Investing In Your Digital Life

When I was in middle school one of the “life skills” I was taught was how to balance a checkbook. By hand. As I grumbled and scratched out the arithmetic with my pencil I thought to myself – I’m never going to do this. And I was right. I never did balance a checkbook, and I likely never will.
I don’t store boxes of photos on archival paper, I mail few letters, I use a fax machine about twice a year, I don’t remember phone numbers or even email addresses, I spell poorly, I rarely add or subtract in my head. And it turns out that it’s ok – I don’t have to do any of these things.

All of this stuff that I am not doing, or storing, or remembering, doesn’t make me less smart or successful – it frees me to be more productive and do other things. Half of my brain is stored away in various computer programs. And that means I have twice as much brain to dedicate to things I find more interesting and fun.

The time that I am not spending adding up my transactions to balance my checkbook are instead spent clicking around graphs on that show how my spending and net worth are trending over time, giving me real, actionable information that is far more valuable than checkbook balancing would.

With that in mind, I thought I would share some steps to leveraging the resources that are out there that I find most helpful, along with some tips to help you get the other half of your house in order – your digital world.


Before we get to the fun stuff, it is important to make sure that your (increasingly important and confidential) online life is secure and protected. You will want to strengthen your first line of defense – your passwords. Then, you can easily set up a second line of defense (two factor authentication), where it is supported.

Before you start moving more of your life online, you will want to make sure that your information will be safe and protected. I recommend using a password service like LastPass, KeePass, or 1Password. These services will store all of your passwords for you securely, protected by one “master password” that you remember. Since you only have to remember one password, you can make it a very strong one. And then you can let the service generate strong, random, unique passwords for all of your other sites, which it will automatically fill in for you when you visit that site.

Two Factor Authentication
A number of sites support having a second input that is required to access their site when you are using a new computer or device. This means that if you try to access the service at a new computer you will have to type in a code from your cell phone – which means someone trying to get into your account would need both your phone and your password to do so.

Some of the sites I would recommend turning this on are: Gmail, Facebook, Twitter, Dropbox, and your password manager.


One of the best areas where going digital can improve your life is with your Finances. Now that you have strong, unique passwords for all of your banking sites (you did do that, right?), the next step is to start automating your financial life.

I’m a big fan of auto-pay, and I use it for all of my bills. Paying a credit card or other bill manually opens up the possibility of making a mistake, and those can be very expensive both in terms of fees and damage to your credit score. Beyond credit cards, it is worth setting up auto-pay for utility and other bills as well. It’ll save time, and once you are comfortable with it, you can even eliminate the paper statement. I have turned off paper statements for almost all of my bills, which significantly reduces the amount of paper clutter that I have to file away at home.

Credit Card
If you don’t have a credit card, you should. Paired with auto-pay and treated like a debit card, it is, simply, free money. This is first because it is a monthly, interest-free, one-month loan. A dollar today is worth more than a dollar tomorrow, and a credit card basically lets you spend a next-month-dollar today, every day. But, more significantly, most credit cards offer rewards. So, as long as you don’t carry a balance (you did set up that auto-pay, right?) or have a card that charges an annual fee, you pay nothing and just rake in the rewards.

I enjoy the simplicity of a flat-rate cash rewards card, and there are some good 2% cash back cards out there. I treat my credit card just like a debit card, never spending more than I have, and I have never paid a dime in fees or interest. I’ve earned hundreds of dollars in rewards and established good credit. It’s a win-win.
But wait, if everything is auto-paying and I’m not getting any statements in the mail, how will I keep track of my finances? The answer is, a free service owned by Intuit that will aggregate and summarize the information from all of your financial accounts. In addition to letting you see every transaction, the service will also provide useful summaries of your finances – with everything from spending, net worth, debt, etc available to see for any time period or over time.

The best thing about Mint, though it is not perfect, is that there is very little work needed beyond setting it up the first time. It can send you alerts for low balances, or when large transactions happen. It is intuitive and fun to use. I’ve used mint for five years and can’t recommend it highly enough.

Online Banking
If your only bank account is with a bank you can walk into (think Wells Fargo, BoA, etc.), then you may be missing out on some of the best Savings and CD rates. Online banks like Ally Bank consistently offer some of the best interest rates and serve well as a hub for your other financial accounts. With your physical-branch checking account linked to your online account, it is easy to move excess funds from your bank into your higher yield savings account.

It may even be worth considering a checking account with your online bank. Most online banks’ checking accounts will reimburse you for ATM fees (meaning you can use any ATM), and provide you with checks and envelopes to mail in deposits.


Here are some of the programs I find most useful for managing tasks, email, and storage:

Dropbox is a free cloud-storage service – which means that it is basically a hard drive on a server that you can access from any computer. You download the software onto your computer and it looks just like another folder that you can use – but everything is stored in the cloud, which means you can access it anywhere, and you can share it with other people. This makes it great for storing documents that you want to share or want to allow other people to edit too. It is super easy to use and offers decent security too (i.e. other people can’t see your stuff unless you want them to).


This free, simple, and attractive list making app can be installed on all of your devices, and it is sharable. This is great for grocery lists, since you will always have the most up-to-date list on your phone, and other members of your household can add or check off items from the list too. We use this for groceries, to-dos, places to go, other shopping, and more. I love that wherever I am I can quickly add something to any of our lists.

This free iPhone email app only works with Gmail (for now). The key feature of the app is that you can save an email for later – opting to have an email return to your inbox tomorrow, or this weekend, next month, or whenever you will be ready to process it. This can help clear out your inbox of all of those emails you aren’t ready to delete, but aren’t going to do anything with right now. The goal is to get everything out of your inbox, either by archiving it or saving it for later. It also has an intuitive gesture based interface and works well.

This program, which is free and works on all devices, converts articles on the web into pretty plain text and saves them for you to read. This is great firstly because it is a much more attractive and consistent reading experience than most web pages offer. It also means that you can read the article when you want, and on the device you want – it even has an option to send your articles to your kindle. With a browser plugin you can click one button and have an article saved to your readability reading list, and then read it when you get around to it. I have also found that the popular articles on readability tend to be really interesting as well.

Slickdeals is a web site that shares the best online deals. It sits on top of a huge and active forum of deal hunters and then the best deals float up to the front page, which updates throughout the day. It’s a great place to find the best deals on tech items especially, but all sorts of stuff shows up. One of the best things about this site vs. others is that it is a curated list – while there are tons of deals to be found in the forums by searching, only really good deals end up on the front page.

Amazon Automation
Amazon’s Subscribe and Save program lets you set up reoccurring shipments of various products from We use this for everything from cleaning supplies to food. It ships out in monthly installments from every 1-6months and you get a discount of 5% (15% if you have 5 or more items delivered in a given month). This can save the hassle of running to the store for the basics you need on a regular basis, and also helps me remember to replace things like water filters, toothbrushes, etc on regular intervals as they are delivered.

The Amazon Price Checker phone app lets you scan an item in a store and see Amazon’s price. Pretty cool!

I also use Amazon for most of my groceries since I live in a market served by Amazon Fresh. All of my basics are on a weekly auto-order and then I add the other groceries that we have on our grocery wonderlist. It is pretty magical to edit my grocery order at 10pm and have everything waiting outside my door at 6am the next morning. There may be another grocery delivery service you could try in your area.

(Full disclosure: I work for Amazon and this blog represents my thoughts and not those of my employer)


There are a few social sites that everyone should be a part of. You have surely heard of all of them – but maybe there is one you are holding out on because you aren’t sure if it’s for you.

Why do you need to be on facebook? Well, because everyone else is. (I’m looking at you, dad). Simply put, if you aren’t on Facebook, you are out of the loop. Your friends and family are on the site and sharing about their lives, they want you to be a part of their online community, and facebook is where that community mostly lives.

If you have a job, or plans to get one, you should be on LinkedIn. It is a great tool for keeping track of your network, and sharing your online resume. It’s not the sort of network that you visit every day (at least for me), but it is a valuable tool and everyone should have a profile.

First, lets address the main reason people don’t join Twitter – they don’t want to tweet. That’s fine. The reason most people should join twitter is not to post tweets, but rather to see the information others are sharing. If there’s something you are interested in, odds are there are experts posting interesting stuff on Twitter that you would enjoy seeing.

Haha, just kidding!


Thanks for taking the time to read through these tips! I hope that you find some of these helpful in automating your life to save time and money!

Are there other services that you would have included in this list?

One thought on “Investing In Your Digital Life

  1. Mom

    Nice blog Nathaniel. I like the idea of having more room in your brain to do creative endeavors instead of filling it with facts and figures. It's amazing you knew what the future would be in middle school!


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