how to make the most of the startup that is your life

over the past year or two, two books i’ve read have had a huge impact on how i’m running my life. the first is the lean startup by eric ries and the defining decade: why your twenties matter and how to make the most of them now by meg jay. 

what i’ve been doing is taking the build-measure-learn model from ries and using it in meg jay’s philosophy.

in the defining decade, jay discusses how most people are crippled by the inability to decide “what they want to do with their life.” this leads to them just doing whatever comes along (drifting) or, worse, actually making decisions that are counter to their well-being. 

to make matters worse, many people in my generation are taught (falsely) to believe that they can do anything. her antidote is basically a reality check. no one is actually able to do anything (and definitely not everything). in fact, if each of us took an honest look at our skillsets and our experiences, there are probably only 5-6 areas in which we could meaningfully work in a way that provides enough resources to live while also aligning with an interest or natural ability. 

this could be seen as limiting, but it’s actually quite freeing because it means you have somewhere to start.

so then the problem becomes how to figure out what to do from your list of realistic pathways. that’s where the build-measure-learn loop comes in.

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ries believes that successful startups in the long run aren’t the ones that execute brilliant ideas. he sees that success is determined by the ability to learn and implement lessons from that learning faster than anyone else in your space. that’s a bit of an oversimplification, but that definitely resonates with me. 

the trick, then, to figuring out what to do with your life is to set up as many ways as possible to learn. this thinking can apply to every area of life. work, love, family, place to live, etc.

part 2 coming soon: how iterating through the build-measure-learn loop helps you make more progress faster over time…

ps - i think ries pivoted away from the original build-measure-learn loop (above) to the one below. the original one is more relevant to this context.

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on the difference between projects and tasks

one part of the getting things done methodology that has been of critical value to me has been the distinction between projects and tasks. the distinction is subtle, but once you see it, you can’t unsee it. it’s totally changed how i see the world. it’s almost like a superhero power. at times it’s so helpful that it allows me to instantly predict whether or not something will be successful just by watching a few minutes of a meeting. 

ok so what’s the distinction?

there is lots of thinking about this and it can get a little circular but the simplest definitions i’ve found are this:

a task is a specific action that can’t meaningfully be broken down into smaller actions. a project is a group of tasks meant to achieve a certain, usually large, outcome.

so some examples to help illustrate (because it really is a subtle difference): buying a car is a project. the tasks associated with that project might researching what cars are in your price range, making a list of your friends who might sell you their car, deciding whether you will buy new or used.

another example (this example is dear to me because it’s the reason you’re able to read this piece of writing at all): starting a blog is a project. tasks under that for me were: picking a platform, creating a content creation plan, determining who my audience was (ended up using the audience of one strategy), and publishing my first post.

ok, so hopefully the distinction is starting to make a little sense.

now this distinction has helped me in two major ways. first, it helps me to break my projects down into pieces that i can prioritize in such a way that i know i’m being maximally productive while moving towards my life goals. second, it helps me keep my todo list uncluttered and flowing.

one of the most life-changing pieces of knowledge i took from getting things done is how todo lists end up blocking people from making meaningful progress in their lives. one pattern allen points out is that when your todo list equates projects and tasks, it blocks progress on the projects. that’s because the average person will always prefer to check off something that feels doable (watering the plants) over something that doesn’t (buying a car). this often results in easier things getting prioritized and leaves the really important stuff untouched… which, in the long run, undermines real progress.

shit. i’m over time. gotta run!

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designing "at" people is destined to fail

one of my favorite parts of the obsessed with design podcast, is the question about red flags. miles, the host, asks interviewees what signs they have learned to see that give them hints that their client might be a bad one.

mark palmer said that this is one of his red flags (paraphrasing):

“when people expect you to design at them, it’s a big red flag for me. when a client doesn’t believe that they need to be involved in the design process you don’t get buy-in. without buy-in, it’s much easier for a client to change their mind during the process without much reasoning. additionally, without client involvement, it almost always means the final design will be lacking critical information. good design must include those who want the design (usually clients) and those that the design is ultimately for (usually end-users).”

this resonates with me on so many levels. from a design standpoint, it’s unbelievably obvious when this is happening. when clients expect that design is going to be a silver bullet to their problems, their expectations often derail projects late in the process. when they haven’t been brought along, giving their thoughts and being a part (or at least informed of) major decisions, it’s super easy to say “hm. i don’t like that, but i’m not sure why. can you go back to an earlier stage and come up with some more ideas?” people usually won’t do that if they were a part of the decision. hopefully because they really incorporated their thinking at the decision point. but even if not for that reason, at least they won’t because they won’t want to contradict themselves.

from a process standpoint, this insight parallels the stakeholder engagement thinking in facilitative leadership methodology. the less you involve people the process that leads up to any decision, the more likely it is that they won’t be happy with or implement the outcome. as some of my colleagues used to always says “even if the decision was in their favor, if people don’t trust the process, they won’t like (and may even block) the outcome.”

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personal practice: being mentored and mentoring

the more people i meet, the more i realize that i have a set of practices that are really different from most. i’m not exactly sure why i’m like this nor do i ever want to boast about it. that said, when i share them, people tend to appreciate it. so here’s to sharing.

one of these practices is to always have a mentor and to always be a mentor.

i think this started in the tallahasee christian youth group scene. from a very young age i remember being in bible study groups taught by older people (mostly men). and then as i got older, i was tasked with teaching those same groups i had gone through. it started slow; sometimes when an established teacher was out, they’d ask one of the younger of us to step in. and then, over time, we got asked to lead/teach more regularly.

and then i realized there was a whole web outside of the formal structures (sunday school, bible studies, sunday night group). there were a set of older guys (roshad, ben k, stuart, the same crew from which i learned the importance of hugging) who had a cadre of guys that they mentored. it was always an honor (cool) to be close with (discipled by) one of those guys.

then, as the guys in my age group got older (especially once we got cars), we were encouraged to start and deepen those same types of relationships with guys younger than us. we would pick them up from school or give them rides to the church when their parents couldn’t or whatever. it really was a great time in my life.

the lessons i took away from that time are really what was important for me. and they are two-fold:

  1. being mentored helps you learn.

    having someone to talk to about life and give you advice as an amazing benefit (and as james altucher says, “advice is autobiography”). additionally, explaining what you’re going through helps you realize that you’re not the first to go through stuff. this had the simultaneous impact of making me realize that i wasn’t special but also that because i’m not special, neither are “they” (the cool kids/my role models), and i have the same potential to have impact as “they” did.

  2. being a mentor helps you see that you DO have experience, no matter how much you think you don’t.

    it adds validity to your experiences. being able to help someone else go through a difficult time based on lessons you’ve learned makes going through even the most terrible of situations feel valuable.

of course, finding people to mentor or be mentored by is a totally different topic (maybe for a future post). it’s also surprising over time how relationships shift with mentors and mentees (that, too, is maybe writing for a different post).

so yea. i genuinely believe that my practice being mentored and having mentors helps me have a perspective on life that keeps me grounded and needed. and given that i think we’ve forgotten how important it is to need and be needed, i think this practice will really help if adopted by more folks. it also adds connectivity to our societies and we need more of that, too.

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on specialization, expertise, and needing each other


“yes, i designed that thing in 30 seconds but it took me 30 years to get to the point where i could design that in 30 seconds.” - michael bierut (quoting paula scher) on design matters

as technology becomes increasingly democratized, some people have predicted the decline of expertise. some have gone so far as to advocate for it. they believe that the most successful people will be generalists (i’ll come back and find some sources for this someday).

i don’t buy it. at my last job, we believed strongly in this idea:

“do what you do best and connect to the rest.”

in effect, it’s a lean in to the idea of specialization. the paula scher quote explains why. over time, skills developed by individuals creates incredible efficiency gains. the same thing that may take an expert 30 seconds, may take a notive 30 hours.

and as i deepen my thinking (with ross) on snap and also personal branding, in order to build a world that works, two things are necessary:

  1. we need people who are going to be able to contribute effectively, and
  2. we are going to have to learn how to need each other in non-destructive, healthy, even generative ways.

of course, i don’t think that means people should (or would ever actually) be singularly skilled. but if someone has intentionally developed skills in specific areas, those should be capitalized upon.

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