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12 Ways to Automate Habits So You Can Invest More and Improve Your Career

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Jam Choices

Customers shopping at an upscale grocery store encountered a tasting booth that displayed either a small (6) or a large (24) selection of different types of jam.

Of the roughly 250 customers who passed the bigger display, 60% stopped at the booth to try a sample. In contrast, only 40% of customers stopped to taste the jam at booth that had fewer choices.

So which booth sold more? The answer might surprise you.

You might imagine that the consumers who encountered 24 different types of jams would sample more flavors (they didn’t) and be able to find a flavor so perfectly suited for their palate they couldn’t help but take a jar home with them.

However – you’d be wrong.

Despite less customers stopping to sample the flavors, the booth with a limited selection of jams sold nearly 8 times more preserves than the booth with the greater number of choices (31 jars compared to 4 jars purchased). [1]

What does this mean for you?

The Paradox of Choice

Well, it means if you are planning to sell jam at the farmer’s market next year, you better not give people too many flavors to choose from.

It also tells a of potential problem you face when encountering too many choices in other areas of your life. That problem is – like the customers who faced too many flavors of jam – when given too many choices… you don’t make a choice at all.

Not making certain choices in life can have dramatic repercussions.

Take the example Barry Schwartz’s gives in his popular TED Talk about the paradox of choice. In his talk, he describes how people left money on the table because they were overwhelmed by the number of ways they could receive that free money.

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Schwartz’s cited a study that showed that the more retirement fund choices employers offer, the fewer employees participated. The ratio was: 10 more funds lead to 2% fewer employees investing.

That means if employers offer 50 investment options, 10% fewer people will take advantage of the (up to) $5,000 a year in free money from employers that would happily match their contribution.

“One effect [of choice], paradoxically, is that it produces paralysis, rather than liberation. With so many options to choose from, people find it very difficult to choose at all.” – Barry Schwartz

This insight can be a tough pill to swallow as an American. My culture would say there are never too many choices. But in reality, “the good plan you do follow is better than the perfect plan you don’t.” And too many choices paralyze us because it makes determining that “best” choice overly difficult.

So how do you start following some “good” plans?


Habits solve the paradox of choice because they allow you to fall into routines that limit your choices.

For example, there are 1,000’s of different workout regimens you can use to maintain your health. That is why people who are not in the habit of exercising find it so difficult to start.

On the other hand, if you are in the habit of going for a jog every morning, you don’t have to think about those 1,000’s of other choices every time you lace up for your morning cardio.

Morning Run

Because the right habits can shape your life is such a substantial way, when I started writing this post, it was going to be about how to create new habits.

It would start by showing you how to determine the best cues to initiating your habit. You’d then learn how to create a routine. That routine, through incremental gains, would give you whatever sort of longterm payoff you were looking to get (better health, more money, more free time).

For those who are still interested in that original article idea, I’d highly recommend reading The Power of Habit as well as our friend James Clear’s posts on habit formation.

However, I started thinking about why we set out to make new habits or set New Year Resolutions.

It’s likely because we feel as if there is something in our personal or work lives where we can improve. But let’s be honest – creating successful habits that are sustainable over time is really hard work.

What if we could get that payoff or improvement without all of that hard work? What if we could outsource our habits?

Fortunately, we can!

So instead of learning how to do the hard work of habit formation, I’m going to give you my personal cheat sheet to automating your habits.

Free Habits!

I found that there are 2 major areas in my life where outsourcing habits pays the biggest returns. The areas are: personal finances and work.

Let’s start with your money.


Financial Automation

Setting up a budget, saving and investing were all vital habits that used to be necessary to form if you want to create a comfortable future.

The reason why is simple arithmetic.

The habit of frequent managment of your personal finances leads to successful results because compound interest is exponentially more generous to those who save and invest over long periods of time.

That long term saving and investing used to be work.

Budgeting, saving and investing were all things that people had to take the time and energy every month to:

  • invest money in the stock market by calling your broker
  • transfer another sum into a savings account by going to the bank
  • balancing your checkbook
  • manually review your bills and spending to make sure you are living within your means

Not so much any more.

Here are the tools I have used to bring my time spent budgeting, investing and saving to nearly zero:

Budget will track all of your expenses so you’ll only have to wait for your weekly personal financial statement that automatically comes into your inbox:

Mint Budget

They also have a free notification service that instantly tells you whenever any fees hit your accounts so you can fix or at least not repeat the situation.


Acorns is an app you can download on your smartphone that will allow you to start investing small amounts of money into low fee index funds. is an online tool that allows you to automatically invest money into low fee index funds.


Invisible Hand is a browser extension that automatically searches for the lowest price on whatever you are buying online.

Automated Banking. Most banks allow you to automatically transfer funds to your savings or other accounts. I have automated my savings for my Health Savings Account that allows me to save money on my taxes each year.


Image Source:

Relaxing at work

Work Automation

Whenever I can autopilot anything with my work, I go for it. Lately I have been experimenting with more software to do this.

For example, one habit I was terrible about was keeping my files organized on my hard drive. Now, I have a program called Hazel do all of the work for me. If automagically sorting your files sounds like a good plan to you we’ve written about Hazel before here and here.

Other great habit outsourcing software tools include:

Keyboard Maestro





Another way for making sure you are in the habit of following all the right steps for completing certain work related tasks are checklists.

Checklists avoid blindspots. And before you think you are too smart for checklists and that they are only good for burger flipping teenagers, I’d like to remind you that ALL pilots are required to use checklists upon takeoff and landing. The medical community is also embracing the the power of the checklist to save lives.

Checklists make big screw ups less likely. So next time you perform a vital job function. Take a moment to write down all the steps you took. That way next time you won’t have to remember every step from scratch and you will likely avoid overlooking some important pieces to the procedure.

Lessons Learned

Habits are are hard. Systems and technology are easy. Don’t do work for work’s sake. If you can outsource or automate a habit, do it.

That way you can get all of the incremental gains of building more habits without all of the hard work.

Source Cited:
1. When Choice is Demotivating: Can One Desire Too Much
of a Good Thing?, a Columbia and Stanford University publication


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Posted by nicole  | November 17, 2014 at 9:48AM | Reply

>Despite less customers

Fewer. Fewer customers.

Posted by Christopher Williamson  | November 5, 2014 at 2:49AM | Reply

PocketSmith is better than mint and the company is wise enough to realise that the U.S. is only a small part of a large planet. :)

YNAB is too much of a time sink.

Posted by Simon  | October 25, 2014 at 11:31AM | Reply

Great idea, tech + systems can only be a good thing.

@Jay – Check out YNAB (You Need A Budget), works all over the world. Life-changing budgeting software for desktop/iPhone/Android.

Not strictly automated as you have to enter your details (although you can schedule transactions), but does an excellent job of making sure you live within your means with its four revolutionary rules; there’s a good explanatory video on the main site:

Posted by Jay  | October 19, 2014 at 4:43AM | Reply

Great stuff! However this is mostly for US (the finance bit), is there similar things for people outside US that you would recommend?

Posted by Noah @The Non-Accountant  | October 16, 2014 at 3:04AM | Reply

Great article, I love the budget automation habit. Will be having a look at Mint.

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