Chaos Muppet Strategic Planning

A Guide for Plotting the Rest of Your Life, Terrifying Your Neighbors


I’ve spent the past few months in this exceptionally weird, expansive state of nondecision. There’s a scene in the last episode of the West Wing – someone’s trying to decide what to do after the administration ends – and the resident curmudgeon replies: “You’re a woman with a lot of options and you’re acting like the world is backing you into a corner. Maybe you should stop bouncing, pick something.” Ugh. Exactly. I’ve watched it a billion times and yet still couldn’t manage to pick a thing. (For what it’s worth, the way I feel about jobs has helped me understand how the rest of you feel about Tinder.)

Talking and kvetching about, I’ve gotten the sense that this is everything-is-possible paralysis runs particularly rampant in early-career global health and development circles for a few reasons:

  1. People tend to be drawn to this realm out of a compulsion to address particular problems, but when it comes to translating that into a functional career, there are fifty different ways to work on the same thing. (You come out of an internship in undergrad struck by the problem of antimicrobial resistance, say – but do you work on drug pricing? Pharmaceutical incentives? Behavioral research? Medical research? An intervention-based startup to improve compliance? Russian prison reform?)
  2. This space is also overwhelmingly interdisciplinary (epidemiology bleeds into biosecurity which bleeds into soft power and regional dynamics, which bleed into U.S. foreign policy…and that’s just my weird corner). In my experience and perhaps in contrast to other arenas, this actually gets worse with research-oriented graduate education.
  3. There’s also the problem of a hiring bubble: students emerge from MPHs & similar programs with concrete experience and hard research skills, feeling capable of doing a lot but mismatched to market dynamics or otherwise priced out (expected to intern after a master’s, etc).

I’ve also been getting a lot of emails asking for general career advice lately (which I am still totally happy to answer, eventually). But when wait-I-need-a-job season started in full force around February I had no idea what I was doing & so felt like the falsest prophet. Once I figured that out, the process I came up with was so clarifying that I thought a generic guide would be a useful standing resource.

big picture glance.jpg
Buckle up.

While I’m sure you can do all of this on your own, I think it’s best accomplished in tandem with someone 1) who knows you well and is both 2) is reasonably familiar with your field and 3) in a similar job-life situation, with whom you share a 4) mutual respect for judgment. (I think this could work with someone 3-5 years ahead, too, but it requires such a substantial time investment that that person has to REALLY like you.)

My friend Christina and I are very unintentionally The Same in both boats and life stages, and close enough in skills, personal preferences, and goals to mutually understand one another, so this worked out really well. The last time I was in North Carolina we set out once-and-for-all to spend a full day on a grand “what the flip are we doing” adventure with the added benefit of her excellent porch. (Did I mention she’s flying to Dar today? And I’m off to N’Djamena next week? Might need to add a warning label…)

I’ll provide some of my examples along the way to the extent that they might be instructive rather than constrictive, albeit with strategic obfuscation, and primarily pictorially so as not to interrupt the process narrative. A few of our other friends came around to gawk/test it out with their lives, so those might pop up too.

Note: This is not necessarily an entry-level activity. You’ll need to have some vague idea of some problems you’d like to spend your time working on, as well as some familiarity with people who work on them, employers that pay people to address them, and powers that be that dictate the rules of the game. While I think the process is probably transferable to a huge variety of jobs and plans, it’s best suited to someone in transition: leaving or considering a degree program, transitioning out of the military, working in an interdisciplinary realm or an industry in transition, or perpetually panged with early-career twentysomething “what is my life” angst.

(A note on naming, for the uninitiated: muppet theory is a critical sociocultural framework. If you’re an order muppet, you’ve likely already selected a career with a clear structural path; barring that, you probably integrate regular process updates every morning by virtue of immaculate mental organization, and never would have let it get this bad in the first place.)


  • I recommend physical over digital planning for the sake of focus, color-coding, and rearrangement.
  • All of this was heartily assisted by mental lubrication. Research shows that a BAC of ~0.07 reduces anchoring while enhancing creativity, and so I suggest hovering around two-beers-in equilibrium (this took us 14 hours; plan accordingly).
  • Stewing is helpful. I had planned to do this for at least two months before I actually did, so there were lots of vague ideas floating around waiting to be organized. In fact, I think this sort of in-depth reflection is done best removed a bit from things: a time when and place where your brain has shed the burden of managing the complexities of being in the weeds, zoomed out enough from the dots that they might form more than one emergent constellation.


You’ll need:

  • Paper and tape
  • Sharpies, multiple colors
  • A big wall
  • Munitions, ideally low-ABV and high-carbohydrate
  • A good chunk of time


Process Dumb
All right, yes, we planned the whole planning thing backwards…
  1. Identify hard constraints & defining frameworks
  2. Brainstorm, specifically
  3. Break for extracurriculars
  4. Cull options from brainstorm
  5. Paradox-of-choice the options
  6. Back-project value added
  7. Forward-project future options
  8. Pro/con your immediate options

Step 1: Hard Constraints

North Carolina in March is plagued with inchworms. Everyone working in a 20160403_130610bio-related field is allowed to have one thing that squirms them out irrationally, beyond measure; these guys are mine. They therefore became symbolic of negative constraints: strategic-level things you absolutely don’t want, no matter what. We were both feeling simultaneously super quagmired and overwhelmed with options. Big process goals were obvious: don’t end up pigeonholed, avoid stalling further, and avoid purely theoretical conclusions (so, come out with a concrete plan of action). There are a whole bunch other practical things here that aren’t written down: the need to be able to pay rent, student loans, etc.

Positive constraints are a little more amorphous: they exist in some Neverland universe of possibility, dependent upon a whole bunch of other things. 10 years out seems like a good timeframe for “yes, I’d definitely like to do xyz by this time” projections: far enough away for steering room, and yet close enough for cognizant structuring. (While 35 makes me unspeakably nervous I feel less so when I think about being 15, so this was doable.)

It’s also important to understand how you Hard constraints positivemight select between these things, should any of them come into conflict (per my eternal fave, Bob Shacochis: “You always know better, until suddenly you don’t seem to know anything at all”). This is one of those arenas where the “three options, pick two” rule comes in handy. And where a framework is useful, but where flexibility might be called upon for a whole variety of reasons.

Step 2: Targeted Brainstorm

The goal here is to generate options, without throwing things out immediately for seeming irrelevant or unfeasible. But this is a specific brainstorm rather than a normal brainstorm because the Curse of the Ambitious Millennial a state of floundering paralysis derived from feeling as though one has too many options, wanting to do too many things. Try, very hard, to limit yourself to FIVE THINGS for each of the following:

  1. Problems
  2. Where
  3. [Majorsuper]Talents
  4. Time/when
  5. Skills needed
  6. Nevers

What problems do you want to solve?

This is the hardest part. It’s the main thing you’ll want to circle back to at the end, cross-checking your decisions.

What problems do you solve? What questions do you want to answer? It’s very important to differentiate this from what you want to be. (I’m reminded of F. Scott’s letter to his daughter: “Don’t worry about triumph. Don’t worry about failure unless it comes through your own fault.”)

We both ended up going on long, impassioned rants articulating semi-specific, north-star sorts of Big Problems that could nevertheless be addressed via a variety of paths. Christina knocked hers out right away (see: that mess of a

xtina big goal
Anyone’s guess, really.

photo). I think I’ve subjected fiveish people to
mine at one point or another, plus or minus all of Xtina’s neighbors; it involves a big rant about Osama Bin Laden and is equally unintelligible without going through the whole shebang. A North Star isn’t necessary, strictly speaking (they usually emerge with experience, in a lightning-strikes sort of congealed epiphany) but you should be able to come up with 4-6 things that really drive you: things you’d willingly stay up all night working on, for which you’d sacrifice some creature comforts.

Once you’ve got a list, you need to articulate and justify them to another party – who should be listening critically. Are you making any sense? Are you phrasing the thing in the best way possible? Are you going in with assumptions that don’t necessarily hold? When they’ve been hammered out and clarified, they should be messy, edited, clarified (see below).


Where could (and would) you feasibly live if you were going to address those problems? If you’re in the U.S., what cities are hubs for tackling them? If they’re international in scope, think about what regions/countries you might want to live in to gain experience tackling those problems, or the exposure you need to solve them. If you’re picky, note it; if you’re not, don’t. These should all be hard yeses under the right circumstances – places you would not hesitate to move to or work in.

We found it useful to add in secondary options for location. These might fit, but seem less likely or be less than ideal for some other reason, or require some particular constraint. (In my head these are the “would definitely move here for non-job reasons and make the rest work“ cities.)


In a group of smart people with similar certifications, what roles do you default to? What tasks jive irrevocably with the electric makeup of your cerebral cortex? These should be functional and strategic – focused on roles and processes at the root of particular tasks – and if possible, you want to distinguish these from elements specific to your field and training.


This one is tricky, but important. I’ll go heavy on the examples.


  • If you want to do a bunch of different things, and serve in a bunch of different roles, do you have to do them in a particular order for some reason or another? If you want to jump quickly up the GS scale, it might serve that interest to enter public service via a PMF fellowship after earning a master’s degree. If every job posting that calls your name concludes with “master’s preferred,” do you want to get that out of the way first or (global health folks considering MPH/MA/MPP/MScs: here).
  • Some career paths require, more than others, a steady procession through roles of increasing responsibility, with regimented procedures for advancement (medical/legal/military work obviously, intelligence, Hill stuff).


  • Hard constraints. For example, subject to all the caveats that accompany 10-year projections: if I want to have kids before risking all the fertility age stuff, that means I have to be in a relationship for multiple years before that, and know the person for a while before that, all of which for me probably requires some semblance of stable geographic propinquity – meaning I have 5-6 more years at MOST to accept long-ish and irregular international postings.
  • Powers That Be. If you’re a Democrat who wants to serve in the executive branch, but come November we’re slated for President Cruz, you need to figure out what to do when your party is not in power to make that a semi-feasible option down the line under President O’Rourke in 2024 (is that career agency work? State government/Congress? Academia? Private sector? Any/all of the above?)
  • Structured luck. Every path has its inflection points – right place, right person, right time. This is distinct from luck in that it entails precise preparation: you need to identify what levers you want to push, develop a strong gut instinct for vetting those opportunities in advance, and be ready to jump when they arise. You can’t make lightning strike, but you can forge yourself into a conduit.

Skills Needed

Look at everything you’ve written down and come up with a list of general requirements – most will be gaps from where you are now – reflecting every dimension of human capital you can think of that might be of use what you’ve thrown together so far. There’s the resume stuff (degrees? language skills? international experience?) and the je ne sais quoi semi-tangibles (buy-in from certain parties? contacts in certain places? group/title-based social vetting? battle-hardened psychological rigor?).


It’s just as important to have a list of things you don’t want to do, ever. These will pop up as you proceed through each brainstorming category, and you’re going to love them because they will help you target potential options, cut off paths, and save you from pursuing dead ends. Examples: I definitely do not ever want to live in Atlanta (why did I fill out a bunch of USAJOBS apps for entry-level CDC positions, then? no idea). I found a comms-oriented position I thought I could score at an organization I’d love to work for, but I’d go insane if I were pigeonholed into comms. I’d rather work somewhere where I have to accept limited influence over tangible impacts than somewhere focused on purity of principle with no promise of implementation or targeted dissemination.

(Anonymous medschool friend showed up! We made her try things out with that framework in mind. I think it worked well.)

nevers all three

Step 3: Extracurriculars

Break time! What fun stuff do you want to do that isn’t necessarily tethered to a job? (This is where we got lost in like a 20 min discussion about how badass Krav Maga is so we all put it on our lists, not sure whether that’s real or not…). Go big or go home. My weird impossible extracurricular dream (maternity leave? retirement?) is to operate an artisan b&b in the Shenandoah foothills, serving TexMex/Levantine fusion, that also moonlights as a low-profile Camp David. Never gonna happen. Whatever. Write it down.

Keep these in mind later on when you’re picking parsing or ordering particular options! I really want to learn to sail but no way I’m doing that in N’Djamena. I had wanted to volunteer semi-heavily before the election; irrelevant abroad, and less impactful if I worked in D.C. over North Carolina. I don’t want to work as an engineer but I miss making things and so I’ve gone down this weird “how do fire sculptures work and when I own a Victorian mansion can I build flaming gryphons to flank my entryway?” path (again, probably not ideal for DC or anywhere abroad…). Medschool friend wants to read a book a month and I totally believe in her.

Step 4: Cull Particular Options

Right. Now you’ve got roughly 3,000 paths to maneuver, rather than infinity. We’re getting somewhere. Which fit together into coherent arcs?

Some research will be critical here. LinkedIn stalk. Google relentlessly. Download obscure reports. Pick some crazy dream jobs, break down the requirements into bite-sized pieces, and map them on to what you’ve got. Figure out who the champions are; become familiar enough with the landscape to parse groups who employ the same buzzwords in support of different underlying philosophies.

The most important thing is to come up with a set of options for what to do next. I’ve found that three is a good number: enough to feel satisfied, few enough to hold the differences in your mind. Ping-ponging is okay – expected, really!, it’s almost weird if you don’t – and you’re going to iterate as you learn. But six months of paralysis will make you crazy and worse off than before. Six months in something you feel is off might place you in the wrong silo. In the global health/dev world, that’s a little hard to escape from (excepting functional roles: comms, m&e) because the market is so saturated (want an entry-level WASH internship? you WILL have competition from someone who spent 4 years working on the EXACT project). Also, be diligent about finding and making room for middle ground. There is almost always a way to shuffle activities around your day job such that they better position you for a bit of a jump in the future.

Step 5: Paradox-of-Choice (v) Your Options

Confession: I haven’t actually read this book (as a Duke grad I’d be remiss if I didn’t stick more closely to Dan Ariely…) but the wiki article is the first thing that pops up when you google “overwhelmed by too many choices”, and I found it useful, so here we are. Do you want things for reasons that are internally inconsistent? Are you relying too much on conclusions from past experiences that may no hold hold water? Pick out why you believe what you believe about the right path: anecdotal evidence? Expert advice? Again, cross-reference your hard constraints.

This is where your partner is going to come especially in handy, and where it’s most important to make sure you’re talking this through with someone willing to poke holes in your reasoning. Christina was maybe a little too focused on sticking around Durham, to the extent that she was applying for a whole bunch of things on her nevers list. I was too stuck on staying in DC for dumb reasons. Medschool friend probably needs a specific person to be her research mentor/champion but was holding back because there a billion other things to do.

Step 6: Back-project value added

Figure out how long you’d be pursuing each option (be they jobs, degree programs, fellowships, internships, whatever). At the conclusion of each, what will you have gained?The “skills needed” brainstorm list will be most useful here, but each opportunity probably provides other perks as well, and make sure to add those too. Some options might emerge as more efficient than others (same skills/credentials gained, less time); sometimes you want to deliberately favor depth over breadth.

Step 7: Forward-project future options

It’s 2 years down the line. You’ve received an MBA, your brain thinks Cyrillic is normal, and you could sleepwalk your way through an argument about human rights in Nagorno-Karabakh. From the perspective of the framework you’ve already established: what’s next, 2.0? Are any paths clearly cut off? Have you specialized to your benefit or detriment? You’ll want to do this for each immediate option, because these will be useful to feed into…

Step 8: Pro/Con immediate options

With all that in mind: back to basics. Basics Plus+, really. Pull together a hard pro-con list your what-nexts, being sure to include elements from all of the above.

I ended up at a point where I was loosely choosing between three very different jobs (again with the strategic blurring…).

My big thing #1, which is probably not broadly transferable: availability heuristic hits me hard, in some realms more than others. I’ve always thought of myself as someone who is exceptionally comfortable being uncomfortable, but it turns out I’m just comfortable being intellectually uncomfortable (brain stuff, new jobs, new places, new experiences) and far less so with regard to interpersonal instability. Parsing the choices I had on hand made that clear: once I began pinging between worry about missing out on knowns versus unknowns, the ridiculousness of that shot into perspective (tl;dr: FOMO is all around us).

But the most helpful conclusion? I had no bad options. Nothing would take me substantially off-course; nothing would be dull. The differences in outcome were qualitative and somewhat temporally interchangeable. (This was validating. Of course I was so confused.)  I suspect that’s part of the process, and that this whole thing is a path function rather than a state function: you end up satisfied precisely because you considered everything in depth, with the unknowns and sacrifices more tangible, and come to terms with choosing what you might be missing rather than floundering about.

That’s about it. I don’t know if anyone beyond my weird friends will find this helpful (and at the very least, those 16 hours of  tipsy snapchatting a few weeks ago might be a little less of a mystery).  I’ll be off mostly(?) camping(?) in sopping scrubland for the next six months – internet questionable – but I really like being helpful, so please drop me a line if you want to bounce ideas off of someone. And especially if this solved your whole life, or made you feel less alone. Always the goal.

Chaos Muppet Strategic Planning

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s