How to Make Life-Changing Decisions

A few days ago, I went on a short trip back home to New York with our son. We flew out of BWI Airport and parked near where I used to work. It’s been about fifteen years since I was last in that area and it had changed significantly.

What was once just trees was now a shopping center. A few older buildings had been removed and replaced with commercial real estate, hotels, and gas stations. There was a lot more development.

It reminded me of my professional journey.

In 2008, I quit my job at Booz Allen Hamilton to work full-time on a blog.

I liked my job. It was very stable, and well-paying, the people were great, and the company was fair and supportive. I had a security clearance and job security. I could’ve worked there for decades and made a good life for myself and my family.

But I quit. It was a life-changing decision.

At the moment, it felt like a huge decision – quitting my stable job to pursue a “blog.” It was a hard decision and one that I spent quite some time on.

Here’s what helped me make this decision:

Table of Contents
  1. There Are Very Few Life-Changing Decisions
  2. There Are Very Few Irreversible Decisions
  3. Decisions are Rarely a Single Moment
  4. Not Acting is a Decision
  5. Set Your Fears
  6. Push Towards Something Good
  7. Talk to People You Trust
  8. Oh, You Won’t Feel Ready
  9. Finally, Minimize Regret
  10. Trust Intuition, Flip a Coin

There Are Very Few Life-Changing Decisions

For me, the first step is realizing that there are very few life-changing decisions.

We tend to elevate decisions above their true importance.

One of the biggest decisions you can make is your partner in life (or even have one). And we enter into these partnerships very easily. They’re potentially life-changing but we are quite cavalier about them. Divorce rates are high and the median number of sexual partners in a lifetime is 4.3 for women and 6.3 for men (CDC).

Another huge decision is where we work – yet the average worker has 11.9 jobs between 18 – 50. We enter into new jobs quite easily as well.

That’s because entering into a partnership, whether it’s a social one or for employment, isn’t life-changing on its own. You might be dating the one for you… or you might be dating the one right now.

If you accept that there are very few life-changing decisions, at least at the time you make them, then it becomes easier to make those decisions faster. It’s better to just make them than have them occupy your attention unnecessarily.

Also, couple them with the next idea and even big decisions become easier…

There Are Very Few Irreversible Decisions

When I quit my job, I didn’t burn any bridges. I told them that I was leaving to work on my projects. They were kind and supportive, as supportive as one is when you’re unlikely to see them again!

I would lose my security clearance and have to go through the clearance process again, but otherwise, I could’ve gone back. I might not have worked with the same company but I could’ve found work in the same industry.

Very few life choices are irreversible.

I can’t think of many decisions in my life that I couldn’t, in some way, go back and change.

If you get married and things don’t work out – people get divorced. If things aren’t working out and you divorce but later change your mind, you can get re-married.

There may be some cost associated – like if you buy a house and decide it’s not for you – but what is truly irreversible? Hardly anything.

I’ve always hated the idea that Hernán Cortés, upon arriving in the New World, burned his ships to show his men that there was no going back. They had to conquer the Aztecs or face death.

You have an out on every one of your decisions.

Decisions are Rarely a Single Moment

If you think back to the life-changing decisions you’ve already made, how many succeeded or failed based on a single moment? None.

You can point to the genesis of the change (quitting your job) but how you perceive the results (your life after quitting) depends on a lot of other decisions after that first one.

I look back on my decision to quit as a successful one because I grew the blog, sold it, and am still working on another one that, one day, I will sell. I’m still doing it and so quitting my job was a success.

But that’s only because the first blog did well. And that’s because of the decisions I made after I quit my job (and a healthy dose of fortune and good vibes).

You can influence the outcome, hopefully for the better, as you live your life after the decision.

If you don’t know which way to go on a decision, choose the one that is directionally accurate. Staying at my old job meant climbing the corporate ladder. I’d eventually move into project management, being involved in more proposals, then executing those proposals if we won, etc. It was not the life I wanted.

I chose entrepreneurship. It had more risk and income volatility. There was no “known path” forward. But it meant I was in charge and also responsible for it all and I was comfortable with that. It was in the right direction.

Not Acting is a Decision

“Every man has two lives, and the second starts when he realizes he has just one.” — Confucius

I think about that quote quite often. I find that people are separated into two camps – those who take an active role in their lives and those who take a passive role in their lives.

One, by definition, is not better than the other. Tragedy is when someone changes halfway through their life because they realize they’ve been living below their expectations.

Don’t let the magnitude of the decision stop you from taking action because that is itself a decision.

There was a phrase that we used at work (borrowed from the military) called OBE – overcome by events. It’s when events happen that make your decision or plan irrelevant or useless.

A good example might be buying a house – let’s say you are discussing buying a house with your partner. You come up with a plan, the financing, how you’ll repaint, what furniture you’ll get, … all these plans over a week. You go back to the realtor and say you want to put an offer on the house – except it’s already been sold.

While you were discussing and planning, the house was no longer available. That’s OBE.

I’d argue this is the worst possible result. You spent all this time crafting a perfect plan but due to your delay in acting, a decision was made for you.

You were not buying that house. Not by choice, but by force.

Not acting is a decision and often the worst one.

Set Your Fears

If you are paralyzed in analysis, consider “fear setting.”

This is a concept I learned from a TED talk given by Tim Ferriss in 2017.

I will let the video do the explaining, well worth the 13-minute watch:

For big decisions, this exercise is useful because it can help you identify the potential negatives of your decision and how you can mitigate them.

In quitting my job, I knew that if it all went badly, I could always go back to work. I wrote a simple resignation letter and didn’t burn any bridges. My skills were in demand, I had gotten a security clearance, and I was still young. If the blog flamed out, going back to work wouldn’t have been pleasant but it was always an option.

In doing this exercise, you may learn that the fears aren’t as serious as they seemed in your mind!

Push Towards Something Good

When it comes time to make the change, do it because you want to move towards something good and not because you want to move away from something bad.

Some folks who pursue FIRE (financial independence, early retirement) push hard because they want to leave a bad work situation. Maybe it’s a bad boss or work they hate or an organization that sucks. If they save enough money, they can quit.

While that can be motivating at the moment, it will hurt your chances of success after you make the change. Quitting a job you hate is easy but what are you working towards? What happens after you quit? That’s what will help give you a purpose once you are no longer working.

This is a struggle many retirees face. Some have a laundry list of things they wish to accomplish. That’s wonderful.

The act of quitting will be easy but trying to figure out what you’ll do next is hard – make sure you work on that while you are working towards making that decision. That’s the only way you will be able to see that decision as a success – if you have something to work towards on the other side of that decision.

The ones who are simply looking for an exit are in for a challenge. It’s like walking out of a prison and not having a ride. Find your ride before you leave.

Talk to People You Trust

Making a life-changing decision is always going to be hard. It’s even harder if you try to do it by yourself.

Your decisions will impact other people, so take the time to discuss the decision with them. I spoke with my lovely wife about quitting my job and she was supportive.

By supportive, I don’t mean that she was a cheerleader and would be there no matter what happened. (she was all that but that’s not what I mean)

I meant she pointed out all the times I’d talked about wanting to own and run my own business. She told me how excited I was to work on it and how I wasn’t that excited about work (and this was a workplace I enjoyed, I didn’t hate my job at all!).

She made a case to me about why quitting was the right choice and that I could always go back. She was another perspective and helped me make that decision.

When you talk to your closest friends and family, they will see things you don’t. They will see what you’re more excited about and what you despised.

And best of all, they can be there to pick you up if your decision goes south and celebrate if it exceeds all expectations.

Oh, You Won’t Feel Ready

With many life-changing decisions, it’ll never be perfect. You’ll never feel ready. There will always be a twinge of doubt and fear and anxiety.

But it’s important to set a date and work towards something, rather than have an ambiguous “time” you’ll make the choice.

Your date doesn’t have to be specific, especially for decisions with a lot of input. You may wish to have some preparatory milestones in place to adjust the timing of the “big” choice.

But having dates is like setting up a plan – it gives you something to work towards.

Eventually, you’ll feel ready. This may be the day of the choice or months afterward, but you’ll get there.

Finally, Minimize Regret

When thinking about decisions, I first assess the magnitude. What will I think about this decision in a year? Five years? Ten? Twenty?

Many of the decisions in our lives don’t last beyond the moment we make them. Many don’t last the day. Even fewer last a week.

What did you wear last Monday? What did you eat for lunch last Wednesday? What show did you watch on Thursday night? That’s not to say those decisions are not important at the moment, far from it.

The point is to spend an appropriate amount of time on it and then decide quickly. You won’t regret (at least for long) what you wear or eat today.

But for those life-changing decisions, spend an appropriate amount of time but do so with this key idea in mind – how do I minimize future regret?

I chose to quit my job to try blogging full-time because the blog was doing well and I wanted to spend more time on it. I felt I had a unique opportunity that I had to pursue. If it worked out, wonderful. If I took my shot and it didn’t work out, I could go back to work.

Which choice minimizes future regret? Quitting.

Trust Intuition, Flip a Coin

We were talking with a friend’s brother about whether he should quit his job and do something else. I remember telling him a little “trick” I had heard but never tried personally.

The trick is to flip a coin to help you decide. In the case of quitting a job, on heads, you quit. Tails, you stay.

As you flip, the one you’re hoping to get is the one you should do.

Or, go with what economist Steven Levitt, of Freakonomics fame, discovered – go for the change and abandon the status quo. It’s not a scientific study but I think it applies.

My intuition on this is that if you’ve thought a lot about a decision, you’re looking for a change. This is especially true if you consider it a life-changing one. I’m happily married, so I haven’t given a thought about divorce. I like what I do for work, so I’m not thinking about a career change. The thought of selling our home and moving hasn’t come up, even though we know it’ll happen one day.

If you’re thinking about it, it’s already taken root in your mind. Maybe a change is what you want.

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About Jim Wang

Jim Wang is a forty-something father of four who is a frequent contributor to Forbes and Vanguard's Blog. He has also been fortunate to have appeared in the New York Times, Baltimore Sun, Entrepreneur, and Marketplace Money.

Jim has a B.S. in Computer Science and Economics from Carnegie Mellon University, an M.S. in Information Technology - Software Engineering from Carnegie Mellon University, as well as a Masters in Business Administration from Johns Hopkins University. His approach to personal finance is that of an engineer, breaking down complex subjects into bite-sized easily understood concepts that you can use in your daily life.

One of his favorite tools (here's my treasure chest of tools,, everything I use) is Personal Capital, which enables him to manage his finances in just 15-minutes each month. They also offer financial planning, such as a Retirement Planning Tool that can tell you if you're on track to retire when you want. It's free.

He is also diversifying his investment portfolio by adding a little bit of real estate. But not rental homes, because he doesn't want a second job, it's diversified small investments in a few commercial properties and farms in Illinois, Louisiana, and California through AcreTrader.

Recently, he's invested in a few pieces of art on Masterworks too.

>> Read more articles by Jim

Opinions expressed here are the author's alone, not those of any bank or financial institution. This content has not been reviewed, approved or otherwise endorsed by any of these entities.

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