How Do You Make Life-Changing Decisions?

April 3, 2012

First, you get rid of the notion that anything about your life is really at stake. Whatever happens, you’ll be fine. You’re not deciding whether to do opt for chemo or not.

That is to say: calm down. We, the young and ambitious, deal almost exclusively with rich white people problems. We’re not going to starve if we make the wrong decision.* There is very little we can’t undo.

Of course, that doesn’t make life-changing decision any less intimidating or take away the fact that the adults in our lives did next to nothing in the way of preparing us. I think that’s why since I dropped out of school (and wrote about it as it was happening) people have been coming to me as though I have some special insight on making these kinds of calls. Since I did it then and have done it several times since, they think I know the secret. I don’t, but I do have some tricks.

When I get these emails I almost always ignore the specific details and respond with few simple questions. Stuff like: “What’s the absolute worst thing that could happen?” “What would you miss out on if you did it?” “Are you fighting for a piece of a shrinking dying industry or are you getting something whose value will hold up over time?” I never tell them what to do. I just pose questions.

These are no rhetorical questions, though I am sure they seem that way to someone just looking for advice. I intend for the person to answer them. Think about like a math equation for a second. It seems like a jumble of symbols and unknowns at first, but when you stop, breathe and break it down, the process basically takes care of itself. Isolate the variables, solve for them and all that is left is your answer.

Answer the questions and the right choice becomes clear.

This strategy gives you the single most important tactic when you’re trying to make life-changing decisions:

Get information, not advice. See most peopleno matter how wise or successfulgive horrible advice. They’ll send you astray. So don’t ask for advice. Ask them for information that you can translate into advice.

Isolate the various issues that will influence your decision and ask then people about that. By zeroing in on specifics rather than the big picture, you avoid the trap of their (distorted) picture. Simplify your decision into [If this] then [x] or [If that] then [y]. Then use the smart people in your life to help solve for the variables.

It’s the difference between asking: “What should I do?” and “Do you know anyone who ran into problems taking some time off from school?” To me, this difference was the world. I asked the latter question to someone when I was dropping out and their answer was brilliant. ‘Problems?’ he said, ‘I got really sick when I was in college and had to spend a year in the hospital. Do you think that matters at all to anyone 20 years later?’

So try it: What is the worst thing that can happen? Well, it could cost me some money. Ok, well money is replaceable so that’s a stupid reason not to do something with so much potential upside. Is this a once in a lifetime opportunity? Yes. Really, never again? I don’t know… Then you haven’t thought about this enough. And so and so on.

After that, this is what else is important:

-Think about where you want to go, back out your decisions from there. Let’s say you want to be a politician way down the line. Well, what does the biography of a politician look like? Probably some military service, success in the private sector, multiple degrees, clean private life, good connections, rich benefactors, a public profile, one or two key (untouchable) stances, sense of style, etc. Ok, now when you make decisions all you have to do is ask yourself: Does this help me check off any of those boxes? If it doesn’t, it’s probably not the right thing to do.

-Remember to consider opportunity costs.

-“Enter Action With Boldness” and sometimes, you may have “Act Before You Are Ready”

-It doesn’t matter how much other people ‘get’ you, they’ll never fully understand your aspirations so don’t go around expecting them to. It’s too hard for them to see past their own experiences. Prepare to be misunderstood, both when you ask for advice and when you finally take action.

-Scared about making the wrong choice? You won’t ever know if you did. Cognitive dissonance won’t let you.

-Strategy is a matter of options. Generally, the aim is to act in a way that leaves as many possible options open as possible (remember, opportunity costs). Keep this in mind as you make your decision. What gives me the most options? What gives me the most freedom and creates the most opportunities? Do not discount the things you do not yet know are important.

-Books. Books. Books. People have been doing [whatever it is you’re deciding about] for a while now. They’ve been moving West, leaving school, investing their savings, getting dumped or filing for divorce, starting businesses, quitting their jobs, fighting, dying and fucking for thousands of years. This is all written down, often in the first person. Read it. Stop pretending you’re breaking new ground.

Finally, don’t feel guilty for asking for help. There is NOT A CHANCE that the successful people you know today didn’t rely on the successful people they knew in order to get where they are. That’s the cycle. It’s why I respond to these emails and do my best to walk people through it however I can. So if you don’t have anyone else to ask, you can also come to me as a last resort. You know where to find me.

 *When I made the decision to leave my life behind and write my book, I asked Tucker: “Is there anything I should be worried about when I’m doing this?” His answer: “Nothing about any of this should worry you. It’s all upside.”

Ryan Holiday

I'm a strategist for bestselling authors and billion dollar brands like American Apparel, Tucker Max and Robert Greene. My work has been used as case studies by Twitter, YouTube and Google and has been written about in AdAge, the New York Times, Gawker and Fast Company.

45 responses to How Do You Make Life-Changing Decisions?

  1. The only caveat is that you need to behave differently when people depend on you.
    Men provide. Period. If you’re providing – and in your 20’s – it sucks. Lower your nut. Be ruthless about it. Your options are reduced.

    • I disagree–your CONSIDERATIONS are certainly widened, but your options are only reduced if you choose for them to be.

      • Probably semantics. You have less luxury to indulge yourself. When young men get into a situation where the have kids/wives/mortgages, it’s a shitty start. You talked about it with the bridges people want you to cross…

        I liked this post a lot…and the item would be: is this decision making it hard for me to have flexibility in the future.

        • Yeah you’re right. I just added a new item

        • Speaking from the “wife and kids” side, the start need not be shitty if you aren’t trying to live the lifestyle television says you should live. My husband and I helped each other live our dreams, while parenting our child and loving each other. We stayed fluid and kept our debts low. Thirty-five years later, my change-junkie self is making huge another leap (leaving academia for a new career), and I can’t wait! You should see the look of shock and fear in people’s eyes when I tell them of my change. Why would anyone leave the state tit and strike out on one’s own?

          • Chris Mershon April 7, 2012 at 7:04 pm

            I have a family, a new mortgage and a few years left of my twenties. I waited seven years to buy my home even though I could have purchased it at any point during that time. I chose to wait because I was unwilling to sacrifice the freedom that I felt was required to grow my career. I waited several years to get married for the same reasons. Now that I am on the other side of those decisions I can say that the heaviest weight I feel is in the evolution of those decisions and not the decisions themselves. Homes are easily sold and my wife thrives on change as much as I do. However, the effect these things have is to starve the ambition that feeds on vertical career goals, power and influence. In my life these decisions have bred contentment not control.

  2. Ryan, do you smoke? Picture on top suggest the answer is “yes”

  3. I’m actually just going through something now and was going to email you. This pretty much gives me everything I was hoping to get from you

  4. Excellent post.

  5. Excellent post, Ryan. The part about books reminded me of what Cicero gives as advice in times of grief: others have gone through the same.

    I would also recommend Spencer Greenberg’s ‘Making Really Hard Decisions’ –

  6. Favorite post from a long-time reader.

  7. Ryan,

    This is a great post. I have been reading your stuff long before the “Tim Ferriss Effect” and have enjoyed almost every single one of them. This one particularly hits the spot because I am in a situation in life where I do need to make some life changing decisions. However, the more I think about it, the more I realize although it is an urgent matter at the moment, it is perhaps not such a big deal in the future. Excited to see how things pan out.

    Love the “Get information, not advice.” message. It is so true. That’s the kind of stuff I talk about on my blog, Fishing Buddha.

    Anyway, keep up the good work.


  8. I liked this post a lot. Two questions I had that have been dealing with recently.

    1) Do decisions about things like home ownership also fall in with the part where the worst case scenario is costing some money? You’ve spoken out against home ownership before as part of keeping as many options open as possible. Is this part of your advice geared more towards young/restless than people who have kids like Chris Johnson talked about above?

    2) Was there ever any sort of timewasting hobby (TV, video games, etc.) you struggled with moderating yourself from when you were starting off? I know if something is important you will make time for it. I’ve tried focusing on The 50th Law’s chapter on Mastery so far, but I struggle with taking the easy entertainment route instead of pushing myself as much as I should.

    Thanks for any advice you or others have.

    • 1) The worst case scenario of owning a house is not losing money, it’s losing mobility. I mention opportunity costs last in the posts. THAT’s the problem with buying a house. In many cases at least, not all obviously.

      2) All the time. We’re human right? Chances are if you’re reading this site the problem is not as bad as it sounds. We have to have distractions to survive, just do it in moderation.

    • To add a couple financial thoughts about home ownership, aside from the mobility question, which is primary:

      An argument can be made that financially, for many people, it is a net gain to rent instead of own. That argument will depend on the individual. But one should never assume that residential real estate is the default asset class.

      Some considerations are time horizon: can I wait 20 years to see a return on investment? If yes, maybe I want to buy stocks. Am I going back to school? Maybe I want to put my money in a house, as sometimes equity is not counted in financial aid. Do I think my profession is globalizing? Maybe I don’t want to buy real estate that currently gets its price bid up by the local job opportunities.

      The best way to evaluate this from a financial perspective is to enlist the assistance of a competent expert who has no conflict of interest, such as a flat-rate financial planner. NAPFA, for instance.

      • I would add that renting gives you the flexibility to downsize (decline in income, divorce, children leaving the family nest) or upsize (higher income, having children). If you buy real estate, nobody can predict what it will be worth 20 years from now or whether the neighborhood will change, certainly not a “competent expert”.

  9. “-Scared about making the wrong choice? You won’t ever know if you did. Cognitive dissonance won’t let you.”

    this is so spot-on, so subtly, deceivingly simple, so staring-at-you-in-the-face, and yet something we never consider

  10. I am pleased I ran across your web site on aol. Thanks for the sensible critique. My wife and me ended up being just getting ready to study about this. I will be very happy to see these fantastic details currently being shared freely out there.

  11. Know of any first person books on being dumped?

  12. Jesse Douglas June 13, 2012 at 4:22 am

    @Ryan have you ever heard about house swapping? I’ve known plenty of people that trades sign up to social networks or put ads on craigslist and have swapped houses with person, family, or whoever. If you’re open to this possibility then I I think it’s fair to say your mobility isn’t decreasing.

  13. Excellent post. Whenever people ask for advice I always try and give them a clear perspective, not advice.

  14. such a nice post.
    thanks for sharing this.

  15. I like your article and generally agree, having had many of these thoughts myself in the past. There are a few areas where I’m stuck on the logic though. I realize the money issue is a bit cliche, however in reality, I’ve not been able to let the issue go. While money is replaceable, it is not necessarily replaceable in the timeframe or amount that is needed to survive. And while spending money isn’t necessarily the problem, the possibility of forgoing income in pursuit of life change is a greater risk. As I do not have a safety net (or ability to build one without the life change I am seeking), failure literally means homelessness and starvation in my case, which I don’t think I’m willing to risk.

    The other issue I have is that while I know what I want to achieve, and have reverse engineered a potential path to get there, I realize there are huge gaps in my plan that I have not been able to find answers to. It appears that I simply don’t know what I don’t know, and other people in my life also don’t know. Its fine to say i want x, but unless you can figure out the path to get there, it is impossible to take appropriate action. In some cases that path is discoverable, in others it is unknowable, and acting anyway will lead you astray. Further, some of the things I do know are on that path, are nearly impossible for myself to achieve. While I do not use that term lightly, I do try to be realistic about my skill set, resources, and aptitude.

  16. Great article but I need more info that I could translate into advice…can you help me Ryan? I would greatly appreciate it.

  17. My first thought upon reading the first paragraph was, “God, I hope nobody came here to decide whether or not to ‘opt for chemo.'”

  18. Thank you for posting such an interesting article.
    Reading it was somehow inspirational.

    I am currently “trying” to make a life changing decision.
    However, I am unable to do so, simply because I cannot tolerate the feeling of “regret”.

    I genuinely feel like taking a step forward… however…
    I fear stepping into the deep bottomless hole that is awaiting me.

    I will be overwhelmed with regret, and regret is what keeps me chained down.

    I no longer see myself advancing in anything good; I am merely stumbling through my days without a purpose. I used to be passionate about what I do, but that well seemed to have dried up sooner than planned.

    I am in my mid-twenties, working a full-time job for a year and a half now. I am making pretty good money to support my parent and siblings. I just want to survive the coming 23 years and 9 months until I retire and have time to decide what I want to do with myself? <– This sounds much better in my head.

    If I make a reckless decision now, a lot of people that matter to me will be disappointment. Plus, if I do not succeed, I will be disappointment with me. I have very little faith succeeding in anything; therefore, I will remain frozen.

    Your article gave me hope, but that hope soon faded away by the end of it.
    I can still hope for a better life, but I am a coward that will not move forward.

    All the best to everyone that do take that step and move up!
    Maybe one day I will grow balls … lol

  19. This is such a good and useful post, I keep on coming back to it again and again. Ryan, if you wrote a book of life and career advice for young people (in the same general area as The Education of Millionaires) I would buy a copy for every single person I know.

  20. I am enjoying and gaining some good direction from these posts. My husband and I are grappling with a decision that needs to either move or stay in our present location/state. One thing I do not see addressed is the part concerning children. We have three and the vary greatly in ages. simply saying children are part of the decision making does not fully address the reality that they have a voice, emotions, dreams, and fears about moving and how it will affect them. This is our biggest hinderance to this decision.

    • I know exactly what you are going through. My husband was offered a job in another state. The job offers a significant pay increase and chance of advancements. We have 2 teenagers and making this decision obviously will affect them greatly. It’s so hard to know what is the right choice….ughhh, what to do, what to do?

  21. Dealing with a potential life decision: interview for a lower management job in a beach city for a dollar more. Meaning pick up and move quickly if I get this job. Feels like a positive opportunity, yesterday,just interviewing, but now I’m more hesitant.weighing the pros and cons about not liking my job, the area I’m in… It feels like a dilemma. And have to make a decision in a day.

  22. Just a suggestion to retrofit some of these past articles with Pinterest-worthy images. Sure, I can pin this with any of the graphics on the page, but none of them will grab the attention of other pinners in order to bring traffic back to your site.

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