Reverse engineer the best time of your life

Everybody has a "best time" of their life. Maybe it was the summer you spent hiking the Appalachian trail, or a semester abroad during college, or the second half of the first year at a new job (after you'd mastered the work and before it became routine). But why should the "best time" of your life be some time in the past? With some clear thinking and some effort, you can recapture what was great then for today.

Reverse engineering means figuring out a design from a working example. (As opposed to regular engineering, where you start with theories and principles of what ought to work and then create a design from scratch.) If you're trying to build some something new or better, then regular engineering is probably the way to go. But if you've got a working example that's exactly what you want more of, then reverse engineering is often cheaper and often produces a better result. And what is more precisely "what you want more of" than the best time of your life?

The best of times

What makes one time better than another? It's different for everyone, of course--otherwise your high-school guidance counselor would have given you a pamphlet with all the answers. Certain threads show up repeatedly, though, so we've got a pretty good idea of the sorts of things that matter. The key is to figure out the right mix--and any elements that are unique to you.

Note that it's okay to have more than one "best time." In fact, the mark of complete success will be when a question about the best time in your life prompts you to say, "How can I pick a best time, when all the times were so very good?"

The place to start is with some deep thinking about those "best times." What was so great about them?

Were you doing important work?

At a superficial level, many people remember a lazy summer or an island vacation as the best time of their life: They had minimal responsibilities. This is great for a few weeks, but it doesn't wear well. Much better is to do work that matters. And yet, there is also much to be said for responsibilities that don't weight too heavily on you. In this as in many things, it's important to strike a balance--and my advice is to look at your own experience for clues to the right balance for you.

Were you part of a team?

Often the best times of your life will be times when you were doing something as part of a common endeavor. Sometimes you will be part of a team working together on a common project. Other times you might be part of a community of people working individually on related projects. One of the best times of my life was the six weeks I spent at the Clarion science fiction and fantasy writers workshop. We were all working on our own stories, but also working together to learn how to write great fiction.

Were you optimally challenged?

Whether at work or at play, people thrive when confronted with tasks that are difficult enough to be challenging, but not so difficult as to be frustrating--or, at least, not constantly frustrating. Here again, what's optimal is different for everyone, both in terms of the level of difficulty (which should match your ability) and in the degree of frustration. Some people thrive in an environment where their successes are preceded by months of failure, while others prefer to achieve some level of success every day.

Were you self-directed?

Another reason that vacations tend to be remembered fondly (besides the minimal responsibility) is the maximum freedom: They could set their own agenda--or have no agenda at all. Closely related to this is being in control, at least of the things that matter most to you. Of course, having someone who's both wise and clever be in charge has upsides of its own. There's a whole spectrum on the continuum from being micro-managed to being footloose and fancy free. The best times of your life were probably spent when you were in about the right place on that continuum.

Were you respected by your peers?

There aren't many things more important than having your peers think well of you. Parents and teachers sometimes say "It doesn't matter what other people think," but that's a lie (even though self-respect is even more fundamental). Of course, you have to be careful when happenstance throws you in with a bunch of creeps, slackers, or losers. Choose your own peers; don't let circumstances choose them for you.

There are lots of other factors to think about. You were probably doing new things that interested you. You were probably learning new things and developing new skills. Perhaps you were interacting with people who were different from you. Perhaps you were advancing a cause that you believed in. Perhaps the challenges you faced were divided between physical and mental in a way that kept you both fit and alert. No doubt there are many factors I haven't thought of--including a few that are unique to you.

Think about what it was that made the best times of your life so great. If you're a list-making sort, make a list.

Times versus moments

Some of the best times of our lives are not so much periods as they are moments. Those can rarely be recaptured. You only get one first kiss; the birth of your first child happens once at most.

Sometimes a great moment can color the times around it. If you sank a three-pointer at the buzzer to win the championship game, that will likely make that whole season seem especially good in memory.

Even in the moments, though, there are the clues as to what makes one time better than other--and that's what we're looking for. What it is about some particular moment that makes it great? Often it will be the sort of thing mentioned above: You overcame a challenge, your contributions to a group effort were recognized, you took a stand and turned out to be right.

Make these times like the best times

When you're just making a naked comparison between, let's say, the months you spent backpacking in Europe and your current life working in a cubicle (or the year you spent sailing around the world the world and your current life as a stay-at-home mom) it seems pretty tough to make these times more like those times. That's why we looked at the characteristics that went into making those times great. What you want to do now is introduce those characteristics into your life today.

At the most basic level, this is easy: Do more of those things that you used to do then. (Make time by doing less of what you're doing now.) If your "best times" were, as many people's are, when you were a student or just out of school, you probably had less money then than you do now, so doing more of that stuff won't strain your finances.

Of course, the specific things may be hard to manage--there are things you can do when you're living in a garret on the Left Bank that just aren't practical if you're living in a suburban split-level. But the specifics aren't so important as the characteristics. And you wouldn't want to repeat the specifics anyway--you've already done that.

At the next level, start making more fundamental changes to your life. If the work you do isn't important, look for new work. Look around your current workplace for work that's worth doing and see if you can't arrange to do more of it. If there's no important work going on there, look around for places where there is. In any case, look for important work that you can do regardless of your job--volunteer work, artistic work, household work, etc.

Some of these changes may take a long time, but this is one of the cases where even small incremental changes are worth making. If what sucks about your life now compared to when it was great is that you're not in control of how you spend your time, take control of one hour a week--anybody who's not a prisoner can do that.

If your problem is that your work is not respected by your peers, start by looking at where the problem is. If it's in the quality of your work, then you can work on improving your skills. On the other hand, if it's because your so-called peers are a bunch of sneering jerks, look for new peers.

Over time, you can make quite big changes--new job, new career, new home, new school, new course of study, new skills, new friends, new colleagues. If the ones you have now don't remind you of the ones you had during the best times of your life, start making changes. Start making these times more like those times.

Two kinds of balance

A lot of the best of times is a matter of balance. You want the right amount of responsibility, not too much. You want enough collaboration for the team to succeed, but enough solitude as well. You want to strike a balance between thinking and doing.

Besides that, though, often the best times in your life are best because they're a change that gives you much more of what was lacking in your life. A vacation is great because it gives you leisure that was lacking. Your first job is great because it gives you money that was lacking.

Sometimes you can find a perfect balance--just the right amount of leisure in your everyday life such that you never feel a need for a vacation. Other times, though, a series of changes is better than trying to find a single perfect spot. Serious runners don't try to find the one perfect workout and then do it every day. Instead, they mix it up. One day a week they do a long run. Three or four days later they do a fast run. In between they schedule short and medium runs or rest days, to give them time to recover. In some aspects, maybe the best of times will always be like this--only best for a while, after which you need to move on to something different. That's okay.

Trying to engineer your life would be tough, which is why I recommend reverse engineering. Working from first principles about what makes a great life would be possible, but seems problematic in many ways. Fortunately, everybody has a time in their life that was the best so far. Use that as a model. You don't need to be a slave to it--if the best time of you life so far was high school you can probably do a lot better now--but it can show you one example of how to put things together to make a great life.

Reverse engineer your way to saying that "right now" is the best time of your life.

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Guest's picture

I agree. Like a baseball pitcher who tries to repeat his motion to be consistent, repeating your actions from a more successful or happier time in your life can make you more successful and/or happy. Why stay in the negative when you can reach back for something that has been proven to work? Nice post.

Guest's picture

Reverse engineering other people's success is a way to get something that you haven't had yet. Study the habits of someone who is doing what you want to do. It's a lot faster than trying to reinvent the wheel.

Philip Brewer's picture


Good idea.  Everybody talks about learning from the mistakes of others and how few people do it.  Learning from other's successes is just as useful and perhaps even rarer.

Guest's picture

I've actually been working on doing this exact thing for some time now. I've learned a lot about what the kinds of things that make me happy. I've been trying increasingly focus my life around these kinds of experiences. I will admit to struggling with incorporating my findings into my everyday career.

One of the points you hit head on was about being optimally challenged. If you get into this zone you are much more likely to experience flow rather than boredom or frustration.

One point I don't agree with was the comment about being a part of a team. Some people really function well as members of a team and some are better off as independent agents. The trick is figuring out how you work best.

If you are trying to do this I would also recommend reading a book by Martin Seligman called Authentic Happiness which outlines 24 different character strengths. The idea being that if you can shift your life towards your biggest character strengths that you'll be happier.

Philip Brewer's picture

@Save Buy Live:

Solo versus group efforts are also part of a continuum, just like all the rest.  Everybody has their own optimal point.  (Or, more likely, everyone has different optimal points over the course of their life.  Plus, most people probably benefit from shifts--working with a group for a time and then working alone for a time.)

Thanks for the suggestion about Authentic Happiness: Using the New Positive Psychology to Realize Your Potential for Lasting Fulfillment. It looks interesting. I'll check it out.

Guest's picture

Great Article Phillip, I agree. Your readers will also benefit from "A Tale of Today" at

Guest's picture

I've tweeted this article-much to weigh here, particularly for those of us who have been "blessed" with unemployment!

Guest's picture

Great post! I always try to think of the good times of the past as a warm-up or practice for the really good stuff to come.

lghbob's picture

We missed on a few of your points, but overall, I think we pretty much did reverse engineer our lives.
Living in the Adirondaks, being a forty-sixer, and canoeing the Chain of Lakes, were original priorities, second to going back to live on the Vineyard. Both were out of our financial range, so we settled on Florida, and that worked out great.

Some of our choices were subconscious, like avoiding schedules and standing in line for anything at all.

But, yes... summer up north, winter in Florida allows for year round outside. Living on a lake, both places... Not expensive living, but lakes and boats, and "outside".

Volunteering on a personal level. Not part of a formal team, but one on one help... Teaching - personal and on-line.

Staying in intellectually stimulating environment. (didn't make the college-town ideal, but close enough).

Successfully avoided the unpleasant parts of the working life, like commutes into Chicago, hop-scotching the US by air, and anything that remotely resembles vertical loading.

We've already had 20 years of happy retirement on a tight budget, and have no plans to change very much about our lives.

It wasn't automatic, though... deciding to give up a growing business was not a simple decision. Always wonder what life might have been like.

Perspective- Friends and colleagues from the working world chose to stay in the game, and waited to age 65 (7 years ago) to retire. To each his own. Their world travel, expensive cars and homes are satisfying to them, and I applaud their determination and hard work. Our extra 13 years of freedom from work and opportunity to pursue out interests was our sense of fulfillment and I suppose success.

We didn't have a plan, per se, but worked to get as much as we could of what we liked, and equally to avoid that part of what we didn't like.

In a way, I wish we had started earlier... picking the parts of life that make happy. Might have saved more money, changed to more rewarding jobs... but all in all, even without a early plan, we built our lives so that we have no regrets. Life is good.

my opinion only

Fred Lee's picture
Fred Lee

We think a lot about this idea of optimizing your life, but more so from the POV of living more in the moment. This would entail less nostalgia as well as minimizing fretting over the future. It's very difficult to do, especially with the world the way it is, and especially with kids.

We look to the past less as a blueprint for the life we want to live, but more as a source of knowledge from the lessons we've learned that help shape the values we hold dear which will ultimately go to shape what we are looking for in life.

Simplifying our lives in terms of money and consumer culture are a big part of it. That's why we live in the countryside in Vermont. That is not to say that it is easy, it's hard work cutting firewood and tending the garden and all that good stuff, but there is someting to be said for being more directly responsible to what impacts your life (i.e., food, heat, shelter) as opposed to paying someone else to provide you with it.

Sure, it's not for everyone. In fact, it's probably not for most people, but it sure fits us well. And with direction that the world is going, it may be the wave of the future.

Carlos Portocarrero's picture

Awesome post. I have had a post on a few months I spent in Paris and how fantastic it was, then I was going to break down the things about it that made me so happy and try to recreate them today.

Things like not having a TV, hanging out with different people, and speaking a different language. You, sir, have beaten me to the punch.

Well done!

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Guest's picture

I have been following the YMOYL plan for about 5 years, and I will be stepping out of the rat race in 11 weeks at age 40. I feel a little nervous about the transition, but doing this exercise really gives me hope that I can engineer a truly satisfying life. I am reading all your old posts now. They seem to be the words I need to hear to hear right now. Thank you.

Philip Brewer's picture

Thanks for the kind words! And good luck!