The last couple of months have been full of decision points for me, both personally and professionally. Everything has been on the table, and everything has been in potential flux.

Having worked in early stage startups pretty much continuously since 2003, it's possibly been less stressful for me than this level of uncertainty might be for others. Still, going forward, I would like to be more intentional about how I'm building my personal life. And while this might come across as a little pathological - have I jumped the Silicon Valley shark? - it seems like some of the tools we use to quickly understand businesses might work here, too. I typically don't like imposing frameworks on my personal life because you lose serendipity, and the experiences worth having are usually precluded by adding too much structure. I think humans are meant to freestyle; living by too many sets of rules closes you off to new possibilities.

Conversely, having guiding principles, and treating them as a kind of living document, could be helpful. It's the same thing I've advised so many startups to do: building a rigid business plan destroys your ability to be agile, but writing out the elements of your business forces you to describe and understand them. The Stanford d.School style Instant Business Plan, where the elements are literally Post-Its than can be swapped and changed, is a far better north star than a one-shot document. I think the same approach could work well for a life plan: a paper document where changability is an intrinsic part of the format, but you are nonetheless forced to express your ideas concretely.

Why Post-Its rather than a document or a personal wiki? Post-Its force you to summarize your thoughts succinctly, and can easily and tangibly be replaced and moved around. Other options carry the risk of being too verbose (which is counter to the goal of creating an easy-to-follow north star) or unchangable (which is counter to the goal of creating a living document that changes as you learn more and test your ideas).

Here's what it could look like, as a rough version 0.1. It's inspired both by the Stanford d.School Instant Business Plan, and a similar document used for startups at Matter. Don't give yourself more than 90 minutes to put this together:

Hi! I'm [halfsheet Post-It]
An elevator pitch of you, that doesn't focus on what you do for a living (that will come next). It's what we call a POV statement, which contains a description, a need and a unique insight. Example: Hi! I'm Ben. I'm a creative third culture kid who loves technology and social justice, but whose first love is writing. I need a way to stay creative, maintain work/life balance, and do meaningful work that also allows me to live a comfortable life.

I believe the world is [no more than three regular Post-Its]
Three things you think are happening in the world. This is a way to express your beliefs. Example: Experiencing unprecedented inequality that is harming every aspect of society; In the early stages of an internet-driven social revolution; Moving beyond arbitrary national borders. How would you test if these trends are real?

I make money by [halfsheet Post-It]
Here's where you get to describe what you do for a living. Example: Providing consulting and support to mission-driven early-stage technology companies and mission-driven incumbent industries, both from a strategic and technological perspective. Sometimes I write code but it isn't my primary value.

My employers are [no more than three halfsheet Post-Its]
Who typically gives you money? As a category, not a specific company. Example: Early-stage, mission-driven investment firms who need an ex-founder with both technological and analytical skills to help source and select their investments; early stage startups who need a manager with an open web or business strategy background; "legacy" or "incumbent" large organizations like universities and media companies who need an advisor with technical or startup experience.

My key work skills are [no more than three regular Post-Its]
Which skills are core drivers of your employment? Example: Full-stack web development and technical architecture; Trained in design thinking facilitation and processes for both ventures and products; Experienced startup founder who has lived every mistake.

My key personal attributes are [no more than three regular Post-Its]
What aspects of your personality or the way you act are you proud of? What do you think other people respect you for? Example: Bias towards kindness rather than personal enrichment; Writing and storytelling; Collaborative rather than competitive.

My key lifestyle risks are [three regular Post-Its]
What are the things that keep you up at night about your lifestyle? Specifically, in the following three areas:
Happiness: Risks to your ability to be a happy human (this is different for everybody)
Viability: Your financial risks
Feasibility: Risks to your ability to achieve the lifestyle you want with the time, geographies, and resources at your disposalExample: Happiness: I don't time to spend being social or taking care of my health; Viability: I need a minimum base salary of around $120,000 to cover my costs in the San Francisco Bay Area; Feasibility: It might not be possible to maintain the quality of life I enjoyed in Europe without a significantly higher salary.

My key work risks are [three regular Post-Its]
What are the things that keep you up at night about work or your ability to find it? Specifically, in the following three areas:
Workability: Risks to your ability to have a satisfying work life (this is different for everybody)
Viability: Risks to your value in the employment marketplace
Feasibility: Process or ecosystem risks to your finding the employment you want with the time and resources at realistically at your disposal
Example: Workability: I am seen as largely a developer; Viability: I don't have experience working in a large tech giant in a management role, or equivalent; Feasibility: Most jobs are filled within a network and I'm not sure I have the connections I need to get to the jobs I might want.

Risks parking lot
As you figure out what your key risks are in each area, you should keep track of the ones that don't quite make the cut. It's useful to understand what they are, but as your life plan evolves over time, you might want to swap them out and bring them back into the key risks area.

Above all, to be successful, I need to [three regular Post-Its]
The definition of success varies for everyone. Some people are money-driven; some people prioritize other goals. What are the things you need to achieve to be successful? Specifically, in the following three categories:
Happiness: Your ability to be a happy human with the work and personal lives you want
Viability: Your ability to earn money and cover your costs
Feasibility: Your ability to practically achieve the things listed in happiness and viability with the time and resources realistically at your disposal
Example: Happiness: Regularly spend time with inspiring, mission-driven, kind people at work and in my life wihle taking care of my health; Viability: Get a job that comfortably covers my San Francisco Bay Area costs on a recurring basis; Feasibility: Gain marketable skills (MBA? CPA?) to add to my existing technology and business experience.

My key next steps are [three regular Post-Its]
This is what everything has culminated in. Based on the risks and the primary needs expressed above, what are the concrete next steps in the three key areas? Spending more time doing research or thinking doesn't count. It's got to be an action you can take immediately. Again, these are in the following categories:
Happiness: Your ability to be a happy human with the work and personal lives you want
Viability: Your ability to earn money and cover your costs
Feasibility: Your ability to practically achieve the things listed in happiness and viability with the time and resources realistically at your disposal
Example: Happiness: Set clearer boundaries and set aside time to spend with friends and exercising. Viability: Identify and remove any unnecessary recurring expenses. Feasibility: Sign up to do some pre-CPA accounting courses, to allow you to better analyze startup businesses.

Finally, there's one more thing: get feedback. Once you've put this together, find someone you trust - or better yet, multiple people - and talk them through it. The best possible scenario is if a few friends all do this for themselves, give each other feedback, and then iterate.

Good luck! And please give me feedback. It would be fun to turn this into a framework for solidifying life decisions and more concretely describing the choices and challenges you have, in order to make them easier to deal with a task at a time.