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The Most Important Piece of Career Advice You Probably Never Heard

Some Advice for the RoadGraduation

I’m leaving this afternoon to attend a college graduation: my second in three weeks. As you might imagine, graduating is on my mind, and, I would guess, on many of your minds as well. To celebrate the season I thought I would turn my attention to some advice for finding your way after college.

I want to share with you the unique law I use to guide my life. It’s a twist on the standard graduation inducements, but it seems, from my limited experience, to work the best of the various strategies I’ve watched my peers try on for size in their first years out of college.

The advice goes like this:

Fix the lifestyle you want. Then work backwards from there.

That’s it. Notice, I’m not talking about “avoiding taking yourself to seriously” or “always finding ways to give back.” I didn’t mention “the importance of a sense or humor” or why you need to “follow your passion, not money.” These are all reasonable words of wisdom, but they don’t necessarily direct you to a life that you’re happy to live.

My advice does.

Defining Lifestyle

What do I mean by lifestyle? Roughly speaking: a detailed feel for what your day to day existence would be like. Some questions to consider when imagining an ideal lifestyle:

  • How much control do I have over my schedule?
  • What’s the intensity level of my job?
  • What’s the importance of what I do?
  • What’s the prestige level?
  • What type of work?
  • Where do I live?
  • What’s my social life like?
  • What’s my work life balance?
  • What’s my family like?
  • How do other people think of me?
  • What am I known for?

Using these types of questions to guide you, construct an image in your mind about the ideal future you. Notice, specific jobs don’t need to enter the equation. They can if they help you visualize, but they aren’t necessary. Add little details. Really get a sense for what this lifestyle would feel like. If the image makes you happy and gets you excited about the possibilities for your future, then you’ve hit on a good match.

Example Lifestyles

There exists an infinite variety of possible lifestyles. Here are just a few examples:

  • The Power Broker: You live in a big city in a nice apartment. You climbed the ladder fast in a difficult business. You wield power. You’re good at what you do. You’re well respected. Your job is intense but you are super-organized so it doesn’t drive you crazy. You’re surrounded by good, loyal friends, and when you have fun, you have fun hard.
  • The Serial Entrepreneur: You live in a nice San Francisco townhouse. You’ve started several businesses. Some more successful than others. You tend to alternate between an intense year or two growing a business followed by some extended time off for intense relaxation. You’ve got a network of good friends across the country and a bar down the street that you visit every Friday night to catch-up with your closest buddies. You use your off time to develop extreme hobbies and indulge in grand, hopelessly ambitious and wildly fun projects.
  • The Virtual Voyager: You live in your dream house in a cozy community-oriented town, surrounded by natural beauty. You work virtually for several technology companies; setting your own hours. Three or four light days a week is enough to take care of your expenses. You and your family spend a lot of time outdoors, barbecuing with the neighbors, and, in general, enjoying small town life. You travel a lot for the sheer adventure of it.

Working Backwards

Once you’ve developed a detailed, visceral sense for your ideal lifestyle, use this image to guide your early career decisions. It’s a rough guide, to be sure, but it can still prove surprisingly useful.

Imagine, for example, that you’re faced with two options as graduation approaches. One is an elite project manager position at Microsoft and the other is acceptance to some good computer science graduate schools. Both are interesting and challenging. What do you choose? The power broker would go for the Microsoft position. The serial entrepreneur, on the other hand, would go for grad school — a perfect place to develop her first marketable technology.

The Power of Lifestyle-Centric Career Planning

Starting with a dream lifestyle — as oppose to a dream job — opens up more creativity. When thinking only about jobs, you’ll find yourself considering the same artificially-narrow menu of options troubled over by most talented college grads (banking, consulting, law, non-profit…) A lifestyle, on the other hand, provides much more flexibility — letting you discover potential paths previously hidden from your planning process.

The main advantage, however, is that, in the end, the whole point of worrying about your career is because you want to feel good about your life. By cutting to the bottom-line — what would make me feel best? — and then working backward from this answer, you are maximizing your odds that you’ll actually get somewhere worth going.

As with any graduation season advice, take this with a grain of salt. This is what I have seen work, but it doesn’t mean it’s the only thing that will. It can’t hurt, however, to take a moment to ask yourself: what lifestyle would suit me best?

You might be surprised where the answer leads you.

76 thoughts on “The Most Important Piece of Career Advice You Probably Never Heard”

  1. I think this is by far one of the most useful thought I’ve ever come across. It’s much more than the usual graduation sentiments, and is easily applicable to anyone in the midst of a major change. I think I’m going to sit down and try to think this through this weekend. See if I’m on the path I want to be on.

    Thanks Cal! As always, your incredibly insightful.

  2. I think this is some great advice! We often stumble along in life going wherever we are led. One day we look up and wonder how we got to where we are. Often, people find themselves buried in a life that they hate, but with so much responsibility it is almost impossible to change. Your approach may help people avoid this type of situation. Great thoughts!

  3. Totally Dugg this. Probably some of the best advice, and perfectly timed advice across any level. You must have read my mind, just the post I was looking for! Good one Cal!

  4. Why wait until you graduate 🙂 Start exploring different lifestyles while you’re in school and still have control over your schedule.

  5. @Jeff:

    I think “stumbling” is a great metaphor for a standard career path. When every decision is passed only though a “is this impressive?” filter, the ultimate destination may be far from optimal.

  6. very interesting. This article is for the little bitches out there that have a low self esteem and can’t secure the position they want because they are afraid of rejection. Money is the key to happiness people. If you want to be successfull (and by successful I mean live a meaningful life) chase money and network with those who are well connected to money. The more you have the more content you are and the better you feel about yourself. Dont listen to any of the pikers that tell you otherwise. They just don’t have the skills or pedigree to attain their goals and threfore must take pride in there shortcomings so as not to feel bad about their past and future inevitable failures.

  7. @Gman:

    Having lots of money and a high-speed lifestyle is a perfectly valid lifestyle to choose. Again, the focus is on starting not with a specific job but with what you want your life to be like. Though many might like the path you describe, others, I would assume, aren’t that interested in being the type of person who uses the word “pikers” non-ironically.

  8. Cal —

    I’ve been reading your blog avidly — great stuff!

    I think the lifestyle design idea is phenomenal. I’m at a crossroads and deciding what to do next with my life. I started college late and recently graduated from an Ivy League university in the US. I am considering several career paths and have done your design exercise for all of them. My issue is that I am torn between two things: 1) a “bohemian” type lifestyle in which I travel the world cheaply, learn languages, and spend a lot of time exploring other cultures 2) an “overachiever” type lifestyle in which I use my fancy Ivy education and job offer from a famous consulting firm to get ahead.

    I don’t really care that much about material possessions (the big house, car, etc.), but I do like to have an impact on the world, and want to have the credentials and experience that will make people take me seriously.

    I have grad school admission to a top business school (I did some business things before college) and am also considering law school. I want to have an impact, and all of the people I know who do this are “in the system”. I know that you don’t need fancy degrees to do so — successful bloggers are just one proof of this –but it does help to give credibility and open doors.

    So, I’m wondering how I choose among these career paths, but, more fundamentally, how to choose between these two impulses, which are like a split personality: the bohemian, non-stuff-embracing, traveling me and the overachiever, change-the-world, ego-motivated me.

    What do you do when your lifestyle goals conflict with each other? How do you reconcile them? How do you evaluate them?

  9. What do you do when your lifestyle goals conflict with each other? How do you reconcile them? How do you evaluate them?

    Can you combine them? Presumably vagabonding can be a source of experience that can inform efforts to change the world in a more profound way.

  10. Excellent post. I really like your concept of aiming for your dream lifestyle instead of your dream job. Of course there are different approaches that work best for different people but this is one approach I think many people will be able to relate to.

  11. cal you are so insightful
    my ex-girlfriend is the total power broker type
    while i have been struggling to decide how to choose my medical specialty – because i tend to want a balanced life
    your points have helped me see it clearly~

  12. Thank you for this very inspiring article. I’ve been struggling very hard to try to find “my passion” as everybody else seem to think that it’s the only way to a fulfilled life, but this motto has never made any sense to me since not only this advice only allow a narrow panel of options but also, what about people like me who do NOT have a passion. I do have hobbies and interests but does that mean I want to make them my job?! Hell, no! People seem to think that we are born with a passion and it’s up to oneself to discover it, and if one hasn’t found it, it’s only because we haven’t tried hard enough. These advices have wasted my time and made me helpless as I still haven’t found my passion. I am very grateful for your insight brought me hope and expanded the possibilities of my future.

  13. So very helpful, thank you so much for sharing what you’ve figured out.

    I just want to add that it’s OK for one’s perfect lifestyle to be something humble. For example, to do good, honest, enjoyable work with similarly good-hearted people, to work only during the week and not at all at night so that you have time to love and care for your family and yourself, and to make enough money to be self supporting, to pursue hobbies, and *to have enough to give to the poor*.

    When I gave up my resentments and saw that I stood to gain much more from orienting my work life around giving back what Life had so generously given me, I lost my obsession with what I hadn’t done or had lost and became able to do just what you suggest: craft a life that I wanted to live and then find work that fit the new plan. Amazingly, that work turned out to be just about what I was doing before. How grateful I am for new eyes!

  14. Insightful stuff. But I have one question though. How would I know what kind of lifestyle I want if I have not experienced it? I am currently in my fifth year of working and have recently moved division within the same company. Only after the switch did I experience small changes (not strictly work-related) that makes my current job more enjoyable. I now have greater influence over my own work output, my colleagues are friendlier which makes office time fun, and my hours are shorter than before. Although these factors seem like an obvious choice in envisioning ‘my future lifestyle’, I wouldn’t have picked these factors before had I not experienced and enjoyed it now. If you ask me five years ago what my ideal lifestyle is, my priorities would involve money, moving up the ladder and gaining recognition. I’m guessing the same will appear in the top five priorities of most graduates. So is it possible to really imagine my ideal lifestyle without first going through life and experiencing it?

  15. I graduated with a Doctor’s degree in Veterinary Medicine 20 years ago – from another country. Before I came to the US, I knew I don’t want to practice in a clinical setting. So I search for another degree via “follow your passion” mantra for 10 years, I even hired an overpriced career and life coach. I knew there’s something wrong about this philosophy, so I started to research on what happened to people who followed their passions both from internet and friends & acquaintances- not a positive result. The only good thing that came out of it was finding a CNN report about Cal Newports book. It was an aha moment. Dr. Cal Newport ideas resonates with my experience especially where I work (for seven years now). People who work longer in the company are the first one to defend how good the company is when somebody attack it. Also the longer they work at the company, the higher the age of their retirement. These are only observations not research. Well, I wish Dr Newport was born 10 years earlier.

  16. Being at a crossroad on my career path, this advice has come at the best time. I have a belief that I (and anyone who applies himself) can be successful in doing anything. My concern over the past month has been to pick the right one that resonates with me.

    To “Fix the lifestyle you want. Then work backwards from there” falls in line with Steve Covey’s effectiveness habit of beginning with the end in mind.

    Applying this advice in making my career decision may not lift the uncertainty that makes moving forward so uncomfortable but moving with an ideal end of an enriching lifestyle in mind is a refreshing perspective.

    Thanks Cal for all the insights for provide on this platform.

  17. The quote: “What do I mean by lifestyle? Roughly speaking: a detailed feel for what your day to day existence would be like.”

    While I agree with the above context, the questions that follow leave some key questions out:
    How do I pay my bills?
    Where do I live? (I already know where I live) Listed above.
    Where do I want to live? (yes one needs to have a choice)
    How do I contribute financially to other causes in society when I want to do so? etc…

    If you want “social sympathy” then by all means, settle for less.

    Let’s be honest with ourselves. If you choose a lifestyle that’s “easy peasy”, you will suffer in your day to day life. A bit of discomfort will not hurt.
    I’m currently working on/reviewing Deep Work by Cal and I find the book to be great so far. I like the book and it’s taking me a while to do the Deep work as a habit.

    I find that I need to “push myself” through a discomfort level to get the kind of lifestyle that I want which unfortunately Cal labels as “ego metrics — “what pays the most?””.
    I used to be in construction engineering and switched over to computer science/engineering.
    It was very tough but I never gave up. Today, I’m in the computer environment and glad I made the switch. I could say the same in the direction to Health care and others that pay more.

    What I found out to be a solution for me (and for others since I learnt from some folks) and continues to be are:
    1. Know yourself – who are you? what makes you tick? Are introvert or extrovert? Are you willing to switch from intro to extro or vice versa. Deep work is a lot of intro stuff. And yes Virginia, it can be done!
    2. Learn Self Awareness, your Emotions(critical) and Mindfulness Meditation (How do you react to events that occur to you?). Our interpretation to some of the events that happens to us is in my opinion what’s killing a lot of us – in the skills we are capable of creating and enjoying in life.
    3. If you truly can perform the above two steps, talk to folks in the field you want to go, there is a higher probability to make it. I have done it and others have too.

    As a brother of mine usually quips “Money is Not everything BUT Money is Next to everything.”

    • “While I agree with the above context, the questions that follow leave some key questions out:”
      should have read:
      While I agree with the above context, the questions above leave some key questions out:

      Sorry for the hurry…in posting.

  18. Thank you Cal, I defientely classify under the Serial Entrepreneur and I love it. It is true about the choices we make. What’s more important is knowing and being aware of those choices.

  19. The funny thing is I never would have thought that’s what I would end up doing. But every action pushed me forth to become who I am today. So working backwards I now realize would be to realize if there is a new lifestyle I want to live then I would work my way to achieving that life style

  20. What a load of BS. Most people’s “ideal lifestyle” doesn’t feature paid work – we do that only get the money to live or to assuage our fears for the future.
    So, when.we follow this process and honestly set our ideal as living in a nice house, pursuing.our interests, and being with friends and family in a nice neighborhood bit without the tedium of paid work, where does that leave our career choices?

    • Exactly what everyone misses. “Attainable” must replace “ideal.” What is attainable, what is within one’s grasp, must be rationalized. It’s okay to dream, maybe even good to dream; but we shouldn’t expect our dreams to realistically lay the foundation for our future. Visions don’t correlate to what is likely, or probably, to happen. Unless you’re a prophet or something.

  21. Hi Cal,

    This was a really interesting read and a useful tool for thinking about career. I found this after having read So Good a couple of times over the years and noticed that this concept isn’t heavily featured in that book. Is that because of the scope of the book or because you changed your thinking on this? I’ve struggled to implement So Good and in part that’s due to a lack of why. This is a very useful way to get at the Why (similar the the Future Authoring Program) and would be useful as a precursor to So Good.

    Keep up the good work,

  22. A fantastic article. My ideal lifestyle is actually very attainable: read loads of books, write loads of books, play the piano, and do art. So I just need a job that buys me the time to do all of the above.

  23. I’m 65, thinking about using this method to plan my next 5 year sprint to 70. I’m not done with things yet, not ready to stop and sit. Does it still apply if I’m not 20ish?


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