29 Essential But Weird Tools You Wish You Knew About Last Year: The Ultimate Personal Productivity Stack

Justin Winter
11 min readJan 5, 2017

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Several friends have asked me several variations of the following over the years…

Justin, what software do you setup your employees with and use personally for email, calendar, web browser, etc.?

What do you recommend and use for your desk setup? Laptop? Keyboard? Mouse? Chair?

So instead of laying out an email response, I decided to just pull this together here so I can easily send this link in the future and hope that someone else finds some value in my learnings.

A philosophical note: I have experienced first hand, as well as been party to, the longterm negative effects of purchasing inexpensive options for most all of these items which are clearly not items to skimp on. This list is not meant to optimize to the least expensive stack, nor is it trying to be fancy because we have a lot of venture capital. The investment in these options is meant to strike a balance to optimize for ROI over a 12 month period when factoring in per employee productivity and output. All while at the same time actually increasing moral and making you and your team happier as you work.

Hardware

1. Smartphone

Would recommend an iPhone over Android. I am on the annual upgrade plan with Verizon. Yes, it is not the cheapest. Yes, there are better things to do with your time than optimize the crap out of your cell phone bill to save a couple dollars a month. Get the best tools and then move on.

2. Laptop

I purchased the newly launched MacBook Pro shortly after it was released this past year. I did the one with the fancy touch screen in it, it is not worth the money, so far at least. It is a novelty right now. I would go with the brand new 13' Macbook Pro with the basics specs unless you are a FT creative running adobe products all the time. Developers and designers own macs 9/10 times so they develop first, and sometimes only for Mac OS so the best apps come out, particularly for the worm and productivity genre, first.

If on a budget or buying for employees, I have had a ton of success buying Macbook Airs and Macbook Pros on craigslist for $600–1,000 depending on the model. If you have a little more time than cashflow right now, just work craigslist and save some money. Refurbished from Apple directly is also a good option as well.

3. External Monitor

You have to use an external monitor. Just running on that laptop all day will jack up your neck long term and increase fatigue during the day, limiting what you can get done. That being said, this is a ‘save’ not a ‘splurge’ item unless you are a full-time designer or creative professional. Go with the top selling 24" monitor on Amazon. This one from Acer appears to be at the top right now and looks like a solid choice.

4. Mouse

Here is the mouse that I have purchased for every employee I have ever had. Your hand is on this thing most of the day, don’t save a dollar here. It is worth the money.

5. Monitor Arm

Part of the setup is getting the monitors at the ideal ergonomic height to limit neck and back fatigue+maximize desk real estate to keep desk+sq. ft per employee costs low. So a dual-arm monitor, this is the one myself and the other 2 at my current company have. Everyone at my prior company, Diamond Candles, had all these as part of the standard package.

6. Laptop Tray

I discovered this handy little trick more recently. Here is the tray for your new MacBook. You attach this to the second monitor arm and adjust to match the height of your external monitor. Keeps the laptop up off of the desk which gives you more desk space.

7. External Keyboard

You will also need an external keyboard as well since your laptop is going to be up on that stand. The standard apple keyboard is good here. Refurbished is fine. If you are an accounting or finance professional and in a spreadsheet all day long, get the version with the number pad.

8. Miscellaneous

Outside of that, will just need to make sure you get the requisite cords. Currently, that will be a bit of a pain with the change on the new MacBook Pros to USB-C so you will have to get a couple of adapters.

9. Desk

Had these desks for everyone at Diamond Candles while I was there. Do not underestimate the standing desk. Don’t get a manual hand crank one, no one will ever use it. This little hack gets employees working longer because they can alternate from sitting easily (muahaha)! Make sure to just get the two button control+cable tray option.

10. Chair

For the chair, buy a used Herman Miller Aeron, Mira, or Sayl. Alternatively, if you look up an authorized dealer directory and call them up, they have a surprisingly low minimum order to get significant discounts on new ones. A new Aeron is easily $800, an order of 5 brought price down to half that per unit when I get a quote. The Sayl’s, which are the least expensive, but still quality, came down to near $300 a piece. These are also great used from Craigslist or even eBay. These things last forever and are super quality, so don’t be scared to go used. Will save $100–300 over a bulk buy per unit.

Software

All of these recommendations assume you are in the mac ecosystem. Some do have windows counterparts, however; will leave it to you to research that though. I have obsessively looked to optimize my workflow, constantly trying new apps and services, talking to others, top of the charts on Product Hunt etc.

This is what I have on my computer and we pre-install on computers that we give to our employees.

1. Browser

Chrome is the go-to. The extension ecosystem is the largest and lots of companies only write…well…extensions of their online services and software to Chrome, not Firefox or Safari, although admittedly those ecosystems are burgeoning.

2. Calendar, Desktop

Fantastical. This is one of my most used desktop mac applications. The key is to spend some time learning the keyboard shortcut, then it becomes second nature. I can schedule an event, either to block out a slot on my calendar to work on a project, or create an event and invite other people; all with the keyboard in a very natural way. Completely worth the one-time expense.

3. Calendar, Platform

Everything is running off of Google Apps so Google Calendar is the best way to go here. Both for my company(s) and my personal email for personal site. Microsoft has been getting their act together and is increasingly competitive but Google Apps is still the leader in integration proliferation, flexibility, and usability. If someone has been born and bread in the Microsoft Exchange ecosystem with Outlook, they will probably struggle with adapting to the ecosystem initially. In my experience, it is just a lack of proper on-boarding and training which leads to any bad roll outs.

4. Calendar, Scheduling

Calendly. Depending on your role at your company, you will likely need to schedule a lot of meetings with external parties. Whether you are in sales, business development, marketing, VP, C-Suite, or a founder, you are likely wasting a lot of time on back and forth emails. While there are a lot of great products that simulate a scheduling assistant, the work for the end party in my experience is actually more without a structured graphical user interface. I have my personal Calendly link in the footer of my personal and professional email signature and direct people to view my availabilities and pick a time that works best for them when appropriate.

5. Email, Desktop

I just ran Gmail in-browser for the past several years. A couple months ago I started testing all of the major mac apps that run email. By far, my best experience was with Newton. Very focused and minimal interface, supports keyboard shortcuts. Helps email get done and out of the way.

6. Email, Platform

Google Apps for the win. Gmail is the best. Next!

7. Internal Communication

Slack is being used by everyone for a reason. You should never really need to send an email to another employee at your company again, it should all be on Slack. You probably won’t get it until you use it.

8. Music

I typically have something on all the time if I am not on a call or in a meeting. Spotify is the best for a reason. Premium is a great value for all of the music that you will listen to in the background as you get stuff done.

Utilities

9. Bartender

Enter your Bartender. All of these apps begin to clutter up the user interface in the menu bar at the top of your computer. Found this simple utility that hides as many menu bar utilities as you want. With a simple selection, or keyboard shortcut, of the Bartender icon, all your apps and utilities are right there when you need them. More focus, less visual distraction, less cognitive load.

10. Clean

By default, I set the download location from my browser and application to the desktop of the computer. I never used to do this because it would quickly become cluttered and overwhelmed. This simple utility at a set interval, takes everything that has been saved to the desktop that day and moves it to a folder for that day. Still on the hard drive but out of your work space. You won’t be able to live without it even though you will forget that it is even there.

11. File Storage and Backup

I store all of my personal and family files in Dropbox. Although I have used Dropbox for a time with one of my businesses, Dropbox is definitely the better consumer option in my opinion. Loving my free 21 GB of storage from referrals back in the day when they came out with that program :-).

12. Evernote

This is where all my notes go. Brainstorming, business ideas, etc.

13. Messaging

Franz solved this huge hassle. So many messaging platforms. Facebook, Telegram, Groupme, Linkedin, Skype. One window to hold them all.

14. Flux

iOS just came out with the equivalent of this within the past year or so. Flux was the first real accessible utility for someone to moderate their blue light exposure from their personal computing devices so as not to interrupt their circadian rhythm, and thus their sleep quality and cycle.

15. Magnet

With all of these windows and apps, moving them around all the time can be tedious. This simple utility is an easy and intuitive way to snap things around and split a screen with a web browser windows or other app you have up at the time.

17. Task Manager

Wunderlist is used exclusively for personal use. Not for business. My wife and I have shared lists on here for things like grocery shopping, weekend to-do lists, and personal projects.

18. Password Manager

I historically used a password formula so that I could strike the balance between being able to remember a password and also having a unique password for every website where I had a user registration. The problem is that these approaches can be reverse engineered fairly easily and then re-applied so that someone tests logging into other things. Your next option is to use a completely random password, as in a random keystroke combination of letters, capital letters, numbers, and symbols. 9unHhfJF78*&$@972hbIHF for instance. But how to manage all of these random passwords? Enter a password manager. I have tried all the major ones for consumers. Most impressed with and satisfied with 1Password. Use this one. For business where you are frequently sharing passwords with other people, you would want a more robust solution that is truly a business first password manager.

19. Image Sharing

There is a good chance you currently communicate visually with other people in your own company or at other organizations. There are several simple file and screen-sharing tools out there, I have been most impressed with Droplr. This is one that all my employees have loved and used. It is often one the first thing they ask about if they ever have needed to switch computers because it is so engrained in their workflow.

I realize this list can probably be overwhelming. Bookmark it by hitting the little start here at the bottom so you can come back and reference it later. Download and try a couple and test them in your workflow over the next couple of days and practice.

This list certainly does not really hit on my personal list of mobile apps that I have found large value in nor is it an exhaustive list of business applications that I think any startup or small to mid-size company should take a look at. Simple a basic productivity stack for that can fit about 80% of everyone out there.

Questions, feedback, or clarifications? Highlight and annotate with comments and @ mention me, ex. Justin Winter, so I get a ping and hop in.

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Justin Winter

Husband of @ALynneWinter Co-founder/CEO @getboostopia Prev.@diamondcandles http://iamjustinwinter.com