4 Transformative ways to make more money

You are not going to make more money by focusing on income. That’s a way to make small, temporary change. You need to make big changes in your approach to your life in order to make big changes in your financial path. Here are four ways to do that.

1. Stop hoping people will pay you to do something good for the world.
You do not get paid to save the world. You get paid to compromise. There are no jobs where you get paid a living wage to learn and do good and live consistently with your values every second of the workday. Those are volunteer jobs. The farther you get from this all-encompassing goodness, the more you get paid.

The jobs that turn out really good usually come after years of doing very difficult things to get to that point. Take, for example, being a Nobel Prize-winning scientist. You spend ten years in school. Then you relocate all over the world to go to the best teaching spots you can get. You write grants and have no idea how much money you will have year to year. You do that for twenty years, then you get a Nobel Prize. If you are the luckiest scientist in the world that year.

And, while it’s true that if you like your work, you make more money, liking work doesn’t mean saving the world (or even just doing your favorite pastime) every day. It means contributing something that people around you value. The value is clear because they give you money to do it. And you make more money if you are doing things you’re good at. So look for the intersection of what you’re good at (there’s a long list) and what people pay for (relatively short list.)

2. Work harder on your marriage.
Divorce is a career issue because it’s really expensive. Do you make millions of dollars a year? Reliably? If the answer is no, then you will ruin your career if you get a divorce. Because you will have to support your spouse and kids in the same standard that you would have supported them had you not had the divorce. Which means that you will have to start earning a lot more money if you want to maintain a household for yourself at the same standard of living.

Divorce is extremely career limiting: You will not have the option of taking a big pay cut, because you will be responsible for child support based on the job you might not want. And you can’t stay in the job you’re good at, because that only supports one household and now you need to support two. So the best thing you can do for your career is to take time from the office to figure out how to make your marriage work. Otherwise, the type of job you are able to get will depend on the type of person your spouse is able to marry. And you better hope that person is really rich.

3. Stay on trend but not ahead of trends.
A great way to make money is to know the gap between what’s available and what people want. This is called trend spotting.  And successful product launches address market openings created by new trends. (The GAP, in fact, is named for the gap in the market between what young people wanted and what their parents wanted.) If you can see trends ahead of others, you can make a lot of money.

Being ahead of the curve is risky. I have found that even in the startup world I’ve not benefited from being way ahead of everyone. But I noticed that Matthew entered the grass-finished beef business with perfect timing. He saw the industry emerging in New York and Chicago, and then when restaurants in Wisconsin wanted grass-finished beef, he switched over his farm based on how people had tried it before him, and now he gets much higher prices for his beef in both Wisconsin and Chicago.

It’s best to watch the people who are first and then do what they do but with less risk. Which means there’s someone who is earlier than you. A leader. So many self-appointed leaders have no followers, so it’s really the first group of followers that make the movement; the bleeding edge is not as optimal a place to be as next to the bleeding edge.

Another way to think about it: people usually know when they’re falling behind, but too often people say it doesn’t apply to them. I remember this happened years ago when I wrote about workplace change:  job hopping creates stability, grad school is wasteful and being lost in one’s twenties is a sign of sanity. People told me “not in my industry”. But it’s every industry. And the people who most thought they were immune from these changes—lawyers and academics, for example—are in the industries changing the most.

4. Get good at choosing a boss.
When I coach people they often think they are depressed because they don’t like their work, but honestly, that’s rarely the case with depression. Recently published research shows that it’s the boss, not the workload, that causes depression at work. This is consistent with research Dan Pink presents in his book Drive that says that we are happy at work if we have a satisfactory level of control over what we’re doing, along with a feeling of competence. This workplace situation depends on your boss, though, because you need measurable goals that are challenging but not out of reach,  and it’s difficult for a boss to make those type of well-defined goals.

The way to pick a boss who can do that is to focus on reputation. A good boss will have a slew of people who will tell you how that boss has helped their career. The boss will also have influence with his or her boss so you know you’ll be working on projects that are important to the company. Too often people focus on the glamour factor of a new job. But you’ll have way more control over the trajectory of your career if you focus on working for people who care about mentoring you.

45 replies
  1. Jim
    Jim says:

    You’re right: divorce is expensive. Mine set my career back, but it didn’t ruin it.

    I made a deliberate decision to live more modestly post-divorce — I bought a smaller house in a lesser neighborhood, and I have owned nothing but used cars I could pay for outright. None of this has detracted one iota from my overall satisfaction with life.

    Where I live, who my ex marries has zero effect on how much child support I pay. It’s based almost entirely on the proportion of her income to mine. No matter if she marries a zillionaire; I pay the same amount.

    The place where the divorce has limited my career is that I’m not willing to live far away from my children, so until the youngest graduates high school (in 2017) I’m “stuck” living in my city. Fortunately, I like it here.

  2. brooklynchick
    brooklynchick says:

    Just to be contrary, I have to say I work for a nonprofit doing interesting work and I make six figures.

    The rest of your advice is spot on.

    • Carrie
      Carrie says:

      I’m glad to see someone has posted in regards to making money doing something good for the world. True there are a lot of people doing good for the world who don’t make much money, but partly I think it is due to personal choice to go into certain types of careers that don’t pay as much as well as partly the economy or society not valuing those jobs but opportunities are out there to make a decent income doing good for the world. Think of the new generation and the sharing communities coming about. Twenty years from now we may be operating according to a whole new financial paradigm that is more community-based and/or more equal in income distribution. There are all kinds of new, innovative ideas sprouting up and a lot of that is due to the accessibility of the Internet. Thank goodness for that!

    • Bob
      Bob says:

      But you’re only one out of how many…? Most people working in non-profits aren’t flush with cash. They get paid consistently lower than someone working for a for-profit.

      I mean, there are multi-billionaire artists too (as an example), but the average artist barely scrapes a living.

      • Carrie
        Carrie says:

        Good point, Bob. I think it might help to clarify what is meant by “making money” and “doing good for the world.” Everyone has their own definition for each. I don’t think it’s necessary to make six figures to do good for the world, or that you have to work for a nonprofit either. I work for a for-profit educational company where I feel I do work that is both good for the world as well as have a conservative, but liveable income.

  3. Lucy Chen
    Lucy Chen says:

    You’re so right, Penelope! The exact reason I left my first full-time job, which was at that time my dream job as a finance graduate, was because after restructuring, the new boss was causing me to feel quite depressed.

  4. Ryan Biddulph
    Ryan Biddulph says:

    Hi Penelope,

    1 is all about sowing. Few realize that you must work intelligently and persistently for quite a while to make more money.

    The sowing precedes the reaping. The working precedes the getting paid.

    Drill this concept into your mind, focus on your WHY, keep working smart, creating value, building your network of friends, and in due time, more money will flow in than you could dream of.

    I have traveled the world for the past 33 months, teaching people how to live the internet lifestyle. Writing these words from the jungles of India. It took me well over 2 years to build up my online businesses to do what I do today.

    Great share, thanks!


  5. rachel
    rachel says:

    What sucks is when you’ve been through all of the above, repeatedly, and you know it’s time to get out and pick a new career.

    In picking a new career you’re doing all of the above again, only it feels like you’re doing it for the very first time.

  6. Joy
    Joy says:

    While I don’t think divorce should be the first option, I think this is a close-minded assertion:
    “Divorce is extremely career limiting: You will not have the option of taking a big pay cut, because you will be responsible for child support based on the job you might not want. And you can’t stay in the job you’re good at, because that only supports one household and now you need to support two. So the best thing you can do for your career is to take time from the office to figure out how to make your marriage work. Otherwise, the type of job you are able to get will depend on the type of person your spouse is able to marry. And you better hope that person is really rich.”

    For two working professionals with similar earning potential and no kids, this really doesn’t apply. And I think it’s pretty silly in this day and age for anyone to hang their entire fortune on a spouse.

    • Jake
      Jake says:


      Currently around 80% of the women us will have a child during their life. For the majority of DINKs, the “no” will go away at some point. If DINKs have any marriage issues, they should either fix the issues or end the marriage before they have children.

      Bullet #2 could be subtitled: Be careful with whom you have children because it will affect the rest of your life.

      • Penelope Trunk
        Penelope Trunk says:

        Right. Sheryl Sandberg always says the person you marry will be your biggest career decision. But so few people date with that in mind. It blows me away. People think it’s mystery what their career will look like, but by the time you’re getting married – late 20s- it’s pretty clear who will have a big job and who won’t. Who doesn’t have a chance in hell of staying home with kids and who probably will. But most people don’t like hearing that it’s already clear. They like thinking the world is still open to them and then they think that they can’t pick a spouse as a career decision.


        • mh
          mh says:

          Mr. h approached dating with a marriage mindset, and it almost freaked me out and sent me away, because at the time I was not about to “settle down.”

          And yet there is something so persuasive about a person who is clear about marriage.

          Anyway, I *did* try to dump him, but it didn’t take. Been together 22 years, married 19, and yes, I started staying home the minute child #1 was born.

          So much clarity in a marriage when one person is the earner and the other person is the caretaker/caregiver. The breadwinner is free to commit fully to the marriage and the career, and the caretaker is free to commit fully to the marriage and the family.

  7. Darnell Jackson
    Darnell Jackson says:

    Good post Penelope,

    They don’t say it’s cheaper to keeper for no reason.

    This was also one of the biggest points in Donald Trumps book where he talks about how many billionaires take little to no risk in their investments but don’t think about the risk with person they’re married to.

  8. Sheila
    Sheila says:

    I could not agree more about point #4 – bad bosses can hold you back even after you’ve left that particular job.

    • Penelope Trunk
      Penelope Trunk says:

      So true! A bad boss is like anyone else in your life in that if you let them get under your skin they can change how you see yourself and it takes a long time to recuperate your formerly more clear vision of yourself.


      • Liz
        Liz says:

        I would love to read a post on bad boss recuperation. I’m in the throes of changing how I see myself after a bad graduate school advisor.

      • charlene
        charlene says:

        Totally love this post!!! It has opened by eyes especially on the bad boss section. I can now understand why I’ve been feeling so down about who I am and my job this last year. “bad boss” for sure.I’ve allowed it to go too far.

  9. Carrie
    Carrie says:

    I agree focusing on what you can contribute that creates value for others, or is already valued by others, is a practical way to determine where to focus your career efforts, but it’s not necessarily going to bring more money or happiness. From my personal experience, I have found developing good relationships with others to be most rewarding for me, and I make a decent income that I am satisfied with. I have endured earthquake shattering changes in my industry (education) and company in the past couple of years, and I am still doing well because I kept my focus on providing good service to others while also showcasing my best skills or skills I wanted to develop. I have had great bosses and not-so-great bosses. Aligning yourself with a good boss is only helpful as long as that person stays with the company. That good boss can be laid off or transferred. Work on developing a good relationship with your boss, but don’t depend on that sole relationship for your livelihood or happiness. I advise working on developing good relationships with EVERYONE you work with. This is going to go much farther than attaching yourself to “one” good boss. I have twelve years experience developing good relationships with my coworkers, who in turn have recommended me for high profile projects and promotions because they fully trusted my ability not only to do a good job, but to also be someone pleasant to work with. You CAN make a decent salary doing what you enjoy and helping people. I do. I find what I do more rewarding because of the extra effort I took to develop positive relationships with my colleagues. It took persistence and didn’t happen overnight for me, but I do know if you are consistent in your focus of treating others well and doing good work for them, over time they will respect you and that is just as rewarding as a pay raise. So when a promotion or new job becomes available, they will be more likely to choose you than someone they don’t know or trust.

  10. Allison H Zadrozny
    Allison H Zadrozny says:

    Penelope, I love your thoughts and links. Since I’m 25, a volleyball coach, in the middle of a career change (saying goodbye to teaching kids with Aspergers and getting into business), and recently married, it makes sense that I’d connect with the content – but I like your style most of all.

    These four points are exactly what I needed to read today. I’ve taken all of your career/general life advice to heart – my husband love your writing, too.

    So thank you.

  11. Larry Hochman
    Larry Hochman says:

    What a great list! Of course there are more, and I’d add get really good at self-promoting, which includes creating a posse that will promote you as well. But this was a really fun and profound read. Thanks, Penelope!

    • Carrie
      Carrie says:

      I agree, Larry, self-promotion and networking with people who will support and cheer you on are integral to moving ahead in your career. I spent many years working hard on projects that didn’t get noticed much but word got out about my good work and people skills, so within a couple years I was working on high profile projects with big teams of people due to my self-promotion and networking efforts. Some people don’t feel comfortable with self-promotion, but think of it has just simply letting people know your skills and services you provide that you most enjoy doing. It’s like matchmaking. Eventually you’ll meet someone in the company (or elsewhere) looking for exactly what you can offer.

  12. Elizabeth
    Elizabeth says:

    This can sound crass: “the type of job you are able to get will depend on the type of person your spouse is able to marry” but is very true.

    I would expand it to: “the options you have in life will depend on the person you marry”.

    Though my husband is ambivalent about his career, and his many career breaks mean he doesn’t earn the steady six-figure income he’d have otherwise, he brings other ‘assets’ to the table via his passport, which gives us options for our future I wouldn’t otherwise have. I never thought about it this way before until reading your article. But I suppose that was one aspect of his appeal for me when we met: that our future was richer together – emotionally, career- and lifestyle-wise – than on my own (though I was pretty happy being on my own when we met).

  13. Kurtz
    Kurtz says:

    I agree with you that in order to make money you need to do something that is valuable to your society. Let’s take that logic a little further. Does that extend to say, Nazi Germany? There were millions of Germans, not to mention people throughout Europe, that focused on providing “value” to the Nazis instead of working to make the world a better place. Thousands of Europeans enriched themselves by helping the Nazis murder 11 million people in concentration camps, not to mention the 60 million people that died in the war. Same thing in Stalin’s Russia, Pinochet’s Chile, Franco’s Spain and so on. Small minded people like you, Ms. Trunk, are the problem with the world. You don’t have any perspective or vision, all you can think about is making money and starting a “career.” People like you are too shortsighted to understand what’s is valuable in life or what society really needs.

    • karelys
      karelys says:

      This is ridiculous.

      Of course they were making the world a better place!

      It’s what they believed. Down to the core.

      The problem here is not that people believed “I am going to make money rather than make the world a better place.” Instead, they believed that they were making the world a better place but they were way off the mark.

      A lot of religious people believe that adopting a bunch of kids from Africa and China will make the the world a better place. Instead, they are perpetuating a horrible cycle that we’re seeing in the adoption world.

      You sound so smart and yet your post seems to lack so much common sense. It’s stuff like this that gets people in a black and white thinking pattern: do good for the world even though I’ll be poor, or be evil and make lots of money in the process.

  14. Sadya
    Sadya says:

    People dont leave their jobs, they leave their bosses.

    So I guess the challenge is to have enough insight into yourself, to recognize that you are a horrible boss.

  15. redrock
    redrock says:

    the Nobel prize is not a goal to have if you want to make money and get rich. It does not come with a huge sum of money, and most people who get it do not even care that much. The decision to live on a decent but not anything you could call “rich people” salary comes the moment one decides to pursue research in academia rather then becoming an entrepreneur or investor or ….

  16. Patrick
    Patrick says:

    Couldn’t agree more. Work is a balance between pleasure and compromise as is relationships.

    Although I’ve never been married I know how a bad relationship can have a huge impact on work performance, even if isn’t a financial drain the emotional impact can cause you to lose focus and have a detrimental affect on your ability to sustain your performance and thus lead to a potential decline in income.

    My heart goes out to those with kids and a wife that have to go through a divorce.

  17. Bettina
    Bettina says:

    I am currently looking for a new boss right now, and Penelope’s words ring true.

    How can one find out about a new boss’s reputation besides the obvious, like LinkedIn and personal recommendations?

  18. Jack
    Jack says:

    Couldn’t agree more, especially on #5. As I recently started a new job, I was reflecting on my new boss and comparing to some of the best bosses I’ve had over my career.

    I’m lucky in that I’ve had many more good to great bosses in the past, than bad ones, but it does make the competition pretty fierce for my current boss.

    Being a good boss is actually pretty easy to do, but it does take a persistent and systematic approach that many people lack the discipline to acquire when making that individual contributor to manager transition.

    Setting clear goals, protecting your team, leading by example, and listening more than talking will go a long way to improve the average manager.

  19. karelys
    karelys says:

    I’ve noticed how people tend to vilify capitalism. And they have only this idea of “doing good to the world” that is very narrow.

    If you look around and realize how pervasive generational poverty is, and how actually just giving to poor people for the sake of helping does more harm than good. It may make you feel good, but it’s no help to them in the long run and not that much help in the short run either.

    But instead, if you do something within the frames of capitalism and start showing people a reachable way to fend for themselves they will start believing in themselves. You will make money. The business will grow because there is need and enough revenue to keep it growing. It will give jobs to many and a really good reward to you for your effort.

  20. Doug
    Doug says:

    I make some extra cash by dressing up as Santa Claus for events and parties. The site www [dot] hellosantallc [dot] com helps because they have leads. They have a small referral program too. Won’t make me rich but extra is extra right?

  21. Coach Oz
    Coach Oz says:

    Love your first point Penelope. I think people find doing good for the world a lot easier after they have earn a steady paycheck. You can’t feed other people until you’ve fed yourself first.

    Coach Oz

  22. Delgada
    Delgada says:

    Divorce and single parenthood are statistical indicators in poverty, especially generational poverty. Very large factor.

    I am surprised there is arguement to this. Just ask a few guys who work second or third shift in any job. They have hours of stories if given the chance.

    Network with people, get to know them, be real. Then grow in wisdom from it.

  23. Derek
    Derek says:

    Great article! I might add- really, really think about the decision to have kids. Don’t just do it because it’s the next thing. Also, it gives you the option do make less but enjoy your work and split if you don’t like your boss :D

  24. ChrisH
    ChrisH says:

    Divorce will kill you financially. Most people marry for love without any understanding of the business side if being single or a single parent. It is incredibly hard to get ahead in this world as a single anything. Very rare.

    Agree that bad bosses are the root of many problems. The main thing being left out is that almost no one can ascertain whether their new boss is a jerk, incompetent or politically motivated careerist when they’re hired. Only people transferring intra-company would be able to gain those insights effectively, or, those people who spend a very large portion of their time being heavily networked. Neither of those conditions are the 80% rule, so the advice to avoid becomes somewhat obvious (and ineffective).

    What would be better would be a post about how to work out of a bad boss situation – and I’m talking about the ones who are the manipulative careerist pricks that like to use people like chess pieces, not the obvious ones like the idiots and easy hr offenders – but the ones who know the system and game it regularly.

  25. delgada
    delgada says:

    Fist pump to what Chris H said abt bosses. Yes, would appreciate perspective and strategy to road blocks like what he describes.

    Would like more in my war chest. Currently, I use weekly notification via email of my accomplishments, dedelicate and benevolent handling, careful and watch his chess move then respond.

    No one likes getting blind-sided, but there is a point where it just becomes the unexpected, then it is not personal and one can move forward much faster.

    I also only look at my current position as something as long term as the current deal, project, commitment. It is my responsibility to be clever and ready.

    Have you done one of these kind of posts before?

  26. Zeemo
    Zeemo says:

    This is such a great article and I could not agree more.

    Having seen my parents go through a divorce, I can definitely see how this can be a real drain on your bank account (especially when children are involved). And I had never really thought about my bosses being the reason I have hated so many of my past jobs – but now that I look back on it, I completely agree! They were all casual jobs whilst I was studying, so I couldn’t really be that picky.

  27. Bryan
    Bryan says:

    Great article. I appreciate the nuance of the first one (for we certainly can get paid, and paid well, for being of genuine service to the world, though you point this out) … and the second, work harder on your marriage?? If we only did that much we would be immensely happier regardless of how much money anyone made.

  28. Chris H
    Chris H says:

    Excellent post. You effectively addressed the issue of Gen Y passion and altruistic capitalism by cutting through all of the bs. The value of marriage and its consequences is a huge callout. No one seems to grasp that it is *nearly* impossible to achieve long term success in today’s world as a single person. Team work wins all scenarios, and starts with your own team first.

    I would add the following.

    All hiring is essentially based on risk management. When you chase aggressive income changes, you will inherently absorb more risk (Incl bad bosses who are way out of the league). If you haven’t accumulated the skills and experience to support the risk structure, you will most likely fail….badly.

    Be ruthless about expense management, downsize, and then downsize again. Set realistic expectations with yourself about what success looks and feels like, and prioritize your life goals. Try to focus on spending only on what is necessary, and not what you want.

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