Facing the Paradox of Choice in Your Career

🚀 You may feel overwhelmed by potential career paths - Issue #181

The Paradox of Choice is a controversial phenomenon that suggests that an abundance of options isn’t necessarily a good thing. The more choices you have, the more you feel paralyzed by indecision. 

Numerous research findings confirm this human reaction across a variety of scenarios. Show people three options, and they will easily be able to pick one. Show them 20 options, and now they feel overwhelmed with the burden of comparison.

Also, people will often experience regret and dissatisfaction with their final choice. With so many options, shouldn’t the one that they selected be perfect?

In this TED talk, psychologist Barry Schwartz mentions a study that looked at participation in retirement plans. They examined data from Vanguard that they collected from about a million employees over 2,000 companies.

They discovered that for every ten additional mutual funds an employer offered, the rate of voluntary participation went down 2%.

“You offer 50 funds — 10 percent fewer employees participate than if you only offer five. Why? Because with 50 funds to choose from, it’s so damn hard to decide which fund to choose, that you’ll just put it off until tomorrow. And then tomorrow, and tomorrow, and tomorrow, and of course tomorrow never comes.”

You may think that this only occurs on a discrete decision-making level. Which box of cereal should I buy today? Not an easy decision when faced with an entire aisle with hundreds of choices in the average supermarket.

Which health insurance plan is best for my family? From personal experience, I know how complicated and painful this decision is.

However, the paradox of choice also occurs on a much larger scale with entirely different paths that you can take in your life. 

For example, given who you are, your education, and your work experience, you might think that the decision of career path A vs. B shouldn’t be an overwhelming one. Every step you’ve taken in life has funneled you deeper and deeper into a specific ladder to climb, hasn’t it?

But, the reality is that this is far from the truth. Options increase the longer that you live, the more you learn, the more skills you acquire, and the more aware you become of how big the world of opportunity is.

Why does this happen?

When I work with clients on defining their next career move, people tend to fall into two different camps:

  1. “I have no idea about what I want next for my career. I feel like I don’t have any good options.”

  2. “I have too many options for my next move. They all have good and bad points, and I’m overwhelmed with how to make a choice.”

I often find that this happens when people have decades of career experience. They have learned so much, done so much, and accomplished so much that they could do almost anything well.

They don’t face a lack of options at all. They have too many potential paths that they could take, with no way to predict their future satisfaction with a specific choice.

In some ways, this ties back to my previous article on “creativity” as a sculpting vs. painting approach. When you are just starting in your career, it faces you like a blank canvas.

You have no real experience yet, and now you have the task of placing that first dab of paint. Just get started. If it’s a mistake, it’s easy to scrape it off and start again.

However, when you’re in the middle of your career (or later), you’ve amassed a large block of focused knowledge, skills, and experiences. Add your natural talent to the mix, and now you’re faced with a somewhat overwhelming mass of potential that could be shaped in any number of ways.

This makes you feel like a sculptor. Where do you strike, and what do you remove first to change your career path? Make a mistake now, and it may be irreversible. This brings the distinct problem of loss aversion into play, as well.

You may want to move into path B with your career, but how can you give up the 15 years of experience that you’ve developed on path A? The pain of this decision is real, and I hear about it almost every week.

Even when someone is ready, willing, and able to accept the risk of giving up their first career, choosing their 2nd act career is far from easy. They don’t want to repeat the mistakes they made before. 

The decision causes even more stress because they have a burning desire for greater fulfillment and happiness. It has to be perfect.

First, be thankful

I know that it is stressful to face these choices. I’ve dramatically changed my career a few times over the past ten years. But, take a moment to realize why it is happening.

You are experiencing this precisely because you are smart, talented, experienced, and good at what you do. That’s why you have so many options.

Good things brought you to this point. I know that it does not feel very good right now, but some people never have much of a choice. Due to a variety of circumstances, some people were never able to ask the question, “What should I do with my life?”

Be thankful for your natural talent and the opportunities you’ve been given. Realize that you are in this situation because you do have potential.

You do have choices. You do get to decide what happens next in your life.

This is still an area of growth for me, as well. Practicing gratitude helps keep things in perspective

We tend to focus on the pain or friction in our lives, as we strive to make changes that will increase our happiness. In doing so, we lose sight of all of the good in our lives.

Reframe the stress of this moment as an opportunity. Rather than being overwhelmed, you are excited. Being able to make this choice is a rare gift that many will never have.

Next, determine what is most critical

Facing multiple choices is even more overwhelming if they have numerous complex attributes.

I deal with this every year as I compare different health insurance plans for my family. Dozens and dozens of variables lined up in apples to oranges comparison scenarios.

Retail stores also love it when they can overwhelm your rational decision-making ability with highly-salient attributes, which often mean nothing. Oooh, look at the diamond-matrix-pentile mega-pixel quantum-dots in that infinity edge screen!

Trying to make a complex decision like that is like trying to boil the ocean. Don’t let yourself get sucked into that game with your career options.

That’s why I ask my clients to create a list of the key attributes that are most important to them. Rank and weight them objectively.

Take the complexity that is overwhelming you, and break it down into a small handful of attributes that you can compare as quantitatively as possible.

For example, if freedom is your number one attribute, quantitatively score and rank your job options based on the freedom they will enable in your lifestyle. However, if total comp is your most important attribute, then rank your choices accordingly.

I want to take a moment to remind you how important it is to examine this list of attributes with fresh eyes. We tend to get into a habit of comparing our options in the same ways that we always have, or in ways that others encourage us to think.

For example, people do tend to consider total comp as the most critical factor when comparing job offers. But, the reality is that other factors will have a more significant impact on job satisfaction and happiness in the end. 

For example, one study found that adding 20 minutes of commuting for work every day has the same negative effect on job satisfaction as receiving a 19% pay cut. Ouch.

Then, set your sights on the horizon

When faced with a decision about the next step for your life or career, it is easy to become fixated on the next few months. If you’re a natural planner, you may be thinking a year or two out.

But, this isn’t very helpful for planning a lifetime journey. With short-term thinking, all steps feel like a similar move forward. It’s hard to compare and contrast them.

Taking a moment to define your long-term goals will help. 

  • Where do you really want to be in 10, 15, or even 20 years? 

  • How do you want to be making a living when you are that age? 

  • What do you want your life to be like at that time?

I went through a similar exercise a few years ago. I had spent about 20 years in Silicon Valley working in Tech. Most of my career planning was thinking a few years out, trying to chart the next obvious move to continue moving up the ladder.

When I became a VP at Yahoo, the options began narrowing. There weren’t many great VP of Product jobs within a reasonable commuting distance.

Luckily, I slowed my pace down and took a gap vacation when I left Yahoo. It gave me some time to clear my head of the old corporate perspective and the Silicon Valley rat race. 

I thought about what I really wanted for my eventual career lifestyle. I also thought about where I wanted my family to live.

I began mapping out paths between my long-term goals and the options available to me. It became clear that doing more of the same wasn’t going to take me to my desired destination anytime soon. 

It wasn’t easy to visualize a path to get there in my conventional career either, using typical planning forward. So, I tried something different, as I describe in the next section.

Finally, engage in reverse planning

Research has found that planning in reverse is often more effective than traditional planning for complex goals. Deciding what you want to do for the rest of your life definitely qualifies as “complex.” Once you have established your long-term life and career goals, start planning backward from that moment in time.

What needs to be in place for that future scenario to be true? Evaluate each of the options you are considering with that in mind.

Which one is more likely to take you to that long-term destination? Which one seems really attractive right now, but the cold hard truth is that you can’t picture how that path would ever take you to the destination you have in mind?

I’ve personally faced this a few times during my life and career. One path would look exciting, but I had to admit that there was a 5% probability that it would succeed to the point of delivering me to my desired long-term destination.

The other path wasn’t nearly as exciting, but I had to admit that there was an 80% probability of it giving me what I knew I really wanted in the end. 

Guess which path I ended up taking?

Choose what will take you where you really want to be

I left Silicon Valley. I’m currently writing this from my new home in the Sierra Nevada mountains surrounded by a forest, about an hour from Lake Tahoe.

I sold my BMW, and I now drive an old Toyota pickup. I gave up on the 5% path and embraced the 80% path.

I’m living where I want to live. I no longer have a commute at all.

I spend my days investing in my own business instead of working for someone else. I work with fantastic clients who are terrific people, instead of fighting with Machiavellians in a corporate office. 

I figured out what was most important to me, and gave up chasing things that I had been conditioned to believe were necessary.

It’s fun and exciting to play the lottery and dream about winning big until you finally realize that 90% of startups fail. It’s not nearly as exciting to go to work every day, manage your expenses, and slowly but surely save enough money for more reasonable goals.

My path is just that: my path. It’s not necessarily your path.

I would never presume that I could tell you what decision you should make for your own life. That’s not the point of this article.

But, if you’re at a crossroads with your career and feeling overwhelmed, I hope you now see that you’re not alone. Many talented people feel precisely the same way when they face this paradox of choice.

However, as I explained, there is a way to make it through to the other side and not regret the choice you end up making. It does require breaking free of expectations, identifying your real long-term goals, and some counterintuitive planning. 

Do this well, and you’ll be much happier with your decision in the end.


Larry Cornett is a leadership coach and business advisor who also hosts:

  • free Slack community for ambitious professionals who want to be more successful in their careers. However, if you’re not a knowledge worker or comfortable with tech, it’s probably not for you.

  • A mastermind community for solopreneurs and entrepreneurs who want more accountability and support. If you’re not interested in starting your own business someday (or accelerating an existing one), this community isn’t for you.

  • free community for independent creators who want to make a living doing more of what they love. Note, this community is for creative individuals who actually bring things to life (e.g., art, design, music, movies, photography, writing, pottery, etc.). Sorry, managers and agents, it’s not for you.

Larry lives in Northern California near Lake Tahoe with his wife and children, and a gigantic Great Dane. He does his best to share advice that can help others take full control of their work and life. He’s also on Twitter @cornett.