How to Be More Generous

Hello friends and welcome back to Life Reimagined, a free weekly elixir designed to make you feel good and live better.

This week, we’re going to talk about how to make typically unpleasant life events more fun and some practices you can try to become more generous with money.

😩 I. Getting Unstuck

While preparing for a recent move from San Diego to San Francisco, I started to feel overwhelmed by everything that needed to be done. And I got to the point where even thinking about the move made me feel anxious and unsettled.

Tired of feeling bad about what was supposed to be a positive life change, I woke up one Saturday and tried a silly exercise to see if I could change my relationship with the move. I wrote two sentences in my planning document:

Moving is stressful, expensive, and hard. What if it were fun, affordable, and easy?

I spent the next hour thinking about how I could make everything that I had to do fun, affordable, and easy. Two months later, my wife and I moved. And while it was not the best experience of my life, it really wasn’t all that bad.

Thinking back on the experience, that hour I spent on a Saturday changed everything. I stopped thinking about the move as something that would be terrible and focused instead on how I could make it a decent experience.

And on the days I started to feel overwhelmed, I revisited my two-sentence reframe. It did not always solve the problem of the day, but it did get me into a productive mental state that got us to the finish line a lot more smoothly.

This technique may seem like positive-thinking, self-help babble soup, but it works and can make a lot of the typically unpleasant experiences of life a lot more enjoyable.

For example, let’s say you’re looking for a new job. Most people dread the process of updating their resumes, filling out applications, and interviewing.

I won’t claim that you can make these things entirely pleasant, but you could accept that you have to do them and spend an hour thinking about how to make the job search less of a drag. In fact, what if you could make it fun?

Perhaps you use the job hunt as an excuse to connect with strangers and learn about new careers you’re interested in. Or maybe you can use it as a way to spend time with a friend who’s also on the hunt. Or you can see it as an opportunity to find a dope role that gives meaning to your life and pays you well!

The key is figuring out the reframe that works for you.

And sure, you will still have to do all the tedious stuff that comes with interviewing for jobs, but in reframing the experience, you can avoid the unnecessary worry or dread that consumes most job searches.

So the next time you confront something that is bumming you out, like an unexpected illness or injury, a relocation, a breakup, or an annoying business problem, open up a blank document.

And ask yourself: How can I make this easier or more enjoyable?

💵 II. Dear Cal: How Can I Be More Generous?

In the first edition of Dear Cal, a Q&A series where I answer reader questions, we discussed how to make friends in a new city. This week, a reader asked me a question about changing their relationship with money.

Dear reader,

Your relationship with money has very little to do with the number in your bank account. This idea typically only resonates once you have some extra cash and see that you still feel pretty much the same as you did before.

When you’re strapped for cash, it’s hard to believe this. Money seems like the answer to all of your problems, and it is true that it is the answer to some of them. But once you have a small amount of savings, changing how you feel about money is a psychological exercise, not a financial one.

Money advice is hard because everyone’s relationship with money is so different and personal. How you feel about money is informed by your childhood, how your parents talked about money, the people you hang out with, and the narratives that you’ve absorbed from society.

Because everyone’s money psychology is so unique, there is no silver bullet solution for solving money problems. You and I could have the same money issue (e.g., a desire to be more generous), but the solution for both of us could look very different. Money gurus will tell you that there are universal answers, but they’re just trying to take a few of your dollars in exchange for their advice.

The truth is that the only way to change your relationship with money is to figure out what you want to change and experiment with different practices to see if you can move the ball in the direction you want to go.

So in the case of trying to be more generous, I’ll share a few of the low-stakes practices that have worked for me. There’s no guarantee that they’ll work for you, but even if they don’t, they may seed new ideas or get you thinking about the problem more deeply.

Create a generosity budget

A generosity budget is an amount of money that you allocate toward being generous. It’s like a travel budget, but instead of using it to go yachting in Croatia, you use it to be a more giving person. Let’s say it’s $1,000 this year.

How you spend this $1,000 is up to you. You can use it to take a friend out to dinner, do something nice for your parents, or whatever makes sense in your life.

I spend most of my generosity budget on having awesome experiences with friends and family, but you may want to use it to be more giving with strangers or to support organizations that work on causes you care about.

The point of the budget is to help build the muscle of being more generous. As you do that, you’ll probably find that being generous starts to feel easier for you and also comes with good feelings about how you’re using your money.

If this approach works, try increasing your generosity budget every year.

Do small things for strangers

Sometimes when I’m having a bad day, I do something nice for a stranger. I don’t do this because I’m a good person. It’s really a selfish act of giving that helps me feel better.

A classic and easy-to-do technique is to buy a coffee for the person behind you at a cafe. For $5, you can make someone’s day and feel good about it.

Once you do this a few times, you may find that giving in small amounts to strangers is a very accessible and fun form of being more generous. And if it’s fun and easy, you’ll likely do more of it.

Do something for yourself

I’ve met some people who will give their last penny to a stranger, but who can barely pay for a matcha latte for themselves without feeling guilty about indulging in something they don’t really need.

If you’ve worked hard, earned money, and have extra cash to spend, there is no law that requires you to give it all to charity or help other people while you continue to live like a college kid surviving on ramen. Part of having a healthy relationship with money is learning to use money as a tool to have more of what you want in life without all the guilt.

So if you're someone that's always focused on others to a fault or who constantly has guilt about buying “things you don’t need,” you may want to try being more generous with yourself.

Think about something you’ve really wanted to do but haven’t done because of some fear or shame you have about spending money.

It could be taking a solo trip to Japan, buying an overpriced t-shirt that you love, or hiring a cleaner who can free up some of the time you spend taking care of the house every Sunday.

Just pick something, and do it. You won’t become a bad person or a spendaholic or someone who is going to go broke due to lifestyle creep if you allow yourself to indulge in a couple of nice things.

When I first used this technique, the best thing I did was to allow myself to buy as many raspberries as I wanted. I grew up loving raspberries and not always being able to afford them, so now I buy as many as I want. I often eat an entire pack a day, and it makes me stupidly happy for $20 a week.

So dream up your version of the raspberry, and go get it.

Don’t wait until you have more money

No amount of money or success will make you feel ready to be more generous. Giving is a habit, and the only way to build that habit is to start today and continue to do it.

While it’s true that having more money can allow you to do more for others, you likely won’t end up being generous once you have more cash if you haven’t built the habit of being generous with less.

I’ve met plenty of people with $2,000 in their bank accounts who are far more generous than people with millions of dollars.

—

That’s it for this week’s Dear Cal. If you enjoyed it or have any additional tips for becoming more generous, let me know!

And if you want to submit a question for me to answer, you can fill out this form or reply directly to this email.

🧠 III. Something I’m Thinking About

This is a useful approach for both travel and most of daily life. Planning is important, but it’s fun to leave space for serendipity and to allow life to unfold more organically.

That's all for now. See you next Sunday.

— Cal

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