on and so forth. There is such a thing as, what's it called? Ego depletion, I don't know if you've ever come across this term.

No.

Where you spend so much of your energy trying to reach targets or trying to diet or reach whatever goal you've set for yourself or so on and so forth, that you eventually just end up with no resources to actually accomplish that stuff. It's very commonly seen in people who set themselves too many goals or too many constraints.

It's ego depletion, so you deplete your ego as you go through that.

I think in order to meet a goal or in order to exact a small change in how you do things or how you see things or whatever, or to build a new habit, you do have to sacrifice part of your ego. That's essentially what you're doing. You are saying this part of my ego that is essentially drawn to eating pizzas at the weekend, I'm going to say, no more pizzas at the weekend. You are having to use energy to make that change and your ego is what pays the price. That's my understanding of it anyway. I might be completely wrong.

We see our ego as something negative there, whereas in fact you are giving it value.

Your ego is vital. Yes. Your ego is a hugely important part of how you grow as a human being.

Has it helped you?

It's made me value what I do more. It's made me value the people around me more. I think I congratulate myself probably rightly or wrongly in having such a great bunch of people that are around me. I can either say to myself, that's just happenstance and that's just the luck of the draw where I can say to myself, I have drawn nice people to me. I am partly responsible. And that feeds the ego. The ego feeds that back, as an example. But I think ego is vital. You can't go through life being completely subservient to others and ignorant of your own ability to make positive change. I think it's actually dangerous to do that, fundamentally.

It's bringing me back to that burnout death cycle. I'm imagining how that must have felt in that moment and how depleting it must have been, how it must have felt like everything was coming out of you and being given to everyone else. And whilst you are putting up the proverbial shit umbrella, it's all pouring. You are conscientious, it's seeping into you but not into others. And you're just constantly giving and being kind to yourself and recognizing the value of your ego, in some ways feels like a response to that in some way.

100%. You can't protect everyone from what's going on around you. You can't protect yourself from everything that's going on around you. I think part of it is just acceptance that you are still good despite that. We could get very metaphysical and Buddhist and everything, or suffering is important rather, and so on and so forth. But I think fundamentally it's just an acceptance that you are good, you are capable, you are loved despite all the stuff that you go through and despite all the stuff that you are having to deal with, that despite any mistakes that you make, that's important.

Do you ever get any of your clients balk at any of this?

Yeah, constantly. Constantly.

It's interesting just how through the course of our 50 minute conversation so far, we moved from the very practical to the very deep, so fast. But the two do feel quite close to each other somehow.

They are, yeah. I think it's about perspective and it's about willing to dig beyond the superficial. I think a lot of people who come our way, as I said before, the very common pattern is that people will reach the CTO level or the leadership level in general through being a very good individual contributor and being very good at fixing their own problems and or dare I say copying and past a solution from stack overflow, something like that. And then when you get to leadership, you can't do that. There's no copy and pasting. There's a different level of personal responsibility to the people that you're working with. I said yes very quickly to the question earlier on about whether people balk their stuff, and that's generally the first port-of-call that they haven't accepted that there's no single set of solutions to this kind of work.

There's no single approach to leading people and building a culture because a lot of it depends on you and your personality and your resilience and whether you want to be hands on or hands off, all sorts of different things. And people who come from a background of there being a solution to every problem, at least one solution to every problem, it can be difficult for them to understand that it's not just, right? Give me a playbook or give me a YouTube video I can watch that will give me the solution to this kind of problem. And especially where it's an issue within them that a lot of people hope that there will be a single thing that they can tweak in their life or a single set of actions they can take to overcome some very baked in feelings about how they work with people or how they interact with people, how they build cultures or build teams or whatever.

They do need to go off and do a bit more touchy feely stuff and get back into that understanding of where they've come from as an individual and what their hangups are. That could be difficult to stomach, especially first timers, that's very common.

And as you go through that, at every point you're always referencing that it's the individual that's the starting point, not you. That must be a common misconception because there must be a thought that, well if I go to Andy, I'm going to end up being a bit more like Andy. Whereas actually you are there to make them a bit more like themselves.

Exactly. That again is a very common misconception that they'll come hoping to learn from a guru who has all the answers and has done everything right throughout their career, or at least has made all the mistakes and there are no more mistakes to make and they've come out the other side so they must know well. But no coach is infinitely experienced in every single situation you might be in or so on and so forth. As I said before, I do take a lot of my own experience into how I coach people for sure. But I don't want everyone to be a carbon copy of how I do things, because it's not 100% right anyway. It's much more important that they become much more realized versions of themselves and much happier and more comfortable in what they do.

What role has privilege played in your search for work that's right for you?

I suppose in the early days, I think I built a pretty good network of people. I wasn't particularly privileged when I came out of university. I was same as everyone else. I'd say my parents were middle class, small holders in West Wales, I didn't really have much resource available to me other than a 56k modem when I was growing up. That was pretty much it. I didn't go to Cambridge, I didn't have a whole bunch of connections, I didn't have any money. I'd say in those early days, not a lot, but I didn't fight against not having that privilege either. I just did my thing and I built code and I got stuff done, essentially worked for some cool companies. But I'd say when I got to CTO level, I think I had a bit more privilege in my back pocket in that I'd made a lot of good connections. So my biggest, most powerful resource was the people that I knew.

I made connections with big VCs and I made connections with a couple of people who are running several companies who could be a bit of a lend in the ear if I had any questions about the business side of things. And then I also created a lot of privilege for myself. I created a situation where I could pick and choose the kind of work that I went for. I suppose that's it basically. But these days I'm incredibly privileged and I'd say the network that I have is still the biggest resource. I have a bit more financial stability and I have my family and so on and so forth, which are all massive privileges. But the value of the network that I've built as a professional is, that's the biggest thing that I fall back on the most as a professional person I guess.

Creating privilege isn't something that we talk a whole lot about. It feels more like actually we get given privilege, we have no choice about it. It's the conditions that are set that are outside of our control. But as you reflected on that there, it almost felt like at every point you're seeing privilege not as something that's outside of your control, but within it.

Well, to a point I'd say, and I think that's maybe a bit too blanket. But certainly I believe everyone's capable of creating, not creating their own luck, but certainly setting themselves up better to take advantage of luck or privilege, whatever you want to call that. I certainly have done entire projects or entire things to increase my visibility for example. I've done volunteer work to increase my sense of wellbeing and to scratch the altruistic itch so I don't have to bring it into work as much. I was very altruistic and so on when I started working. And that became an issue because I was doing too much basically. And so I created that opportunity for me to scratch that itch, to get that part of me that needed to be altruistic and charitable and so on into a separate part of my life so that I could do different things in a professional sense and be a bit more mercenary.

That's the kind of thing I'm thinking of. It's not that I created a big pot of money that I could have by the side so I could do anything I want or anything like that. It's more about taking advantage of situations to reduce the external constraints that I had on the way I was working and the work that I did.

It almost feels like the yin to your self-reflective yang. It's almost as if on the one hand we need to be able to constantly self-reflect and in order to understand our own inclinations and the directions that we want ahead in our own life and understanding ourselves more deeply really helps with that. But it's almost as if you can't do that in isolation. You have to do that in the context of a wider society. You need to experiment almost. You need experience the chance to be able to do different things. And somehow that conscientious and compassionate side that comes more naturally by the sound of things almost is complimented by this ability that you've built to be able to spot those opportunities and go after them, because ultimately we need both.

Absolutely. I think my ability to spot those opportunities and create that privilege for myself is a privilege in itself and not easily come by for sure. I think, especially if you are wrapped up in a huge amount of overhead with your work and your family and your social life and whatever else, it can be easy to miss opportunities to give yourself a bit of a cushion or give yourself a bit of a cheat code in a way.

When you reflect after all this, on what you choose to do with your working life, what are you optimizing for?

I'm optimizing for flexibility first and foremost. If I'm very honest right now, that's a necessity because of the health problems. It's not where I would like to be. I'd like to be in a position where I'm optimizing for helping as many people as possible, because that's my nature. Part of the mission of CTO Craft is to help more startups succeed by helping their CTO succeed. That's really what I'd like to be optimizing for. But fundamentally I think the path to reaching that end goal is going to be a bit longer because I have to optimize for flexibility and reduce the impact of me getting ill. That's where it is at the moment. Maybe it won't be there forever. Hopefully it won't be there forever. But that's it.

Andy, thank you so much for breaking down your story from the very beginning.

No problem. No, no. Good to talk to you.

All right, man.

Alrighty. Have a good afternoon.

Thanks. Bye.