10 Habits That Help Me as a Manager

Many years ago I was interviewing for a management job at a growing tech company. After a long day of meeting with engineers and product managers, I made it to the final boss, the VP of Engineering. He introduced himself, put his hands together at the fingertips, and said, "Tell me your top accomplishments for the last three and six months."

I froze up. It had been a very busy year. I’d worked on a wide variety of things. I stalled. "Hmm... Let me think about that." He quickly cut me off. “No. That's not a good answer. You should be able to answer that without hesitation. Communicating the value you bring to the organization is an important part of being a leader. My advice for you is to set a calendar reminder. Every three months write down the top achievements for your team and your personal ones."

I was not offered that job. But I appreciated the great advice! After the interview, I set a calendar reminder, and every quarter since that day I have written down my top accomplishments. It's a very helpful habit for reasons I describe below. Many things that help me succeed in my role as an engineering leader are simple habits, like that one. I developed a set of daily, weekly, quarterly and annual routines that I'll share in this post. Many were tips given to me by coworkers, some I read about in blogs and books.

These habits are all personal actions I would practice regardless of the type of project or team I’m working with. This is definitely not a comprehensive list of everything managers need to do to be effective. They’re just a few things I find helpful. Here are my habits:

Daily Habits

Identify Your Top Six Priorities

I use a to-do list in Evernote to record all my pending tasks. During the day I’ll agree to do some work and add a task to the bottom of my to-do list. The list gets long during busy periods, so I prioritize it daily using the Ivy Lee Method. Productivity consultant Ivy Lee recommended this method to Charles Schwab in 1918 as a way to help his company’s executives be more efficient. It’s very simple. At the end of work each day you rank your top six priorities in order of importance. When you start the next day, work on the tasks in priority order. That’s it! I typically set out to tackle three-to-six tasks per day, so the Ivy Lee number seems appropriate.

Write and Share Daily Intentions

Most software engineering teams start each day with a “standup” meeting where each member summarizes what they plan to focus on that day. The team I currently work on is distributed across US and EU time zones, so we do this asynchronously by writing that info into a Slack channel used for daily standup posts. I find it helpful to record my daily intentions as it motivates me to complete what I publicly said I’d do. Having those entries written down also helps me remember what I accomplished when I write my weekly status update.

Keep an Emotional Journal 

Since the COVID-19 pandemic started I’ve been trying to keep closer tabs on my emotions. After experiencing strong feelings like stress, irritation, fear, anger, or excitement, I jot down a brief note about the emotion and situation in a notebook I keep on my desk. Recognizing and naming your feelings is an important part of building emotional intelligence. My daily entries are useful to reflect on when I write my weekly impact journal entry. They often describe the emotional roller coaster I experience while encountering setbacks, pitfalls, and small wins.

Weekly Habits

Update My Calendar

It’s important to start your week with a good plan. As a manager in a medium-sized company, I usually have 2 to 4 hours of meetings per day. Many of those are recurring like 1-on-1’s and weekly staff meetings. Others are ad-hoc project meetings that I need to prepare for in advance. I take a few minutes each Monday morning to look at the week ahead, canceling or declining meetings I don’t need to attend, and adding blocks of personal time for accomplishing the tasks on my “top six priorities” list. This helps me spend my time intentionally.

Exercise

Exercise is an important tool I use to manage stress. I’ve been going to the gym twice a week for years and doing the same simple workout. It’s such a regular habit that, after years of repetition, it requires no will power or deliberate effort on my part. It has been tricky adapting my exercise habits during the pandemic, but I’ve made do with jogging, YouTube yoga, and buying a bench and a few free weights for my basement. Whatever routine I follow must be so easy that I have no excuse not to do it. I also listen to things I enjoy while exercising like music, podcasts, and audiobooks as a rewarding motivator.

Review Indicator Metrics

In the seminal management book “High Output Management”, Andy Grove recommends establishing indicators to help you understand how you’re progressing towards your goals. Pursuing metrics blindly can cause unintended problems, so Grove recommends using “paired metrics” that show both the positive effects of your teams’ focus as well as the negative consequences. An example is pairing Jira velocity (quantity) with the bug rate (quality). I’ve managed infrastructure owning teams over the last few years, so I’ve tracked metrics like:

• new platform adoption %

• weekly production incidents

• off-hours paged while on-call

• security tasks open past due date

Every Friday morning I add a new column in my “indicator metrics” spreadsheet then record 10 metrics for the week. This process helps me model how work flows through the system, and allows me to see if the team made progress or was interrupted by reactive tasks. It also produces data I use to create charts showing trends like the percentage of customers migrated to the new platform over the last six months.

Write in an Impact Journal 

During an all-hands meeting, a VP at my company mentioned they keep a work journal where they wrote down the impact they made each week and how they felt about it. I started doing this and found it’s a very useful way to reflect. After starting his habit, you can scan the weekly wins you recorded every three months to remember the highlights from the quarter. Writing down your impact is doubly useful because you can immediately copy-paste it into your weekly status report. I’ve also found it interesting to read through my emotions from the last three and six months. When I read about my greatest worries and fears months after a stressful situation has been resolved, it reminds me of the powerful emotions we experience during challenges, and that every crisis is eventually resolved one way or another.

Share a Weekly Update

Information flow within your organization is critical and it helps to have a planned, consistent approach. This often looks like a weekly email, shared doc, or internal blog post shared with your manager and ideally with your stakeholders. There’s great advice on how to do these including Laura Hogan's “Week in Review Leadership Comms” and my colleague Jade Rubick’s “How to be an information flow superhero”. Currently, my process is writing a “reflection” on Friday mornings in Koan, an OKR tracking tool. It's visible to leaders in my org and I also share it with the team I manage. The format of the update is: things the team accomplished, things I got done, after-hours on-call support issues, priorities for next week, and concerns I’d like to raise. I write this after reviewing indicator metrics and writing my impact journal entry, so it’s mainly a copy-and-paste exercise. As we’re all remote workers during the pandemic, this habit is even more valuable. Your manager and stakeholders need to know where your team is focused, what’s holding you back, what's finished, and what you’re working on next.

Quarterly Habit

Record My Quarterly Accomplishments

Every three months I write down my top achievements under these categories: 

• Team accomplishments

• Communications (internal blog posts) 

• Process work

• Helping other managers

• Hiring

I scan through my impact journal entries from the last 12 weeks and copy-paste the most impressive items into the quarterly accomplishment list. When it comes time for my performance review, which happens every six months at my company, I simply combine the lists from the last two quarters then share with my manager. Nice and easy.

It's great having a record from each quarter going back for years of the things I've helped my team do and other things I've done personally. If anyone asks what I've done over the last year, I know where to look to help jog my memory. Sometimes I go back through the lists during times of doubt and uncertainty to help me remember what is possible. Reflecting on how you overcame past struggles can provide insight into your current challenge.

Annual Habit

Create Personal OKRs

Each year on January 1st, I open a Google doc and create a list of personal OKRs (objectives and key results) for the year. I usually have three or four top objectives with about five measurable results under each one. After writing my list of new year’s resolutions, I set a biweekly calendar reminder to revisit and update my progress. Christina Wodtke, author of the book Radical Focus on OKRs, has some great tips about using personal OKRs here. 

Personal OKRs help me focus on my health, family, friendships, and things I aspire to do outside my 8-to-5 job. Life is not all about work. It can be easy to continue thinking about work challenges on nights and weekends. This habit helps remind me there are other important things in my life.

Any Suggestions?

Have you formed a productivity habit you find particularly useful? Is one missing from my list? I’m curious about what works for you. Feel free to share your favorite habit in the comments below. Thanks!

My Advice for New Managers

The scariest change in my career so far has been my transition from software engineer to manager. I wasn’t sure if I was ready and didn’t really know what to expect. People in my organization were unsure if I'd be good at the new job. Many engineers I worked with at different companies considered management to be an unpleasant and undesirable task. Was this career change a good idea? There were so many unknowns.

Most new managers have similar feelings of fear and uncertainty. Our industry has been expanding for decades as software eats the world, and all that growth leads to hiring new engineering teams, which creates demand for new managers. Engineers that show an aptitude for leadership, project management, or communication will likely be asked the inevitable question: “Are you interested in being a manager?” If you said yes, or are considering becoming a manager in the future, this post contains my advice for you. Some of this advice was given to me directly, and some of it are things I wish someone had told me when I was starting as a new manager. 

Here’s my advice:

1. Don’t Freak Out

The day I was asked to become a manager, the CTO requested I meet him in the big conference room. It was eight years ago. I’d just returned from a sabbatical, which was a great perk the startup I worked for offered after five years. The timing for my sabbatical had been ideal. I’d just gotten married and completed grad school, and after the 5-week break, I was recharged and ready to take on new challenges. My grad program had been geared towards preparing software engineers for leadership positions, but I had assumed my move to management would happen 5 or 10 years down the road. When offered a management job, I said I wasn’t expecting it so soon, but I accepted.

I asked a few general questions about how to start. The CTO went through some logistics then said, “My main advice to you is: don’t freak out.” He was a direct communicator, which I appreciated. “Something will always be on fire at any given time. It’s normal. Don’t panic.” he added. This was the first management advice I’d received, so I pondered it over the next few days. Was everything always really going to be on fire?

In my experience, the answer to some degree is yes. There are always issues to deal with as a manager of varying urgency. Maybe your startup will go out of business if you don’t deliver new features customers will pay for soon. Maybe your SaaS app is experiencing massive usage growth, and the system is starting to melt down under the production load. Or maybe the new person you just hired is being rude and fighting with everyone. Previously, you may have been assigned a specific area to be responsible for and worry about. Now as a manager, you accumulate the concerns of everyone on your team, and it adds up.

Given that there are always urgent things to be concerned about, it’s important as a manager to consider the impact your reactions have on the team. People naturally want to consult the team leader when things aren’t going well. How will you react? In human group dynamics, teams look to their leader in a time of crisis, and it is pretty concerning when that leader is freaking out. It’s very unsettling. You in no way feel reassured that everything will be OK when that happens. 

Part of becoming a manager is adapting to this new reality. You’re exposed to more emergencies, more interpersonal conflicts, more problems. And that’s OK! Eventually, you get used to the fact that triaging (perceived) emergencies is part of the job. You’ll build more skills and self-confidence around handling “emergencies” with practice. Eventually when someone pulls you aside to say “This thing is on fire! What are we going to do?”, you won’t freak out. You’ll think to yourself, “Great, it’s time to do my job. I got this.” Your calm, confident reaction will be much appreciated.

2. Negotiate for a Trial Period

Many wise authors in the blogosphere have written that management is not a promotion, it is a total career restart. It’s a different job that requires a new set of skills. You may discover you don’t particularly enjoy the role. If you’re being honest with yourself, you may decide you aren’t as effective as a manager and want to return to an individual contributor (IC) role where you were previously making a big impact. That’s OK! Trying out a management position then deciding it isn’t your preferred career path is a common scenario.

You won’t really know if you’ll enjoy or excel at being a manager until you try it. My advice is to negotiate for a trial period. Ask the person offering you the management job if you can try being a manager for a set period of time, then have the option of returning to your previous role if either of you decides it isn’t a great match. Give yourself enough time to learn the basics, fail at some things, try other approaches, and repeat a few times. Six to twelve months should be a sufficient trial period. It will take longer to develop your skills as a manager more fully, but you should be able to assess whether you like the job in that time frame.

It’s easiest to make this type of arrangement at a company where you've already proven your chops and are trusted as an IC. Starting as a first-time manager at a new company makes it harder to set up this type of arrangement, but it’s still worth exploring. Ideally, you work for a company that supports people moving between management and IC roles as your career goals and the business’s needs evolve. Some of the best contributors were once managers, and they have empathy for the things managers need from their team to succeed. It’s often in a company’s best interest to normalize the transition back into and out of management roles, as it’s better to retain valuable employees than to lose them because they determined a career in management wasn’t the best fit.

3. Get Support

Being a manager will often be emotionally difficult. People will ask you for help with their toughest personal challenges. You’ll need to make difficult hiring and firing decisions that will have a major impact on people's lives. There will be a sense of pressure and high expectations coming from your company’s leadership. You’ll encounter new problems that weren’t your responsibility to fix before, like mediating conflict and addressing performance issues. On top of all this, you won't always be able to ask your teammates for help in the way you did when you were their peer, as it will now seem inappropriate in some situations.

Some new managers put on a brave face and try to handle everything on their own. This approach is not recommended and won’t set you up for success. You need to ask for help. Find a mentor that will be able to spend a few minutes with you every week or two, listen to your problems, and offer you advice. It can be another manager in your company or somewhere you worked before, or maybe another manager you met at a networking event. You may not be as comfortable sharing all your fears, concerns, and anxiety with your direct manager, so getting an additional person to confide in is helpful. Sometimes just hearing someone say, “Oh, that’s normal. I’ve been in that same situation several times” can be very reassuring.

One of the most useful support tools for managers at my current company is our “Mini-Manager Group”. Basically, new managers are placed into a group of random managers from different parts of the organization that meets every week or two to discuss challenges. It’s a great way to share tips and best practices, and I highly recommend setting up something similar if you’re at a medium or large-sized company. 

What if you’re at a smaller company and there are only one or two managers? You can join an online community like the Rands Leadership Slack. If you live in a metro area, there are probably leadership meetups like the PDX Engineering Managers meetup in my city. If you can’t find an experienced manager in your field, expand your search to anyone that has managed people.

4. Read Management Books

Learning lessons as a manager takes time. You'll try various approaches with different teams on numerous projects, and slowly learn what works for you. You will not be prepared on day one. To fast track your learning process it’s important to read some books about leadership and management. This may sound obvious, but it’s still important.

Reading advice from experienced managers helps prepare you for the many common situations you'll encounter when you're supporting and managing people. Some management tasks like facilitating a reorg or delivering performance reviews may only happen once or twice a year, so you won’t have frequent opportunities to learn by trial and error. It's much faster to learn by reading about the successes and epic mistakes of others.

Here are the five management books that I found the most helpful:

1. The Manager’s Path - This book describes the roles of technical leads, engineering managers, and higher levels of management. It’s a great primer for understanding the expectations and challenges of each role of the management career path. 

2. High Output Management - Andy Grove is a great writer and very persuasive. Written in the 80’s, some of the examples are a bit dated ("email will be huge!”), but much of the advice is timeless as human nature and the role of a manager remain fairly consistent over the decades. Groves describes how the performance of a manager should be evaluated and what successful management looks like in practice.

3. Radical Candor - Personally, I have a deep-rooted desire to make people happy and to shy away from conflict. That tendency can be problematic as a manager. Sometimes the most important thing we can do to help people is to give them uncomfortable, honest feedback. This book provides great strategies about how to have tough conversations with people to discuss the things that matter most.

4. The Five Dysfunctions of a Team - This book will resonate if you’ve been on a team that was struggling and the group dynamics became toxic. It helped me understand the behaviors and emotions I felt and observed when I’ve been on dysfunctional teams and projects. This book will help you recognize problematic behaviors and provides tips for reestablishing trust and team alignment. 

5. How to Win Friends and Influence People - Don’t let the clickbait title fool you. This is one of the first books I read after becoming a manager and it helped me start thinking more about my own emotional intelligence. As an introvert, I've felt "socially challenged” for much of my life. This book helped me see that some aspects of human nature are fairly universal and that social etiquette can be learned and improved just like any other skill.

If you want some shorter management advice in addition to books, here are some blogs to check out:

• Ask A Manager - Answers reader questions about management topics.

• Lara Hogan’s Blog - Management advice from Lara, formerly a VP of Engineering at Kickstarter and Engineering Director at Etsy

• Rand in Repose - The blog of Michael Lopp, author of “Managing Humans” and VP of Product Engineering at Slack

• The Year of the Looking Glass - Essays about management by Julie Zhou, a Product Design VP at Facebook.

Final Thoughts

If you’re considering the move to management, I hope I didn’t scare you off! Being a manager is a role I’ve found very fulfilling. It’s rewarding to help your direct reports develop their careers and to find ways to help teams thrive. Management isn’t an innate talent, it’s a job with skills that can be learned, and our industry definitely needs the help of people who are willing to give it a try.

If you’re an experienced manager, what’s your advice for people just getting started? Is there something you typically tell new managers, or a favorite management book you’d recommend? I’d love to hear your thoughts. Feel free to add some tips in the comments.

What I Learned at the Lumber Mill

The foreman called me up to the control room one morning. It was my second week working at the lumber mill and already I hated it. After marching up the grated metal staircase and into his office, I removed the earplugs we wore to protect against the mill’s loud machines. “Yes?” I asked curiously. He pointed down at my workstation through his office window. “What you’re doing down there… it isn’t making it.” I was a bit dumbfounded. “Not making it?” I asked. He nodded.

It sunk in that he was disappointed with my performance. “Am I going too slow?” I probed. “Yeah.” he responded emphatically, raising his eyebrows as if I’d asked a stupid question. “If you don’t pick it up down there, I don’t think you’re going to make it here.” That’s all he said. Not sure what to say, I let him know that I understood and marched back down to the plant work floor. But I didn’t really understand.

Before my junior year of college I needed to find a summer job. I spent the previous summers working outdoors in the carrot fields, but that comparatively pleasant job was no longer available. I looked around in Madras, my rural hometown in central Oregon, to see if I could find a tech job. I contacted a small tech company in the area which supported mainframe systems. After verifying I didn’t have any experience, they told me they didn’t need my help. With few options left, I signed up at the town’s lumber mill, as it paid a few dollars above minimum wage.

I soon discovered why the lumber mill paid more than other jobs in town. The work was damn hard. My job involved waiting at the bottom of a conveyor belt while a team of skilled saw operators on the floor above me cut wood slabs into long boards that were several inches thick. All day long, a never-ending pile of boards would lurch toward me. I would inspect them, judge the quality of each board, and place them into stacks according to their quality grade. These boards were heavy. At the end of my eight-hour shift my arms and back were very sore. Every night I’d eat a huge dinner and fall asleep early, exhausted.

The work was mind-numbing. To defend against boredom I’d play out elaborate fantasies in my imagination. Most of them involved performing at a school talent show which resulted in my becoming popular and well-liked, something I yearned for after struggling to fit in during my first two years of college. I also tried to devise an algorithm that would allow me to sort and organize the boards with minimal effort. The job could be much easier, I thought, if I could just figure out a better system. I put in just enough physical effort to keep up with the conveyor belt’s relentless supply of new lumber.

After my chat with the foreman, I felt ashamed. I was failing at this simple job that didn’t even require a high school degree. My shame quickly transitioned to anger. How dare he say I was inadequate at this stupid job? Determined to prove him wrong, I directed my anger into the work. No longer would I carefully inspect each board. Speed was now my goal as I yanked the boards off the line and threw them into roughly sorted stacks. I remember sweating heavily as my blood boiled. The work started to feel more like the conditioning workouts I’d done on the high school wrestling team. I went home that day fuming, more exhausted than ever, wondering how many days I could keep this up.

A funny thing happened over the next few days. Each day I’d come in fuming and slam the boards around, almost theatrically. My coworkers, noticing my exertion, started smiling at me. “You’re working hard down there!” they’d say. After an athletic performance over several days, I managed to keep well ahead of the boards stacking up at my workstation. I was often standing around, breathless, waiting on the senior coworkers above me to cut more boards for me to stack. I was no longer able to distract myself with mental fantasies. It was too hard to think about anything but the task at hand when I operated at full speed.

The dynamic in the break room started to shift. My coworkers started chatting with me more. Many of them were Hispanic and decades older than me. They called me “gringo” and shared stories about their weekends and families. They asked me about my situation, and I asked them about the delicious smelling home-cooked lunches they brought in to microwave. The group seemed to look up to a guy named Juan. He had a very serious demeanor but liked to tell deadpan jokes and tease people in a friendly way. I liked Juan.

Even my boss seemed to warm up to me, throwing me occasional looks of approval. He conducted weekly safety meetings by telling stories of his relatives and coworkers that experienced serious workplace accidents. His sister forgot to use a hair tie. Her long hair was caught in a gear, ripping part of her scalp. Like others in town, one of his fingers had been cut short at the joint, a visible reminder to be careful around mill machinery. He advised us to stay focused and pay attention.

As I worked hard to keep ahead at my station, I frequently stood around panting, waiting for more boards. My boss noticed and started giving me special assignments. One afternoon I was sent to another plant to clean up an outside area, a sunny reprieve from musty, sawdust-filled mill. Another day a nearby building had employees out sick, so they sent me over to help. A mom of one of my school friends worked there, and I kept thinking about all my classmates whose parents worked at the mill, and how hard it must’ve been to drive home and take care of their kids after a long shift. My favorite special assignment was helping an old timer inspect some giant trees that came in on a truck from Idaho. As I lifted huge 50-foot slabs for him to look under, he told me about the history of the lumber industry. He said trees like these were very rare because decades of logging had depleted the old forests.

Midway through the summer, Jacoby Ellsbury joined the team. He went to my high school and would later go on to play baseball for the Red Sox and Yankees. When we were both caught up at our stations, we’d be sent to cut boards together at a two-person saw table. Jacoby was fast with this hands and I had a great time trying to match his pace. Looking back, it was such a risky job for him. Sawing a few fingers off could have prematurely ended his career, costing him millions in major league earnings!

Near the end of the summer, I was in the best shape of my life and actually enjoyed the work. One day at lunch Juan asked me about my plans. I told him I had a few years of college left and was studying computers. “Don’t come back here. We don’t want to see you here anymore.” Juan said coldly. Taken aback, I looked at him. He had the serious expression of an adult trying to deliver important advice to a youth. He explained that working years at the lumber mill took a physical tole. His body was sore. The crew had to worry about getting injured and not being able to work and support their families. He wanted me to stay in school and get an office job. I smiled, nodded, and said “That’s the plan.” I thought about Juan when I was back at school, struggling with difficult classes.

Working at the lumber mill taught me that resenting a job and trying to do the bare minimum is not fun. It’s a lot more entertaining and fulfilling to challenge yourself and see just how much you can get done. Your coworkers appreciate your effort and determination. Your manager will take notice and start assigning you new, interesting challenges. I’ve seen this dynamic play out in several jobs, both as an individual contributor and as a manager. Often when I think my current job is stressful and hard, I remember back to lifting boards all summer. My white collar jobs have all been much easier in comparison.

Wait, I Pay How Much for Digital Services?

$366.83. Per month. Really? I added up the cost of every digital service my household subscribes to, and that’s the monthly total. It seems like a lot!

Why put my digital finances under the microscope? I wanted to gauge my digital spending to determine if I was comfortable with spending more. Recently I've felt motivated to pay for higher-quality news. The growing trend of media becoming smaller, bite-sized, and "snackable" is producing content of questionable quality. Reading a bunch of click-bait news is both easy and tempting, like eating junk food, while slogging through a full book is more like eating your vegetables. At least that's how I've heard it described.

Despite my enthusiasm for books, I don't always have time for focused reading. Sometimes I only have five or ten minutes, and I'd like using that time to keep up with what's happening in my industry, and the world at large. So I started paying for news from a few sources I trust to deliver insightful and interesting analysis. These purchases felt difficult to justify. I've been reading free news on the internet for two decades. Why start paying now?

Another trend affecting my spending is companies like Netflix and Spotify offering streaming services with monthly contracts attached. Individually these products seem cheap. I wondered, though, how much was I spending when I added them all up? How much more news, music, and streaming shows can I afford?

As a disclaimer, I want to acknowledge that I am very privileged to be able to afford these non-essential services. At best they're educational, but are often they're just frivolous entertainment. When I was in my twenties and on a shoestring budget, I remember agonizing over the decision to sign up for a $40-a-month cell phone contract. That represented a significant chunk of my monthly discretionary spending. These days a $4 coffee or $10 news subscription doesn't seem like a lot on its own, but they add up.

So, here's how my $366.83 breaks down, in pie chart form:

What’s included? Let’s go through what’s in each category, starting with the biggest slice of the pie.

Digital Access - $236.68 (64%)

Without internet connectivity, I can’t access any of these services, so I’m including them. Interestingly, these access charges dwarf all other costs, and add up to almost $3000 a year!

Verizon ($196.68) - I know, right? This cost may not be “fair”, as it’s a family plan covering voice and internet for three smartphones (myself, wife, and mother-in-law). That’s $65.56 per iPhone. Given how much time I spend using the internet on my iPhone, it’s arguably the most important.

Home Internet ($40) - I use Fibersphere, the internet service provider came with our apartment. They only offered me one speed option: 100 Mbps. Seems like a great deal for only $40!

Infotainment: News - $39.98 (11%)

I didn’t expect this to be the biggest “content” category. Apparently, I like news.

New York Times - Digital Subscription ($15) - The New York Times is my trusted source for global news. I appreciate their investigative journalism. Their basic digital plan gives me and my wife access to NYTimes.com and their apps.

Stratechery ($10) -  This is the first digital newsletter I’ve paid for. I discovered Ben Thompson’s work through his Exponent podcast, where he discusses strategy in the tech sector with co-host James Allworth. He previously worked for Apple and Microsoft, and delivers insightful analysis about the business models driving the industry. After I became hooked on his podcast and blog Stratechery, I wanted more, so I subscribed to his 4-times-a-week newsletter. It’s now one of my favorite news sources.

Nuzzel ($9.99) - Nuzzel is my favorite app, hands down. It helps me sift through all the noise on Twitter by surfacing the links that are “most shared” each day by people I follow. It’s a simple feature, one that Twitter should implement, and it’s incredibly useful. Their app is free, but I pay for “Nuzzel Pro”, which offers the ability to filter out news (e.g. “Trump”). The filter isn’t worth $10. I just want to give them money so they stay in business.  

Medium ($4.99) - I love reading and writing on Medium. It’s a beautiful product that enables anyone to publish news. This is another news source that is free, but I pay for membership anyway. I don’t find their member-only content worth $5, but I don’t want Medium to go out of business, because their free content is definitely worth more than $5.

Entertainment: Shows and Movies - $35.97 (10%)

Binge watching shows during rainy Portland winters is a therapeutic stress relief activity. It’s also a guilty pleasure preventing me from reading and writing more. Importantly, it’s cheap.

HBO Now ($14.99) - I typically sign up for certain shows like Westworld or Game of Thrones. That reminds me, GoT season 7 is over. I need to cancel this subscription!

Amazon Prime ($10.99) - Prime includes free 2-day shipping from Amazon bundled with a movie and show selection where I occasionally find something good to watch. Unusual combo, but I like it. Thanks, Bezos.

Netflix ($9.99) - Their content selection is pretty slim, but a few times a year they’ll have a binge-worthy show like Stranger Things or House of Cards. Also, nature documentaries. My cat enjoys those as much as we do.

I didn’t include movie rentals in this category. We typically rent one a week from Amazon for about $5, depending on how busy our weekend is.

"Productivity Services” - $24.22 (7%)

This category is a catch-all for a few cloud-based services I use.

Dropbox ($8.25) - I use Dropbox for our family’s laptop backup strategy. It keeps our files sync-ed and accessible via our laptops and their mobile app. It’s only $99 a year for 1TB of storage, which seems like a great deal. If our laptops are stolen or destroyed, our files are safe up in the cloud.

iCloud ($1.98) - My wife and I both have the $0.99 monthly iCloud plans, which buys us 50GB of storage each. That’s enough to store cloud backups for our phones, which is the reason we pay for it. This is also a great deal for the piece of mind knowing that I could drop my phone in a lake and my photos would be safe.

Squarespace ($10) - For professional purposes, I feel obligated to have a personal blog. I only write one or two posts per year, so I’m not sure it’s a great deal at this price. Squarespace is a great product, though. It’s very easy to use, and their WYSIWYG editor makes it super simple to customize my blog’s appearance.

Evernote ($3.99) - I use Evernote all day long at work to take notes. I like how it’s organized, and that it’s available on all my devices. This is another product I technically don’t need to pay for, but I do anyway out of appreciation. Their “Plus” plan does allow me to sync across all my devices (laptop, iPhone, iPad), while their free version only lets you sync two.

Infotainment: Books - $14.99 (4%)

Audible ($14.99) - I love listening to audiobooks during my commute, which is where I do most of my “reading”. Audible lets you download one new book a month. I typically listen to 10-12 per year, so this plan works out great. Their iPhone app is excellent and overall I’m very pleased. The value I receive from listening to books from anywhere is much greater than the $15 cost.

Entertainment: Music - $14.99 (4%)

Apple Music ($14.99) - Apple got me hooked with their 3-month free trial. I started discovering new music again after many years of listening to the same old songs. We have the family plan, so we can both listen to music in the car, gym, or on the bus anytime we want. I found interesting music for the gym on Apple’s curated workout playlists. Spotify’s service cost the same amount and I think they have better social sharing features, but I’m too lazy try it, as I’d need to re-create my playlists.

Final Thoughts

The biggest shocker after running the numbers was the price of mobile. I’m not mad, though. Smartphones are incredibly useful! I also realized that I’m paying $34 for services that I don’t need (HBO after watching GoT) or that don’t require payment to use (Evernote, Medium, Nuzzel). The final surprise for me was that, after access costs, I spend more on “News” than any other category. I would have guessed it’d be “TV and Movies”. Maybe that’s just my dated expectations, as I remember cable bills costing between $100 to $200, back before people cut the cord.

I’m glad I took the time to do this analysis. This list will help me determine where I can cut to save some money.

What do you think? Am I grossly overpaying for digital services? Are there any “must have” services you use that aren’t on my list? I’d love to hear about it! Feel free to criticize me or offer advice in the comments below.