Startup or Corporate: Which One is Right for Me?
Much like RF’s two roads in the yellow wood, contemplating whether or not to make the leap from the corporate sector to the startup sector can feel very speculative and unknowable. How different can those paths really be? A job is a job right? Either one and you got bosses, coworkers and other normal workday hassles right? 💯 So what’s the big deal? I mean, a startup is just a small company hoping to be in a big corporation right? Weeellllll, sure, but that doesn’t really paint the picture of day to day of getting there. This is a question I get often, and have coached many direct reports through during their first months of startup life (tbh, the topic is endless!) and below are my thoughts on the biggest differences that play out with real impact when making the transition.
At the end of the day startups are of course a part of the larger capitalist game we call the American economy, they just use different tactics to play the game and those different tactics can play out in big ways in the ‘office’ day to day, (as well as at home). The way I see it, the difference basically boils down to this: corporate employees are provided with what to do, when to do it and how to do it while startup employees are provided with logins and metrics to meet, expected to figure out what needs done, how to do it and then to go do it. If you are reading that and thinking, why would anyone want to do all that?!? You are not alone. But for many other folks (like the ‘crazy ones’ defined by Steve Jobs v 1.0, full quote below) that sounds like FUNNNNN. The difference here is just mindset, (and our own definitions of success), but wtf does that actually mean? Let’s break it down.
To set the stage, corporate America is something we all are familiar with: it was established long ago, there are established (or entrenched) ways of doing things, a structure with layers (who doesn’t love a good, dense bureaucracy shaping their day to day life), a business model that is taught in B school and is understood by most of us, a societal model of professionalism that is embedded in our American culture to name just a couple ways. And when you go to work in corporate America (TBH this tracks for government, education, non-profit and lots of other non-corporate organizations in America) you know what to expect from your employer - from new hire orientations and training manuals, from career paths and promotion tracks, to the gold watch at your retirement party in 20 years - and you know what is expected from you (I mean, in America we are pretty much trained for corporate life from ages 5-18+ in our school systems with set class times, right answers and clear paths through the hierarchy of learning, grades that progress in an orderly fashion to furnish you with clear skill development paths that build on one another, and eventually culminate in degrees before moving on to the next steps right?). With everyone’s expectations so well set, it’s hardly a surprise that as a corporate employee things feel comfortable and familiar, even safe and secure.
Startup America has lots of intersections with corporate America, but they can be hard to see off the jump due to all the divergences. Not to be confused with any old small business, startups are defined by the uniqueness of the product (often tech, but can be unique services or tech enabled inventions and services as well), and a desire to scale exponentially; and of course they use different tactics to play that game. It’s in those differences you will find a lot of divergences that can play out in big ways in the ‘office’ day to day, and most require a growth mindset that is not as familiar to most of us Americans. The following five divergences might give some deeper insight into what I mean.
1) Lifelong learning. In a startup everything is new….and to everyone in your company, not just you! And this is huge…it means all that stuff you are used to having handed to you in corporate settings are not available in a startup, and most likely there is noone there to teach you anything. (Seriously, no playbook aka job descriptions, ops manuals, training manuals, org charts et al, no precedent, and sometimes you even have to bring your own ball (yes, that can mean your own hardware, software, or even desk!)) Because the product is unique, (even brand new), and the leaders are unique and brand new, there is a lot being figured out every single day (yeah, ok, making it up as you go along definitely fits here), and you, the startup employee, have to be cool with all that. (Like really genuinely cool.) You have to like having to look up, dig deeper, and make decisions about all the unknown unknowns you encounter, and be excited about being the one to make your way through the chaos to cut a path for those who come after. As this can feel very confusing and uncomfortable, you need to embrace and love being a lifelong learner and learn to be comfortable being uncomfortable.
2) Team. The earlier you enter the lifecycle of a startup, the newer and less defined everything is. The founders (and other early employees) have taken the founders idea from inception to building and delivering a brand new service or product. They have grit (aka drive) and hustle (aka big capacity for getting shit done) and have spent their time using those two qualities to manifest this business out of their original idea. They probably have industry or product expertise but may or may not have any business or leadership experience, and this is their baby. These entrepreneurs are not the types to say “it’s just business”, and what happens at a startup is very personal, very intense and in many ways very intimate - as it must be if you are looking to change the world. So the team that surrounds the entrepreneur needs to get that…they need to be genuine, honest, flexible and willing to put their ideas and opinions out there. It is only with an ability to hear each other out even when they disagree that a team can achieve the gestalt which all championship teams have.
3) Strategic and Tactical thinking (simultaneously!). A startup employee can’t ever just focus on “their job”…they need to do their job with an understanding of how their contribution fits into a larger picture, and not just for today but also for where the company wants to be tomorrow. Remember, at a startup you are expected to jump in, ask questions and learn stuff to execute on what is asked of you, as speak up about things you notice need done, and you MUST speak up if you see something wrong because you are the only one who can. Seriously, as you encounter problems, at least half the time they have not come up before so you are gonna need to diagnose the problem, to come up with a solution or two and bring it to your boss, and then go implement those solutions…in hours or days, not weeks or months and it might not be the solution you will need next week when you hit another unknown unknown. Or not, maybe the problem shows that a tactic is not aligned with strategy at all! Even if you are an intrepid lifelong learner, comfortable speaking up, this constant onslaught of new things can take a minute to get used to (average ramp up time is a full six months, for both institutional knowledge needed to perform job and personal capacity to handle the environment and daily demands). The ability to understand the larger company goals and strategies is going to make prioritizing and executing your tactical day to day much more manageable, mentally at least.
4) Embracing Failure! (Wait, what? Why would anyone ever embrace failure, that is a 4 letter word in America!) As confusing as that seems on the face of it, think about it. You are doing something brand new, so even what you think you have figured out might be…wrong. 🥴 So your resilience in the face of failure has to be legit. I mean, if a problem arises, solutions are not in place that you can access, nor is there another department you can escalate to, (nor will your boss take the problem off your hands so you can focus on producing the widgets you are paid to produce, he’s got is own overloaded plate to deal with!) and while the lifelong learner is able to find a solution, is the solution you just put in place the right one? Maybe it fixes the issue but does not solve the problem. Are you sure the tool you chose up to 10x, 100x, 1000x the amount of work being done? Is there a more efficient way to execute your job? And on and on. Call it being willing to be wrong, a willingness to pivot or iterate, flexibility, resiliance or any one of a hundred other names…at the end of the day if what you did yesterday isn’t working today you gotta be willing to face it, embrace it and try again.
And all of this new office day to day means what to your personal life?
That brings us to 5) New work/life balance. Just because you work for a startup now you still get to go home at the end of the day right? Yup, for sure…but at a startup you are going to need to be super conscious of the fact that it’s a marathon, not a sprint. Being part of a mission that you believe in (especially one that will change the world) makes it easy to give up the 9-5 boundaries of many corporate jobs, but how do you keep that from going too far? It is easy to get sucked into a constant sprint, working as hard as you can for as many hours as you can week after week. Startups give you a lot of work, a lot of agency to execute that work in the way that you think is best (as long as the deliverables achieve company goals), and very little guidance in how to accomplish and manage all of that…so yer gonna need to bring your own boundaries to be able to balance that. Here again, your personal mindset comes in. You have to know what you need for self care to balance the sometimes grueling workload…and learn to recognize the signs when that balance gets out of whack. You have to set your own boundaries for how much you can do, how much of your time you are willing to be available (even when you are not working). No decent founder expects you to work as hard as they do, but they will let you work yourself 24/7 if that’s what you want, so finding your balance is up to you alone.
If you’ve gotten this far, you might be questioning the sanity of startup life more than when you started. (And I can tell you many of my family and friends have certainly questioned mine, the question “why don’t you just get a job? being one that I and every startup lifer has heard). I can’t tell you what you should do. All I can tell you is that as a chronically underpaid early stage startup leader (I never got paid what Google said I should), I always had lots of options and loved the idea that the better I did my job, the more those options would be worth some day…it makes my contributions feel more real and impactful. And if the options don’t end up being worth much, at least I got to try out my own ideas, own my own time, be a part of (and even lead) some incredible teams and find a comfort and freedom I never knew before joining a startup called G5 in 2008. ‘Crazy’ or not, a successful startup employee requires a personal mindset that is different from the mindset needed to thrive in traditional corporate environments. I hope this basic breakdown helps you find some of the clarity you need to decide your path. (And if you want a bit more, there is a baseball/rubgy analogy below that might resonate).
Peace and Love.
May 2023
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“Here’s to the crazy ones. The misfits. The rebels. The trouble-makers. The round pegs in the square holes. The ones who see things differently. They’re not fond of rules, and they have no respect for the status-quo. You can quote them, disagree with them, glorify, or vilify them. But the only thing you can’t do is ignore them. Because they change things. They push the human race forward. And while some may see them as the crazy ones, we see genius. Because the people who are crazy enough to think they can change the world, are the ones who do.” ~ Steve Jobs, circa 1997