Motivation & Money: How to Find Your Carrot on a Stick

Are you getting overwhelmed by everything you’re supposed to be doing with your money? We should be doing so many things when it comes to money, right? We should have so much in the bank for an emergency, so much put toward retirement, so much invested, and on and on. Then there are the should nots on top of that – shouldn’t spend frivolously, shouldn’t carry a credit card balance month to month, shouldn’t default on loans. They are endless but as an adult, we should at least have our financial $hit together, right? But are all these shoulds weighing you down and making you miserable?

Certainly these shoulds are great words of wisdom but if you find them demoralizing, depressing and exhausting, then they won’t motivate you with your money habits if your actions haven’t changed already in response to them. In fact, they may demotivate you and actually impede your financial progress. Here’s why and what to do about it to win the money game.

Motivation Isn’t a Should

Back when I was trying to change my financial life from broke and over six figures in debt with student loans and credit card debt, I read every book I could get my hands on when it came to money but I also read on motivation and the habits of winners. That taught me about passion, ambition, vision and the truth about self-motivation that coaches rarely address. The real secret? Motivation is identifying your inner drives, not the financial shoulds that just make you feel stressed out.

Most people focus on “shoulds” when their fears and desires shape their actual behavior. Even though I write about money, it might surprise you to learn that I don’t actually love money. I’m not sitting around counting my dollars or scheming about how to be rich. Instead, I focus on how to maximize my personal freedom. That’s my true passion and driving force. I don’t like working for others, not having a say over my schedule or tasks and having to take orders from someone else. I’m very independent-minded and want to direct my own life – every minute of it, even if it’s just sleeping till noon and missing out on half the day. I also love travel and writing and dislike the thought of ever being on the financial edge like when I was homeless as a kid. To have the personal freedom I’m passionate about though requires financial freedom. That’s why I’m interested in money.

All these inner loves, fears and goals drive my motivation and got me financially free. Shoulds didn’t get me anywhere. I didn’t think to myself, I should have X amount in the bank or make X amount of money. Instead, I was like “how the hell do I get out of the rat race and live my life on my terms as much as possible?” Though I knew I needed roughly X amount in the bank, I focused on why I needed it and where it would take me, not on the number itself. This is a nuance in thinking but it made all the motivational difference. My dreams of travel and freedom and fears of poverty led me every step of the way to get my debt and budget under control, learn lucrative skills I could then use as income for investments and passive income, and then quit the rat race to live on my terms. There were no shoulds. These steps were more like “must dos” on the road to my actual goal.

The takeaway: Shoulds might poke and prod you but your real motivation comes from how you want to live your life – whether that’s retiring early, starting your own business, putting your kids through college, taking a dream vacation or what have you. Once you have the why or what figured out, motivation follows. Shoulds don’t motivate, they nag. How often have you seen anyone jump up with excitement for a task after being nagged? Right, you haven’t.

The Burning Passion

The trick is finding what you’re actually passionate about so that you naturally produce your own motivational fuel. We have a lot of so-so goals. By this, I mean goals that our hearts only feel so-so about, no matter how big, amazing, or even necessary those goals might be. Typically they turn into shoulds. Plenty of people want to lose weight for health reasons. Few do. Travel overseas is a common dream but something like only 40% of Americans actually have passports. Dreams and goals are great but they need passion behind them. “I should save money” won’t get you anywhere. Neither will, “I want to save money” if it’s not exciting you to act. If you’re not acting on it, you don’t actually “want” to do it. It’s a so-so priority and it’s not going to fuel you very far.

Our actions tell us what we truly love, not our thoughts or hopes or words. When we want to do something, we typically do it whether it is good or bad for us. The trick, is finding what our deepest desires and fears are that are helpful to us and stoke them like crazy so that we act on them in more constructive ways. For instance, I love reading and learning. However, reading the classics and historical non-fiction wasn’t getting me the bigger paycheck I needed to walk those Thai beaches like I wanted. Reading on self-development, business acumen, investment strategies, and non-stop Japanese manga and Japanese light novels educated me (learning Japanese tripled my income) and were interesting or fun in the meanwhile. I kept wanting to read those works and as I did, I developed the skills and knowledge that upped my net worth tremendously. Taking a habit and making it useful changed everything.

We all have habits and interests – and they can financially constructive or destructive. I have a friend who defaulted on her student loans despite over $900 extra a month in disposable income after all living expenses and bills were accounted for (including that loan payment). She loves going out with friends and getting mani/pedis and burns through cash on these activities. That’s fine but there are ways to organize around those loves. If nothing else, the way she goes through beauty products could make her pretty suited to a blog/YouTube channel on the stuff she uses. With time and dedication, she could probably start generating passive income from product recommendations, product sales, and how-to lessons, especially when paired with her love of writing and teaching. That way she could generate the income she needed to support activities outside her salary. And it would all revolve around things she loved doing already.

Here’s another example of using real drives to motivate a so-so goal. If you’re wanting to get in shape and save money but unmotivated, you could tie it to something else like my aunt did. She’s a very social creature and would go out with friends and wind up spending money. She also hates working out alone. She might be able to exercise alone for a week but soon loses steam and quits. When she merged social time with exercise, she was finally able to lose weight, stay in shape long-term and save money otherwise spent on dining out. She and her best friend worked out in the afternoon at her friend’s house for years, which meant more social time together but in a supportive and healthy way rather than going to the the local burger joint like they had been doing (and far less expensive). That’s how she motivated herself. Otherwise, the “I should work out” or “I need to exercise” or “I need to spend less” wouldn’t get done. Instead, the “I want to spend time with my friends and family” that is so important to her won out but in a constructive way that enabled otherwise so-so goals like exercise and spending.

These are just examples of taking interests and habits and making them financially useful. If you’re just making goals based on behaviors you should be doing and getting upset by not accomplishing them, take a moment to reflect on what it is you really want to do. Organize around that love or dream. If it’s go out with your friends three times a week, that’s fine if that’s what you love. Just organize your finances around that. Be like, “if I pay off that credit card and not carry a balance, that payment can now go toward nights out.” Or whatever it is that speaks to you. You’ll be far more motivated than if you tell yourself you should stay home and not spend the money. You’ll have better checklists too to help you live the life you want, not the one people think you should live. It’s really all about problem-solving around doing or obtaining the things you love or want without wrecking your life.

The takeaway: Tie goals you feel so-so about doing to your must haves in life. That aligns your passion and therefore your energy and focus to work on your behalf rather than against you.

Dreams, Not Checklists

Have you ever noticed that anytime you fixate on “what you should be doing” and lose sight of your underlying goals and dreams, your motivation flags and you start getting upset with your shortcomings, failures or how long it would take to reach your financial goals? In other words, you got DEMOTIVATED. This easily happens when staring at a wall of checklists for dreams or goals broken down into too many minute step-by-step goals.

Many motivation coaches and gurus love checklists. You have your daily goals checklists, your weekly goals checklists, your goals for the month and year, etc. These can certainly help us organize our finances. I love checking off items completed but will get overwhelmed with keeping up with them if they’re written down for the day, week, month and year. Many people will. Instead, I use them judiciously – like setting up five short-term goals to get me toward a big goal that I’m passionate about. Five is about as much as I can handle before I get so overwhelmed that I abandon everything. Maybe you’re the same way.

Checklists are tools, not ends in themselves. They’re certainly not mandatory and they’re definitely not one size fits all. They’re also hard to get excited about which is why it’s important to focus on what they’ll get you and why you’re doing them. Without a what or why, you won’t have the inspiration fueling you to complete that task.

When it came to getting on top of my $18,000 credit card debt (yes, I had this much), I had checklists that I loved ticking off – payments for each credit card (I had several), dates, and their amounts all counting down to zero. I loved making payments so that I could bomb away that debt and be that much closer to financial independence and walking the beaches of Thailand a free agent (which I did, less than 10 years later). That particular checklist was fun and I loved doing it. Would I have loved to spend the money elsewhere? Absolutely. That greater goal of travel and freedom, however, was so overwhelmingly a priority that the checklists got done and were fun in the process. It wasn’t a should but a “want to do” and that mental difference was everything.

The takeaway: Know your priorities and keep them front and center.


The secret of success is tapping your inner drives. No one can tell you what they are and how to tap them. It’s your life after all. How you want to live it is something only you really know. Not sure what you want? Look at what you’re already doing and how you’re spending your money or time. If you’re out with friends or family, you’re highly social and won’t want to do things that take away from that time. To accomplish financial goals or dreams, you’ll probably need to tie them into social time with family and friends (see these money hacks for social people). If you’re a workaholic, then you will likely want to tie your financial goals with your profession since then you’ll want to work on them. If you try to take time away from what you love, you’ll only shoot yourself in the foot and demotivate yourself.

We all have varying personalities and self-needs that have nothing to do with money but which invariably impact our finances. Someone who loves going out with friends will typically spend their money on activities or food and drink while someone who loves pampering themselves might spend the money on clothes, the latest tech toy or massages. The trick is finding ways to meet these inner needs in smart, less expensive ways – that or finding a means to make money off them.

Once you identify your inner needs, the money problem will be much easier to sort out and problem-solve. Will it be easy? No. But it’s probably one of the only ways to have lasting motivation. The great thing though is that once you find these answers, you can use this method again and again to create the self-motivation so many want but few obtain.

Like this article? Share it so that others learn these money secrets and start living their best lives now.


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