Making Deliberate Decisions about the Evolution of My Career

A Seven Year Retrospective and Looking Ahead to What’s Next

I recently celebrated my seventh anniversary at The Ready. I’ve been involved with basically every aspect of our business (being the first employee means you kind of don’t have a choice but to wear a lot of hats) but the vast majority of that time has been spent as what we call a “Transformer” — an organizational transformation consultant working day-to-day with our clients. This has spanned countless standalone workshops, many light touch advisories, and several intense and deeply involved long-term transformation projects. This means I’ve spent much of my time as a member of a client-facing duo, a lot of it has been in solo engagements, and some of it has been as a leader or member of a larger team. I’ve done a lot, learned a lot, experienced the depths of burnout, the highs of full engagement, and basically the entire gamut in between (fortunately, with a definite weighting toward the positive end).

Anniversaries are a natural time to be reflective so I’m going to use this writing exercise as a way to figure out what I believe about my career path and also as a model for how you can think about your own career evolution. I believe I have control over the majority of the decisions that create the life I’m living and career I’m building. Since I believe that, it’s imperative I check-in with myself from time to time about how things are going, where I think I want to go next, and what I might want to try in the future.

Instead of taking each of those questions in turn, I’m going to instead look at what I think the “adjacent possible” looks like for me with where I’m currently at in my career. Across each of these scenarios, I’m going to ask myself:

1. What emotions come up when I envision myself in this future?
2. What would I miss about this option if I don’t choose it?
3. What pushes me away from choosing this option?

Scenario 1: Keep on Keeping On at The Ready

The obvious option is to keep doing what I’m doing at The Ready. I don’t know how else to really say that what I do at The Ready, in almost every aspect, is my dream job. We exist to change how the world works and we use ourselves as the first and best test environment for a better future of work. Fully self-managing, self-set compensation, fully distributed, great benefits, three times per year in-person retreats in excellent locations, crazy access to well-known clients who trust us to work on gnarly problems… it really doesn’t get much better for consultants.

The emotions that swirl around inside me when I think about another seven years at The Ready are primarily safety and familiarity. It’s what I know and I think I’ve developed legitimate skills that make me desirable as a partner to my colleagues and my clients. That’s not to say that I have universally positive reactions to these quite positive feelings. I’ve come to mostly distrust feelings of comfort and familiarity when it comes to career growth. Most of the best things that have happened to me regarding my career have been the result of stepping into the unknown and taking risks — leaving my teaching career to go to graduate school and then dropping out of my PhD program to move across the country to join The Ready are the two biggest examples that have worked out incredibly well.

As I write this, I’m realizing that the fact that I think I always need to be doing something scary and unknown in order to feel like I’m doing the “right” thing in my career is probably a fruitful topic of conversation to have with a therapist and not something I should just accept as right. Nonetheless, I’m going to feel my feelings and say that the fact that The Ready feels like the safe option puts me a little bit on edge.

If I were to move away from The Ready I would inevitably miss some of the things that makes this my dream job. I can’t think of any other organization where I’d have as much freedom and as little oversight as I do at The Ready. The only way I could get more of these things is if I worked completely for myself. Even then, it wouldn’t be that big of a change to my day-to-day work.

If I’m being honest with myself, I know I’d miss the steady paycheck, too. It’s not sexy to say, but my paycheck is a huge part of why I’ve never even considered something other than The Ready. We are well-paid for what we do, especially for early to mid-career consultants. I think I see a bit of an earnings ceiling given our current financial system, but I’m not in risk of bumping up against it anytime soon.

Finally, obviously, I’d miss many of the folks who I’ve come to call dear friends. We’ve grown beyond the point where I have a personal relationship with everyone who works at The Ready, but some of my best friends are colleagues I met at The Ready. The overall calibre of person we attract and the hiring process they have to go through means I’m surrounded by nearly universally stellar folks.

As I already mentioned, I’m inherently skeptical of anything that feels like the obvious or easy answer. Beyond that, though, are there other things that are pushing me from sticking with this scenario? On good days, this work feels radically impactful and meaningful. On bad days or weeks, though, it feels frustratingly ephemeral and hit-or-miss. If things aren’t catching on at the client, if the bureaucracy is too resistant to our efforts, or if the myriad of other petty frustrations that emerge when doing client-facing work or while operating in a self-managing organization start to pile up, then I can feel my energy and motivation to do this work dissipating. Is it worse than the frustrations that come with any job? Unlikely. Do they exist? Absolutely.

Beyond the petty frustrations, organizational change work can be truly emotionally draining, too. Most days are marked by high intensity human-to-human interaction — whether internal team meetings to figure out and prepare for upcoming moments with the client, client meetings where we’re facilitating or otherwise in charge of the design and flow of a high stakes meeting, or hours or even days long workshops where we’ve often designed, from scratch, multiple high impact and contentious conversations and activities for some of the most demanding and difficult people on the planet — senior executives. I’m good at all of these things, but they come at a cost. I’m an introvert at heart and while I can turn on my extroversion to facilitate a workshop or a meeting, it feels like I need more and more time in between these moments to fully recharge my introvert batteries. If I had my druthers, I’d spend 80% less client-facing time than I currently do.

Scenario 2: Internal Leadership Role Elsewhere

I’ve always felt a tinge of imposter syndrome for having never worked in a large bureaucracy like the ones I consult with everyday (other than my extremely brief foray in the American public school system as a teacher). Would I be able to bring the type of change The Ready is hired to bring if I were a leader in a “regular” organization? Would I fall prey to the same things I see the leaders I work with fall prey to? Would the toolset I’ve developed at The Ready serve me well if I had to operate from the inside? I don’t know — and part of me is curious to find out.

This scenario would entail getting hired as a leader at an organization doing something other than what The Ready currently does. It could be a big name organization or it could be something smaller. In either case, it would be more about the role and whether it has enough positional power to actually let me bring interesting and worthwhile changes to a meaningful segment of the organization.

When I check in with the feelings that come up when thinking about the future where this is what I’m doing, I predominantly feel fear, apprehension, and excitement. Like with the feelings that came up in the first scenario, I don’t necessary view these as negative (at least the fear and apprehension aspect of it). I’ve done great things in my career and life when I’ve felt fear and apprehension — but did it anyway. Might that be the case here?

If I didn’t choose this option I think it would feel a little bit like I’ll never know if I can actually truly walk the talk of the org change and org design stuff we talk about at The Ready. I will never know deep in my bones what it is like to work for a broken bureaucracy (yes, I know how weird it sounds to put this down as something I might have to give up if I never pursue this option).

I also wonder if not going down this path means I won’t be able to open a level of compensation that may be beyond anything The Ready would ever be able to pay me. As I mentioned in the first scenario, I’m nowhere near that hypothetical earning ceiling yet, so this is a truly hypothetical situation that wouldn’t come into play any time in the next 5–7 years.

As far as what pushes me away from this option, there’s almost more than I can feasibly list. First, I know I would hate the lack of autonomy. I don’t have a boss at The Ready and any organization who would hire me would inevitably put me into some kind of organizational structure where someone is my boss. I hope I would learn to operate in that environment, but I know I’m dispositionally disinclined to work well in a highly hierarchical environment. In a similar vein, although I’m interested in bureaucracy from an intellectual and theoretical standpoint, I know that working in one day after day would wear me down to a nub quickly. As an external consultant I’m able to retreat from the client’s bureaucracy into the warm embrace of The Ready when it all becomes too much. That isn’t an option when that bureaucracy is your one and only work home.

Lastly, I can’t actually see myself being qualified for many, if any, senior leadership jobs at non-consulting organizations. At least, I’m not an obvious fit. I didn’t go to business school and I don’t have the bureaucratic experience I suspect you need to even stay afloat in many organization like that. I’m not sure how much seven years at a totally weirdo of a self-managing organization translates into the world of “regular” organizations. I don’t think I could be a Chief People Officer without any real HR experience. Chief Operating Officer? Maybe, but unlikely. CEO? Maybe in the right situation. The only obvious one would be some kind of Chief Transformation Officer but even that seemingly perfect job title often means something quite different than how we think about transformation at The Ready.

Ultimately, I don’t think this is a scenario I really need to think about because I’m not inclined to spend any effort making it happen. If something interesting were to fall into my lap by way of a friend, acquaintance, or recruiter then I would at least take a look at it. Even then, my criteria for whether it would be worth making the jump would be incredibly stringent. But everyone has their price, right?

Scenario 3: The Indie Shift

I always assumed I’d be an indie of some sort. When I started making money from my first website in 2009, I figured I’d be doing some version of that for the rest of my life. Even after going to graduate school, I figured I’d have some kind of solo coaching/consulting/writing endeavor that would form the cornerstone of my career. It was while I was studying independent work as a research project that I became aware of holacracy, sociocracy, and other fascinating organizational theories. Once I found The Ready, I put the dreams of an independent career on the shelf so I could focus as much as possible on building this company. Even while pouring myself into The Ready, though, I’ve always kept one foot in the indie world by writing as much as I can, particularly through my The Deliberate newsletter. Sometimes I catch myself thinking and feeling that The Ready is still just a detour from the indie career I’m supposed to be creating for myself.

The emotions that come up when I think about having successfully shifted to this scenario are pride, authenticity, and excitement. The emotions that come up when I think about the process of shifting in this direction are dread, fear, and anxiety.

If I never end up doing this, it somehow feels like I’ll be neglecting a part of me that has been a large part of my identity for a long time (even while working full-time for an organization for the past seven years). It feels like I would miss out on the best opportunity to ever craft a work situation for myself where I would truly have full control over my time. I’m pretty sure I’ll always think about what I could have done as an indie and regret never taking a true crack at it.

That being said, it would be unequivocally stupid for me to shift hard into an indie career at this moment. The Ready already gives me almost complete control over how I spend my time so I’m not really sure my day-to-day working life would actually look much different if I was “working for myself.” I’d be doing largely the same work without the nice paycheck, nice colleagues, or any of the other world-class support that you get when working for The Ready. What’s the point?

The fact that I haven’t made major strides in this direction, even while holding down a demanding day job, also makes me think that it would be foolish to make any drastic decisions in this direction. I’ve definitely read stories of people who drew a line in the sand and said, “After this day I’m 100% indie and I have no choice but to figure it out.” I admire that, but I don’t think that’s for me right now. I’m still supporting my wife through the last part of her graduate school work, we are thinking about starting a family soon, and we both have enormous student loan bills that need paying. Doing anything to radically negatively affect my income in this moment is a non-starter.

That being said, this strikes me as the type of thing that can be built slowly over time until the shift to it becomes the obvious thing to do (if I want to) rather than needing some kind of leap of faith. The delicate balance I need to walk, though, is figuring out how to keep chipping away at the work that lays the foundation for this at some point in the future without letting it either a.) distract me from work at The Ready or b.) make me feel like I’m continuously failing by not doing enough. The latter of these two options has been a historically difficult path for me to navigate.

Scenario 4: The Wildcard

Must my career continue down the organizational consultant/coach route? All three scenarios above are basically just reformulations on the same raw ingredients (with maybe a bit more ambiguity in the actual work to be done in Scenario 3). Should I be casting my net wider, though?

A major mid-career shift would need to have some extremely excellent reasons for making it. Since I already love what I do, it’s not about escaping something that is destroying my soul. It wouldn’t even be about increasing compensation as I’m already well compensated in my current line of work and there’s still ample room to grow, if I want it. Instead, it would have to be about avoiding some kind of inevitable AI/automation related redundancy or simply the desire to do something different.

I don’t think what we do at The Ready is at threat for any kind of imminent destruction by AI. If there are ever organizations comprised of people then there will be organizations who can benefit from the expertise that we bring (I think). Then again, how many people predicted that illustrators would be at the verge of being replaced by AI before the recent explosion of DALL-E and the other AI image generators of the past few months?

If I wanted to absolutely future proof my ability to make a living, what would I do? I think it would be re-training as a software engineer. I’ve always been deeply interested in tech at least from a culture and philosophy standpoint. I’ve always liked the idea of creating software and have made a couple half-hearted attempts at teaching myself the basics. I definitely have some internal scripts telling me that I don’t have the mind or ability to learn to code, but there’s very little evidence from my life that validates those ideas. It would be hard as shit and probably very frustrating, but I’ve shown myself that I can learn anything I put my mind to needing to learn. Is that what I should be doing here?

(There’s an interesting digression I could go on here about how the best way to future-proof my career from AI obsolescence would be to double down on the only thing that AI is never going to be able to replace — me — which means Scenario 3 , not learning to write software, is actually the most future-proofed path forward.)

A Third Way Emerges

Obviously, there are options outside of the four I just described and as we like to teach our clients, there’s almost never a simple binary decision to be made. There’s always a third way. What’s the third way between, or mixing, these scenarios?

I probably should’ve led with this in case any of my colleagues at The Ready have been reading this article with increasing levels of concern; I’m not leaving The Ready. However, I think there are things that each of the scenarios I described above that are worth trying to incorporate into how I craft my roles at The Ready to make my work more sustainable, enjoyable, and impactful. For example, I’m going to continue looking for opportunities to architect and advise projects rather than spending all my time in the day-to-day client work. As I continue to develop expertise in this work I want to find ways to leverage this hard won experience into ways that are more valuable to The Ready and more interesting and engaging for me.

This also means leaning into the opportunities to direct the entrepreneurial energies I described in Scenario 3 into new opportunities at The Ready. We’ve never conceptualized our work as solely delivering consulting services. We’re actively experimenting with products, new services, and other variations on our tried-and-true approaches. The recent work we’ve undertaken in the DAO/web3 space is a great example of this. It has helped me better understand what I’m good at and what I like doing. I like being on the cutting edge of figuring out what’s possible in a new space. The first couple years at The Ready, specifically the first few months where the team was extremely small, was an absolute peak experience for me. The DAO/web3 work has reminded me that this is where I tend to be at my best. Where else can I do that at The Ready?

Just because I’m not planning on leaving The Ready any time soon doesn’t mean that I can’t keep developing my own personal brand through writing online. I know that when I’m writing regularly I feel the best about myself across almost all aspects of my life. I’ve played with the causality of that relationship and I’m 95% sure that writing is actually the cause of those good feelings, not the result. Writing at SamSpurlin.com and for The Deliberate needs to continue being something I do more regularly than I have been recently. These may become the kernel of an indie career some day and they may not. Nonetheless, I need these outlets in my life for my own psychological health, if anything else.

Scenario 2 is the one that feels most unknown and the one that I should be most careful writing about in absolutes. What I can say about moving to any kind of internal role at a non-consulting company is that this is not something I am ever going to actively search for. But I would be disingenuous if I said that I wouldn’t leave the door open for surprising opportunities. If a former client, friend, or acquaintance thinks I’d be the right fit for an interesting internal role I’d take a good long look at it even though my situation at The Ready is already as ideal as I can really imagine a job getting.

Somehow, it feels like I’m “cheating” on The Ready by even saying it, but I think it’s worth saying it out loud. The decision to keep doing what I’m doing should be exactly that, a decision. And not just a decision I made once a long time ago when I was in a different phase of life, but a decision that I revisit and re-confirm regularly. Inertia is a scary force. If I’m going to stay at The Ready I want it to be a conscious decision with real trade-offs, not just the thing I do because it’s the only thing I know. I welcome the opportunity to regularly look at my decision to remain at The Ready, hold it up against something truly compelling, and (likely) choose to keep doing it. It feels like the only healthy way to stay at one organization for a significant amount of time and not become complacent.

You’ll notice that I didn’t spend any time laying out a grand unified vision for the evolution of my career. I did that once. Nothing I currently do was part of that vision, and yet, as I’ve said many times throughout this article, I love what I do right now. I’m much more interested in looking at the adjacent possible and figuring out how to consistently attain that, rather than following any sort of master plan. As long as I’m consistently feeling like I’m stepping toward the unknown, making a real impact with the work I’m choosing to do, and feeling like I’m building mastery I think I can’t be too far from where I need to be.

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