What’s Your Life Strategy?

There’s a lot of discussion about specific tactics you should use in life to become successful: what productivity app you should use, which exercises to be fit, where to invest your money. Missing from this is the question of how do you think about the big questions in your life? Not just where you spend the hours and minutes, but the months and the years.

I don’t presume to have the perfect formula figured out, but I wanted to start the discussion by sharing how I think about these things in my own life. Maybe my approach might be helpful to you if you’ve been struggling with these questions.

1. Projects lasting 1-2 years should have the spotlight.

When I started out with goal setting, a lot of advice I read suggested making 5, 10 or even 20 year goals for your life. Other authors focused on much shorter intervals—thirty or twenty-one day trials.

In my opinion, projects of a year or two are the most useful scale to focus on for achievement.

Projects of this length are meaty and can actually enact meaningful change. If your focus is exclusively on month-long or shorter goals, you may miss out on the benefits a concerted effort to really make a difference in something might make.

Longer goals, however, I’ve found aren’t terribly useful, either. This isn’t because all successes happen in a timeframe of under 24 months, but because the act of growth causes so much change that plans made for five years or a decade will often be conceived of incorrectly by that time. The assumptions and theories that went into them will change after a year or two’s worth of experience, so it’s better to focus on a project that won’t drift completely in the meantime.

2. Only have one main project at a time. Everything else is a side-activity.

Once you pick your main projects, only have one at a time. This is your priority and it takes precedence over any other goals.

This doesn’t imply that you don’t work on anything else other than your single project. Just that when conflicts arise and you’re forced to choose between working on one or the other, you always side with your main project.

Picking the one project and sticking with it requires a lot of discipline. It’s easy to get halfway through a project and want to skip to something else. Committing in advance has been enormously helpful to me, even if it sacrifices some flexibility, because many projects I start to feel are “duds” end up becoming the ones that make a difference. Patience matters.

3. It’s okay to fail at your side-activities.

A corollary of having a single main project is that your side goals will fail sometimes, due to lack of input or effort. That’s okay. That shouldn’t be viewed as an error or mistake, but a normal part of the process.

If I’m working on a big project for my career, and I slip up and stop going to the gym as often as I’d like, that’s not simply laziness on my part—that’s a side-effect of a system which demands focus. I can pick myself up and try to start a new gym habit, but I can’t expect perfection on every project, or beat myself up about letting side-activities slide.

4. Oscillate between big projects and smaller ones.

My rhythm in life for the last decade or so has been one year, a big project, with 12-18 months of “down time.” The down time here isn’t a time without projects, but one where I fit shorter projects that need doing in the gaps. Since my big projects are usually career or learning related, this is often where I fit in projects for other goals (fitness or travel).

This oscillation is good because the single-project focus, while it does optimize for achievement, often leaves numerous smaller things that get somewhat neglected. Switching between having a big project and a series of smaller projects prevents your life from getting too misaligned from an obsession.

5. When in doubt, build assets.

Often it’s not clear what needs to happen in order to succeed in some area of life. For years working on my business, it wasn’t clear what I needed to do to make it work. I knew I wasn’t making the kind of income I needed, but it also wasn’t obvious what I could do differently to make that happen.

This ambiguity about what will create success is incredibly common. You may not know what you need to do to improve your career, your dating success, your health or finances.

Sometimes more education is the answer—read more books, do research. But other times the ambiguity is fundamental. You can’t read the answer in a book because it doesn’t exist there (or the answers are so numerous as to create a new challenge of figuring out which answer is right for you).

In these cases, my default mode has always been to try to build generally useful assets. This is to switch out the question of “what should I do?” with “what would be useful, generally speaking?” The former question may not have a clear answer, but the latter usually has many things which could probably help. Sometimes success is simply answering this question enough times that the accumulation eventually breaks through.

For instance, if you’re luckless in love, you might decide to start working on your communication skills, start building a deeper social network, improve your fashion/appearance or learn improv to become funnier. It’s not clear any of these projects will bring success, but if you build enough assets in this direction, you’ll probably improve your chances.

6. Know how to separate your “cash cows” from your “home runs.”

A cash cow is a euphemism for a part of a business which reliably generates a lot of revenue or profit. It may not have enormous growth potential, but it is something which can pay the bills and solve immediate financial problems.

A home run is something which, if you strike out, may not bring anything, but if you connect, it might push you to a completely different playing field.

Many areas of personal development have a similar dichotomy. Some things are well within your understanding of how to achieve success, and simply require some effort. Other things are new, scary and uncertain, but have the potential to be really big.

You need to split your time between these two types of efforts, and which should be your main focus depends on where you sit. If you’re dealing with immediate crises, a “cash cow” project should be your focus. If you’re not in imminent danger, “home runs,” have the greater long-term potential.

7. If you can endure the worst case, the best cases take care of themselves.

All of my plans are pessimistic. I focus on what might go wrong, not speculating about what might go right.

This may seem like a mindset doomed to fail, but I’ve found quite the opposite. When you manage and control the worst case, fear and anxiety are less likely to overwhelm your thinking. Since you know you can endure the worst outcome, then anything becomes tolerable.

Part of this is asking whether I could sustain a failed outcome. What if a new project completely goes bust? What if I make no progress? Could I keep going, or would failure to reach a certain outcome be a disaster with my plan as it is now?

But an even bigger part of this is expecting a certain amount of behavioral failure. What if I get sick? What if this takes me longer than I had anticipated? What if this turns out to be harder than expected?

When you take this mindset, you start to feel a lot luckier. Why? Because when you’ve planned and prepared for the majority of negative possibilities, then the “random” events you tend to encounter are biased towards the positive. You get a lucky break, or something succeeds more than you had expected.

Fine Tuning Your “Life Strategy”

These are a few concepts that I think guide me in planning and thinking about my life at the scale of months and years. What interests me isn’t that this represents a kind of “correct” answer, but that it forms a particular style, well-suited to my life and tradeoffs.

Articulating your life strategy, even if you don’t think you have one, is quite useful because sometimes you’ll notice contradictions. You’ll claim focus is important to you, but then chastise yourself when you don’t do everything perfectly. You say you want to split your energies between work and personal life, but work always fills the spotlight.

It’s also useful to notice and try to articulate other people’s life strategies. This can open you up to alternatives you may not have considered. One friend of mine operates off the mantra, “Every year something different.” And moves apartments, changes jobs or otherwise does something quite different every year or two. Another friend of mine optimizes for flow, not aiming at any destination in particular, but adjusting slowly adjusting his lifestyle.

What’s your life strategy? How do you feel it could be better to make you happier and more accomplished? Share your thoughts in the comments!

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