“I’m gonna put 1,000 songs in your pocket.”
In the movie Jobs, it ends with him telling his daughter he was going to invent the iPod. Years before any of us knew it, Steve Jobs was going to not only put Apple back on the map but make it one of the most successful companies in the world. There are way too many Steve Jobs stories in self-improvement books, but I included one because it illustrates a concept you must understand to have long-term success.
The concept is called definite optimism. When it comes to playing the long game with your life, the equation is pretty simple. Aim yourself at a certain type of life and work at it for a really, really long time. Sexy, right?
Back to Jobs. Imagine having an idea for an entire product line, one that nobody even knew they wanted, and spending a decade methodically planning the launch of each product. The iPod, iPhone, and iPad would be released sequentially over the span of years.
The iPod made sense to start with as there were already MP3 players on the market (that weren’t very good). He released the iPad before the iPhone because he wanted to perfect the technology for the glass surface before releasing his piece de resistance.
It’s hard to have that level of foresight and belief in your own ideas, but if you can think in the long-term while working hard in the short term, you can achieve whatever level of success you want…within reason.
Maybe (probably) you won’t be the next Jobs, but what else could be in store for you if you put together multi-year plans and followed through with them?
This isn’t the first book about long-term planning, nor will it be the last. I’ll try to make this different by hammering down on the philosophical importance of long-term planning and dive as deep into the nuts and bolts as needed in order to make this idea stick. If you haven’t noticed, that’s basically what this entire book is.
Definite Optimism: The Subtle Art of Long-Term Planning
The idea of definite optimism comes from the book Zero to One by Peter Thiel. The book includes core subjects like the different definitions of optimism and pessimism:
- Indefinite pessimists — They see a bleak future, but don’t know what to expect
- Definite pessimists — Doomsday predictors
- Indefinite optimists — Thinks life is just going to improve on its own
- Definite optimists — Long-term planners and thinkers with answers to future problems
Theil cites the lack of definite optimism as the cause for many of our societal problems. See, your parents and their parents grew up in a time where technological innovation and progress was happening all around them. Imagine being a middle-aged or old person and the shifts in technology they’ve experienced.
During these times, tracked careers worked out. The innovation and progress, mainly industrial and corporatists, provided a pretty clear path to success. Boomer parents with tracked careers went on to have kids who they tracked careers for.
In 2019 and beyond, though, tracked careers won’t work. You can’t just get your degree and coast for decades anymore. The future isn’t going to unfold on its own. You have to be conscious of your talents, strengths, and tastes then cultivate a tailor-made career around them.
That is, unless you want to see how the “powers that be” plan everything for you. After you find a field you want to stay in, make long-term commitments and plan the next steps well in advance.
Using advice as autobiography, I’m going to tell you how I plan for my future. In the beginning, I was just trying to get traction.
In the earlier chapters, I discussed the process of finding your strengths and deciding what to do with your life.
I advise a 90-day test period to get your feet wet, then another six to 12 months to practice before you’re serious. Once you’re serious, you can plan your life using these timelines.
25+ Year Plans
I learned this idea from the author of The End of Jobs, Taylor Pearson. Having a long, long, long-range plan for what you want your life to be like can inspire you when times get tough.
The point of this exercise isn’t to reach an exact destination but to paint the picture of what you want your life to be like. Here, you write down the wildest most insane dreams you have that you feel stupid even writing down.
You can write these goals for:
- Your career
- Your health
- Your relationships
- Your spirituality and contribution to your community
18 Months — The Benchmark From a Legendary Business Expert
There’s a nice little book called Managing Oneself by Peter Drucker that packs more wisdom in fewer pages than almost all other business books.
One section talks about how to plan your career. He suggests using 18 months as a timeline to measure your career progress.
18 months is enough time to put enough focus and effort into a career track to see if it works for you. It’s also not so long that the goals you set will be inaccurate and unuseful.
You set your overall goals for the next 18 months and then break them down into 90-day intervals (I’ll explain below). Then, after 18 months you compare what you said you were going to do with what you actually did. You use this qualitative information to make decisions for the next 18 months.
The goal here is to avoid aimlessly wandering through your career and life with no benchmarks to tell you if your effort is actually worthwhile. The goal is not to become a robotic planner who measures all minutiae. You just need to aim somewhere, because if you don’t aim, how the hell are you going to hit a target?
Quarters are a standard benchmark. Many businesses track their fiscal success in quarters. We’re used to the idea of quarters being defined periods of time that make for useful measurements, e.g., sports.
Taking a year or 18 months and breaking them down into 90-day sprint intervals keeps you focused in the intermediate. This isn’t so much about meticulous planning as it is about reinforcing your goals from the top down. Psychologically, it will feel good to knock off a major milestone four times each year. It’ll also keep you from major bouts of procrastination.
For each 90-day period, you can choose one major goal or piece of a project you want to finish. My most recent 90-day period was spent writing the first draft of my book. The next 90-day period will be for editing and finishing the marketing plan for the book.
After you decide your overarching goal, pick actions you can do each day and week to make sure you’re staying on track. My action’s simple for this period — work on the book daily. Each week, I’d take time to get a bird’s eye view of the process to make sure I was creating enough content to hit my deadline. I’d also use this weekly check-in period to catch up if I felt like I hadn’t written enough.
These are all loose guidelines. The philosophy itself matters more. Having long-term definite benchmarks you can use to measure your progress matter more than the benchmarks themselves. The goal here is to have a framework you can use, not get bogged down in the details.
Planning > The Plan Itself
They say “God laughs at your plans.” Becoming a definite optimist doesn’t mean that things are definitely going to work out the way you want them to. Not even close. The point of planning isn’t to hit every single goal on the exact date. Simply having a plan is better than no plan.
Far too many of us wander aimlessly. Not because we’re not capable or skilled, but because we never take time to conceptualize what we want. Daydreaming doesn’t count. The act of articulating what you want in a tangible way does. That’s it.
Think about this deeply. Have you ever really taken the time to deeply think about and attempt to map out your future? Have you spent even an hour in silence with a notebook jotting out a rough plan? If you answered yes, you’d be in the minority of people.
It’s quite odd to have something so valuable as life yet utilize it so poorly. Why do we do this? Maybe it’s our DNA. Maybe it’s society’s fault. Perhaps there is no specific answer. It probably doesn’t matter, either. What matters? Your life matters. What you decide to do with it matters. And you only have two choices — try to plan out your future, or don’t.
How has the latter panned out for most of us? It became easier for me to write about self-improvement after I stepped off my pedestal and took off my rose-coloured glasses. Once you look at life more objectively, more analytically, spending the time to create the life you want just seems like a better idea. Take inspiration out of it. It’s pragmatic to care for your own life to the greatest extent possible. Do it.
I’ve been at this for about five years. Did I knock off every item from some 5-year plan I wrote back then? No. The funny thing is…I often write notes and plans only to never look at them again. Notebooks upon notebooks of information I don’t even use.
The process of filling up those notebooks with plans, ideas, and goals has moved me in the right direction, though. I may not read over the notes word for word, but I remember the gist of what I wrote down and I deeply understand the intention behind the notes.
Over time, my ‘evil plan’ has become a constant in my mind. I know the mission I’m on and I work at it every single day. Planning is a means to an end, the end being a life where you don’t have to constantly think about your next move and have an intuitive sense of where you want to go.
You use your plans to get enough traction where quitting is no longer an option for you. Of course, all the planning in the world won’t help without a system to foster productivity.
The Life-Changing Magic of Aiming
“One of the great insights of psychoanalysis is that you never really want an object, you only want the wanting, which means the solution is to set your sights on an impossible ideal and work hard to reach it. You won’t. That’s not just okay, that’s the point. It’s ok if you fantasize about knowing kung fu if you then try to actually learn kung fu, eventually you will understand you can never really know kung fu, and then you will die. And it will have been worth it.” — The Last Psychiatrist
Why create plans for your future and follow them, only come to find you just want more? Why not just be content with what you have and live in the present moment? Those are valid questions. My answer? You’re not wired to be content and live in stillness.
You’re wired to aim.
Humanity is one big aiming mechanism, which is why we enjoy the technology and civilizations we have now. To ignore this mechanism is to ignore what makes you…you. You want to build, aim high, focus on something, live a life of meaning, all of it. You’re here because you’ve tried the alternative and you didn’t like it all that much, did you? Aiming will help more than you know.
I still remember a pivotal moment in my life. I was folding laundry at my then girlfriend’s apartment listening to a lecture from the motivational speaker Jim Rohn. He said, “5 years from now you’ll arrive, the question is, where?” He went on to talk about self-improvement and making a living you love, stating that the goal itself wasn’t the material gain, but “the person you become in the process.”
There’s something magical about aiming for something out of your reach and working toward it that people can only understand once they do it.
I look back at where I started — almost penniless, full of despair, no hope or options. I think about the tiny moments here and there that added up over time — reading a book, writing a blog post, joining a club, giving my first speech, writing a book — to the life I live now. I most definitely think about the struggles, the walls I hit, the feeling that I was just about to crack the ceiling but wasn’t quite there.
All of this combined equals joy. And I’m not even close to done.
I still have that document with my 25-year goals. I’ve crossed some of them off. Now the ones that seemed super audacious and near-impossible to pull off seem…doable. The more you work on your dreams, the higher the level of confidence you gain — not because you’re something special, but because you’ve experienced the outcome of aiming and working hard that takes you from ordinary to extraordinary.
You can’t fathom the idea of work being more important than talent until you experience the benefits of it yourself. Then, instead of resting on your laurels and patting yourself on the back, you keep going.
Why? Because what the hell else are you going to do? This is the entire point.