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Five Things To Do Now That Will Ensure You Don’t Regret Your Life When You’re 80

Life is a chain of difficult decisions: About love, about work, about money. How you approach these decisions in your 20s and 30s may make you happier later in life.

Decisions you make in your 20s and 30s can lead to regrets later in life; some advice.If there’s one thing I try to remind myself of everyday, it is this: The key to happiness – or as close to one as exists — is to live in the present moment.

Living for now means savoring a turkey sandwich rather than scarfing it down while checking our Facebook feed. It means taking the time to go for a walk – sans earbuds – and to hear the birds, feel the breeze and yes, even smell the roses. It means taking a boring job – whether it’s doing the dishes or writing a TPS report – and giving all of yourself to the task at hand.

Not least, living for now means letting worries about the future and past regrets pass like clouds through the skies of our consciousness.

This power of being present is the root of messages from ancient Eastern religions and new age gurus alike because it – along with choosing to live your life for other people rather than selfishly — might be the only two things that matter.

Life, wherever you are in it, can be difficult. These principals, the wisdom of ages teach us, make it possible to fill our cups with more contentment than pain.

How is it possible, then, to live a life of “no regrets”?

We often hear anecdotes about the regrets passed on to hospice workers at bedsides of the dying. “I wish I didn’t spend so much time at work” goes one. “I wish I forgave people” is another. “I wish I let myself be happy” is one more.

It’s impossible to avoid regrets altogether. We must frequently make choices with complicated tradeoffs. What if the job of a lifetime means ending a long-term relationship? One day, you may regret either decision, or at least ask “what if?”

In that case, we can acknowledge the regret is there but choose not to indulge it. Let it not cloud your consciousness.

But in some cases, is it possible to live in a way that minimizes regret? I think so. Especially when it comes to money and life in your 20s and 30s.

1. Don’t give up on the career of your dreams.

If you have a calling – to be a doctor, an artist, or even an archeologist — then you should do everything possible to follow that calling.

For one, not everybody is so lucky to even know what they want to do. Many of us stumble through life unsatisfied with most of our work, not even sure what our passion might be.

If you always wanted to try to make it as a musician or an actor or simply follow the path to a certain profession, you will likely regret it if you never try.

2. Don’t borrow more than you can repay in 20 years.

Unfortunately, following a calling requires money: tuition for school or cash to pay the bills while you ascend the ladder.

To a certain extent, it’s okay to borrow money for education that will further yourself on the path. Investing in yourself is still one of the best things you can do for building long-term wealth.

But you have to do it wisely.

Do you need to borrow $100,000 in student loans for a B.F.A. to be an artist? Probably not.

In a more pedestrian example, you might choose to work and go to school part-time while earning a Master’s Degree to change careers rather than borrowing more for living expenses while you go to school.

Obviously, you want to try to borrow as little possible when going back to school, but student loans are a necessity for most. Just think about what you’ll be repaying before you go.

Too often, I hear from readers in six-figure student loan debt for degrees that don’t lead to six-figure jobs. In these cases, they’ll be paying their student loans for most of their working years. That makes it extremely difficult to get ahead in life: To buy a home and save for retirement.

Likely, they will someday regret going into so much debt because it delays — or hampers altogether — other life goals.

3. After college, don’t stop making friends or reading books.

There are lots of great things about college, but I think the best has to be how easy it is to make new friends. Stack thousands of people the same age on top of each other who are all going to classes, meals and practices together, how can you not find people you like?

The other great thing about college is you’re forced to read books you might not pick up on your own. This exposes you to new ideas and challenges what you think you know.

But then we graduate and take up uninspiring entry-level jobs. Maybe we move back home with our parents, grab an apartment with a friend or two, or find some totally random roommate on Craigslist.

Suddenly our circles – both social and intellectual – become smaller, and it’s harder to grow them. You have to go out and find friends, you don’t just live on top of them. You have to make time to read, and you have to challenge yourself to find what’s worth reading.

Motivational speaker Charlie ‘Tremendous’ Jones was famous for saying: “Five years from today, you will be the same person that you are today, except for the books you read and the people you meet.”

4. Travel whenever you get the opportunity.

I get a lot of readers, many still very young, who are laser focused on FI (financial independence, also known as early retirement). Their goal, and it’s a good one, is to save enough money so that they can live off the interest and not have to work. Many are striving to do this by a very early age: 45, 35 even 30.

Although reaching financial independence at an early age is more achievable the more money you earn, many people how it’s possible on relatively modest incomes. Let’s say you earn $54,000 a year. If you save a third of that money, $1,500 a month, over 20 years, you’d have a little over $600K at 5 percent interest. If you retire at 42, you could theoretically withdraw 4 percent a year safely without touching your principal – just about $25,000 a year to live on.

Now, that lifestyle is very frugal. But as the FI crowd will tell you, it’s certainly possible. Millions of Americans in poverty live on less.

All it takes is a desire to sacrifice middle-class consumerism for that goal of financial independence.

I take a more balanced approach. I want financial independence, too, but I don’t want it so quickly that I’m willing to sacrifice enjoying certain things today. After all, any one of us could get hit by a bus tomorrow, so it’s silly to put off living completely while we save for the future.

And the prime example of this is travel. One of my biggest regrets about my 20s is that I didn’t travel more. I didn’t study abroad in college because I was worried about the cost. And the poor choices I made afterwards that got me into debt made it impossible to afford many cool trips through the rest of my 20s.

But here’s the thing: Traveling may get easier to afford as you get older, but it won’t get easier. If you are young, healthy and unattached, you can get out of work on a Friday and travel to a new place on a moment’s notice.

Plus, if you travel to a new country, you’re gaining cultural insights that will forever make you a more informed and compassionate person. I’ll stop short of recommending you go into debt just to travel, but you should find ways to travel while you’re young at any cost.

5. Design a lifestyle that leaves you money to save, but also some to spend.

Too often, we don’t look at our finances until we’re “behind the ball”. For example, we spend years living beyond our means, accumulating credit card debt, and only when the debt becomes unmanageable do we decide to make a budget.

Or maybe you manage to avoid overspending, but when you decide it’s time to save for retirement, you realize there isn’t much left to save without making major sacrifices in your monthly spending.

How does this happen?

Most of us don’t design our lifestyles with money in mind.

We make life decisions based on what we want without considering what we can afford. We choose the college that “feels right”, the career field we’re passionate about, a place to live that’s charming or in a desirable neighborhood.

Now I’m not saying to make all of your major life choices on money alone. Choosing a job solely for on the paycheck will likely lead to major regret.

But you can do this: Imagine what life will look like next year. In five years. In ten years.

What will you be doing? How much will you be earning? What kind of lifestyle will that allow you to live (and save a bit, too)?

Doing this exercise, you can decide how much you want to save, what you want to spend money on, and what income you’ll need to support that lifestyle. You can then pursue higher paying career (or side hustles) if having more money is important to you, or you can scale back your big expenses (like where you live and what you drive) to enjoy a lower-paying career without financial stress.

It’s impossible to avoid regret. Life is a chain of difficult decisions. Inevitably, we will choose paths that don’t lead where we had hoped. The key to a happier life is not to let regret bother you – you can’t change the past – but also to make decisions mindfully, perhaps thinking ahead many years.

When you’re 80 years old, what will you wish you had done differently?

Whatever that is — go do it.

Published or updated on June 5, 2014

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About David Weliver

David Weliver is the founding editor of Money Under 30. He's a cited authority on personal finance and the unique money issues we face during our first two decades as adults. He lives in Maine with his wife and two children.


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  1. Real Money says:

    This is a great article that applies to so many areas outside of personal finance! #3 is quite relevant to me right now; can’t stop meeting people! Thank you for this.

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