One of the most important things for your entire life is choosing what projects you work on.
If you choose your projects right, life will be very satisfying, full of achievements, every year will be a little easier and better than the last one.
If you choose your projects wrong, you'll get stagnation, be forced to re-start from scratch when things fail or get abandoned, and otherwise have a rather frustrating life.
And yet, it's rather hard for most people to choose what to work on. There's potentially... well, infinite things.
I'd like to recommend a guideline to you: only do 10-year projects or short projects, and almost nothing in between. Since switching to this view of the world, life's gotten immensely easier and better for me, I've been able to have a lot more successes, and deliver a lot more value to the world.
ADVANTAGES OF 10-YEAR PROJECTS
I'm not just talking about startups here, but these sorts of graphs are very illustrative. Via Business Insider --
These are two of the fastest-growing companies of all time.
And note that almost none of the gains in valuation came in the first two years of business.
This not unusual -- it's the norm. Here's Microsoft via Network World --
Note again that Microsoft made almost no gains its first five years... and its explosive growth happened from year 9 to year 14 of being in business.
Again, I'm not just talking startups here -- careers work similarly, as does making art, as does... everything?
In the United States, doctors are required to do undergraduate studies for about 4 years, 4 years of medical school, and then a residency which takes a few more years.
The whole time you're studying to be a doctor, you're investing a ton of time and resources (monetary and personal resources) into it... as a resident, you earn nothing and have a terrible stressed-out life (I'm friends with some doctors... I also used to be friends with some people in med school before they got into their residency programs, at which point no one heard from them ever again).
So it'd be pretty foolish to do a 4-year pre-med degree, 3 years of medical school, and drop out.
Seven years of your life burnt, lots of debt, nothing much to show from it.
Likewise, with any business that doesn't produce immediate gains, there's a ton of time needed to perfect the product, figure out your marketing channels, build out your team and learn management, fill any missing gaps in your skillset, etc, etc.
Therefore, I recommend you don't do things that pay-off in the long term only unless you know you're willing to commit to them for 10+ years.
There's also a lot of advantages to committing for 10+ years to one area:
*Being able to do things fundamentally correctly and soundly since you know you're going to be in the game a long time
*Most of the gains come from years 4-7 or later in many fields
*Certainty around what you're doing, life-clarity, and the ability to plan and put stakes in the ground for future years
*Not being an erratic flaky "ideas person" who always has new great ideas who no-one trusts to follow them through
*You gain surface area credibility and respectability naturally by being in the same field for a long period of time
SHORT PROJECTS IF YOU DON'T HAVE ANYTHING YOU WANT TO COMMIT TO
But, you say, you don't know what you want to do for the next 10 years?
There's an answer for that: do as short of projects as possible.
When I say "as short as possible," I mean that nearly literally.
Given two project choices that are even remotely comparable in how valuable they are, I'd recommend you always choose the one that completes faster.
There's a lot of practical implications to this.
"Start a podcast" is not something I think you should do casually. That's the type of project that easily dies; most podcasts get abandoned.
Instead, I would recommend you do a 4-part or 6-part audio series.
That's what Seth Godin did with his Startup School podcast from 1st October 2012 to 7 January 2013. He put out a 15-episode podcast, that was always designed to be 15 episodes, and then he was done.
I think 15 is even too long for most people; Godin, of course, is quite skilled and experienced, and has a lot of resources and knows himself very well.
So instead of starting a history podcast on Rome, do a 6-part series on the Roman Civil Wars or on Augustus's reign only.
What you'll find, when you think this way, is it forces you maximize getting your best ideas out there and collecting all the gains from them.
Likewise, it's very easy to turn a short project that goes well into a long-term endeavor.
If you do a 6-part podcast, and it goes great, you could either do another 6-part series afterwards. If that goes well, maybe you make it something you're doing for a while.
I'd never, ever recommend anyone who isn't already an established writer sits down to write a book -- the vast majority of books never get finished. Think novella instead of novel, short story instead of novella, essay or series of essays instead of a nonfiction book.
Life gets a lot easier when you can focus on a single major endeavor at a time.
If you're kind-of sort-of writing a book, or kind-of sort-of making a new podcast, life kind-of sort-of sucks. It's easy to become unfocused and ground down.
Whereas if you're making a 6-part series, you complete 4 of them, but then life gets in the way -- you can always take a week off work, go get a cabin, and get the damn thing finished and out there. It's very possible to sprint to completion with short projects.
The "Completion Muscle" is critical to build.
I think there's very few things in life as devastating as quitting something that's nearly complete. It entrains you to expect things to fail, it makes quitting easier in the future, and it's a waste of all the time and resources that came before.
With that said, it's often very practical to abandon a project if something better comes along. If you start a podcast, it's kind-of sort-of working out, but then you get offered your dream job -- well, sure, it makes sense to quit.
But again, if you were working on a series instead of a full podcast or a full book or whatever, you could blitz it out and finish it before starting the new job. That means you get more experience at completing things, which is a critical skill and habit to build.
With short projects, you're able to focus on the finish line, do a steady strong burst of work to get there, and you'll very likely remember to collect all the gains early since you know it's a short thing.
And you can always do another one.
MAKING SHORT PROJECTS ADD UP
The main danger or seeming downside to short projects is that they don't "add up" the way that starting a company or writing a book "adds up."
That can be mitigated and planned-for.
Consider doing most your projects in the same broad field, market, or using the same skillset.
If you know what field you want to be in broadly, that's a great time to do all your projects in that field. If, say, marketing automation was your jam, you could do short projects in open-source, consulting, throw a small event or mini-conference, do a 5-part podcast or essay series on the fundamentals of marketing automation, write a simple white paper, things like that.
This lets you see what form factors of producing you most enjoy and are most well-suited to in your chosen field, lets you confirm that you like the field and want to operate there for a long time, and lets you start building a good reputation in that field.
Ensure you consolidate gains along the way.
The simplest version of this is some way to stay in touch with people you meet and interact with + a very lightweight portfolio.
Setting Up a Lightweight Portfolio --
The extremely talented Eden Full, who I've had a few collaborations with, is a great example of this.
Check out her website, I think she gets it perfect --
In particular, check out the "Press" and "Projects" sections -- something lightweight like that is really the 80/20 version of consolidating gains from different projects and activities until you find the one or two things you're willing to commit 10+ years to.
If you want to make things a little more virtual, Greg Nance -- also an exceptional person and terrific CEO -- does a good job of that on his Strikingly page:
Strikingly is a great tool for building a simple site, or you could use Weebly, or Exposure.co. These are all very lightweight sites with a free plan; just make sure you list the projects on there and do a little recap after each one. It should take no more than a single Saturday afternoon, if you go really slow, to write up your projects. (You could even just use LinkedIn, but I think there's an advantage to building your own simple site.)
For staying in touch with people --
*Get on FullContact and religiously add important people you meet to it with some tags about them. It's free, it's got a great Gmail integration, and a great native desktop version. I tested all the contact management software; most of it is terrible, but FullContact is good enough. That was recommended to me at an event held by Taylor Pearson -- I forget who recommended it, perhaps Zack Kanter or Austin Brawner or Casey Ames? (If it was you, let me know and full credit to you; it's the best there is right now.) It's also free for most common usage.
*If you've got customers, users, buyers, or stakeholders at all, create a free mailing list on Mailchimp.com and make sure you mail them at least once every three months with an update of what's going on with you. Do this ASAP if you're doing multiple projects in the same field. No one regrets doing this, and lots of people regret not doing it sooner. It's not critical if you're doing projects in different fields, but the day you do your third project in the same field is the day you better be doing this. Just trust me and do it, it'll be obvious why later. Mailchimp is free for your first 2000 subscribers anyways, so it's not a big commitment, just a few hours to set it up and an hour to update people once every three months at a minimum.
Developing Universally Valuable Things
Kai and I wrote a whole book about this, Gateless, so I won't bang on this drum too hard -- but there's a number of things in life that are universally valuable.
One of the biggest things you need are really virtuous, uplifting, exceptional friends and project partners; people you can do future collaborations with.
Doing short projects is a great way to see if you "click" and can work together.
In the short projects I've done, I've had some collaboration with... I don't know, at least 100 people over the last 5 years? Every year at GiveGetWin Summer Camp, there's around 10 mentors, people who help out on the ground, and all the participants -- these are people I get to know really well who go on to become long-term friends.
This year, among others, Danielle Strachman and Michael Gibson from the 1517 Fund gave a terrific lecture and it was the start of a nascent friendship; they're wonderful people, people I'm excited to know for the next decade of my life. Jesse Sussman and Lisa Larbi were among some of the terrific attendees and are now making a big mark at GiveGetWin Musician and GiveGetWin on Campus. There's a value in the work itself of course; there's a joy in helping young people realize their potential in entrepreneurship and leadership, and funding worthy philanthropic projects, but there's also a great joy in meeting people who are wonderful to know for coming years. Jesse and Lisa presumably won't be at GiveGetWin forever, and yet I'm so honored and thrilled to get to know a couple exceptional people and I hope to know them for decades to come.
The same of course is true of the GiveGetWin Tour -- Taylor Pearson and I became much closer when traveling and collaborating together on those three weeks and in the planning phases beforehand, Angela Cheung and I went from being strangers to being friends (and she's a wizard; she's incredible at what she does), and I got to know some wonderful people on Tour.
Really exceptional friends and colleagues are one of the most valuable things in life, and you can pick projects that are good at cultivating them.
You likewise can pick projects at the edge of your skillset, or which require a single new valuable skill (marketing, public speaking, writing, various tech/programming, etc) and develop those through short projects.
In this way, with every project you complete, you have more universally valuable things for your next projects and for your life going forwards.
And yes, I think shorter projects are -- all else being equal -- much better for developing universally valuable things.
THRESHOLDS TO COMMIT FOR 10+ YEARS
I would recommend against committing to a 10+ year project until (1) you know you really love the field and all the critical stakeholders in the field, (2) you know you're well-suited to the day-to-day work in that field, (3) you're sure the enthusiasm and love of the field won't wear off in a year or two, and (4) you've got the right team to work with who also can commit long-term.
If I could go back in time, I would've started GiveGetWin differently -- I'm on my 5th year there, but in the beginning, I started with too ambitious of a goal and not understanding enough of the day-to-day work needed to make the organization successful. In fact, the way I would have started it would look a lot like what we're doing now -- there's a series of projects that happen every year (GiveGetWin Summer Camp III is already scheduled for June 2017 at UChicago, GiveGetWin Tour V and Tour VI are already in planning phases for Autumn 2017 and Autumn 2018), and I would have only focused on the macro-aggregation stuff once we hit some critical thresholds, funded the first charity projects completely, and hit a bunch of milestones. We eventually hit all of them and hit our stride at GiveGetWin, but it could have happened 1-2 years faster if I'd worked on a more short projects basis when starting out, instead of (very silly over-ambition in retrospect) trying to change world GDP right away.
I likewise had a number of semi-promising business-y things for years, but they didn't add up. It hurts when you get to your first $100,000+ in revenue but realize you don't like the market, or the team isn't made up right.
The last point is so critical that I'll underline it here -- if a domain where the gains come in 10+ years requires a team, you should absolutely stay on a projects-only basis until you have some people you really love and work nearly perfectly with on projects before committing.
Nick Winter of CodeCombat made a much smaller and less ambitious project, the Skritter app, with friends of his before going on to start the now YC-funded and doing great CodeCombat with the same people.
I spent a few years of my commercial life only doing consulting and short projects until I had both a market that I really loved and a very close colleague I work exceptionally with in Kai Zau; then and only then did we start Ultraworking. We worked on around a half-dozen to a dozen large-ish projects before going into business together for the long-term.
Likewise, at Ultraworking, we tested four different offerings last year -- each of them as a project. The most successful and promising, the Ultraworking Pentathlon, customers loved it even though the tech was very very creak-y behind the scenes (it worked, but it was duct-taped together on the back-end).
When people loved the Pentathlon and we got rave reviews, we settled on that as a core product to develop. Our first ideas were okay, but were either not as good, not as useful, or not as scalable.
Knowing we're in business for 10+ years means we can do things fundamentally correctly.
We spend a lot of time on internal culture, on automation, on building great infrastructure and investing in customer experience. Again, this is only really possible because Kai and I know we're going to be in this game for the forseeable future, we're both committed, we both know each other's strengths and weaknesses very well, and we both like working together, like the type of work we do, and love the customers we work in the space.
If you don't have an exceptional collaboration with someone already, don't start a company with them.
I know that sounds obvious, but one of the chief reasons companies fail is due to founder conflicts and disagreements. This can all be mitigated by doing short projects with multiple people. The ones that go the best, work with them again -- and then again, until you know you love working together.
Yes, the process takes a couple years, but it's much better than working on something promising with someone you don't know for 2 years, having some initial traction, and then having your cofounder bail out or getting into so much friction and conflict that you can't keep going.
Meanwhile, if you did a lot of projects, you obviously won't become cofounders or partners with most people you work with -- but you do build a great network of people you know much closer than mere acquaintances. There's something special about doing short projects with people to get to know each other very quickly.
Well, as short as possible. Months, at the most. Weeks are better than months, though.
And a weekend is better than a full week!
If that sounds unexciting, well, I'd say just try it out. You can get a lot done in a single focused weekend towards a single outcome. If you can complete a cool project in a single weekend, then you can do somewhere between a dozen and 50 cool projects a year until you find where you really hit your stride.
The big world-changing magic comes from the 10+ year stuff, that's true, but you don't have many 10+ year bets in you -- you should scout the landscape carefully through short projects, find people you love to work with, find a market and type of work you thrive at, and develop universally valuable things along the way.
Then, when you're ready to commit to your 10+ year thing, you can truly commit, because you know it's going to work.
Oh yeah, and if you want a huge productivity boost and kicking 2017 off with a bang, we'd love to have you on the next Ultraworking Pentathlon.
I absolutely agree about having some kind of lightweight portfolio. It makes it easy to show off your work. It answers the question "what does s/he *do*?" for potential collaborators. Better than either of those, it makes you work on things you can communicate to others. For short projects, either learn a skill (or micro-skill) you really need or work on a project that communicates a specific strength to others. Either one is a permanent asset.
Paulo asked commented on Internal Scorecard #1,
I think there's three questions here:
1. How do you coordinate multiple projects that don't overlap?
2. How do you know how much is too much to be effective?
I'm thrilled that Tynan is coming to you with two things -- first, he's offering a breakthrough session through GiveGetWin. It's geared around doing more of the kind of excellent work you want to do, becoming more internally focused with your emotions, having a more enjoyable life, building great habits, and producing a lot of value in the process. There's five spots, so check it out now.
Second, we have this wonderful tour-de-force interview: it starts by covering how Tynan made the shift from unfocused to focused, how to derive internal enjoyment from things, useful actionable exercises you can do right now, Tynan's method and mindset for producing creative work consistently, how to set up great habits and an excellent mental and physical work environment, and how to make blogging work and similar endeavors work for you.
Total Focus; Total Enjoyment by Tynan, as told to Sebastian Marshall
When I turned 30 and I had a minor freak out… I thought, "I'll be 40 in not long, and then 50… there's things I want to do in my life, and they're not happening at this pace."
Before that, I had a general idea of things I wanted to do and have in my life, but I went about in an unstructured way. It was good in a lot of ways. It made be a broad process, but not much depth.