Essays
Drink the Radioactive Gatorade
My best description of the current moment is that a small subset of the population just realized they can drink radioactive Gatorade and get superpowers.
October 7, 2025The Awkward Adolescence of Ambition
Ambition is not willpower, hunger, or hustle. It is awareness, a noticing of something inside us longing to be heard and expressed.
May 29, 2025This is the Work
There's no shortage of stories about who you should be. Some are handed to you with love, others not so much. A few you carve for yourself.
April 4, 2025Exceptional People are Wonderful and I'd Like to Have More of Them
Are exceptional people rare flukes we're lucky to stumble across, or are there a lot more of them out there, just waiting for a bit of sun?
February 6, 2025The Compound Interest of Books
There's an unexpected upside to my bad habit of buying too many books: when they all sit unread together, they create a kind of natural selection.
August 27, 2024If You Want People to Remember, Tell a Story
In my work as an executive coach, I too often see leaders get frustrated when their team fails to understand a core value. A good story changes that.
February 13, 2024Get Beyond Treating Symptoms: Identify Root Causes
As an executive coach, I help people get unstuck. After three years and 1,400+ hours with clients, I wanted to share a bit about how I do that.
September 21, 2023Writing Beyond a Niche
Season One of Hoo Boy was the Season of the Hedgehog. Season Two will be the Season of the Fox. A fox knows many things, but a hedgehog knows one.
March 26, 2023Running Great One-on-Ones
1:1 meetings, when done well, are to a great working relationship as diet and exercise are to long-term health. A comprehensive guide to effective one-on-ones.
March 12, 2023Why We're Unprepared for Co-Founder Relationships
What makes business partnerships so much more likely to overwhelm us when compared to life partnerships? Start conditions differ, blame is easier than responsibility.
February 26, 2023Conducting a Time Audit
Dee Hock believed great managers should allocate 50% of time managing themselves. To manage yourself effectively, begin by examining how you spend your time.
February 5, 2023Avoiding the Startup Graveyard
Two problematic ingredients, low pricing combined with high-touch sales processes, create conditions that can seduce and ultimately destroy founders and their companies.
January 22, 2023Why Every Startup Hires the Wrong Sales Leader First
The Sales Learning Curve from Mark Leslie and Charles Holloway's 2006 HBR paper is essential reading for startup founders planning sales organization growth.
January 8, 2023The Should Factory
Your inner jerk telling you what you should have done. Should is a word we use to shame ourselves and others. Don't should yourself.
December 18, 2022Startup States: Jungle, Dirt Road, Highway
Based on Jeff Bussgang's framework, Andy Sparks explores three distinct phases of startup maturity: the jungle, dirt roads, and the highway.
December 4, 20221800's Wisdom: Three Components of a Business
Andrew Ure argued factories needed three harmonious systems: the moral system, the mechanical system, and the commercial system. This still holds today.
November 13, 2022The Roots of Your Obsession
What do you find so interesting that it out-competes Netflix for your attention? Every obsession has a legacy, and we can choose to embrace it.
October 30, 2022If Someone Quits, Who Will Replace Them?
Exceptional managers cultivate relationships with talented professionals well before job openings materialize. This is the art of bench building.
October 23, 2022The Story Behind My Latest Project, Hoo Boy.
The star of this issue is my latest project: Hoo Boy. It's a newsletter I send every other week where I write for founders navigating how to manage
October 16, 2022The False Cultural Promises of a CEO
Managers often operate in what the author calls the land of broken promises, claiming high concern for both people and production while delivering neither.
October 2, 2022We Don't Have a Word for a Great Business Culture
Using the Blake-Mouton Managerial Grid to explore why we don't have a word for 9,9 management, and why that's a disappointing commentary on our collective failure.
September 18, 2022Great Managers Manage Themselves First
Dee Hock, Visa's founder, challenged conventional management wisdom by advocating that managers should dedicate approximately half their time to self-management.
September 4, 2022A Model for Cutting Down on Gossip and Drama at Work
Andy Sparks explores the Drama Triangle, a psychological framework developed by Dr. Stephen Karpman in 1972 that explains how interpersonal conflicts emerge.
August 21, 2022The Stories in Our Heads (Fact vs. Meaning)
Andy Sparks explores how we construct narratives around observed events, distinguishing between facts and the meanings we assign to them.
August 7, 2022Does Your Calendar Reflect Your Priorities?
Years ago, Keith Rabois shared a principle that stuck with Sparks: your calendar should reflect your priorities. Most founder frustrations stem from misaligned time.
July 24, 2022On New Chapters (and My New Chapter)
Andy Sparks announces the launch of Hoo Boy, a new newsletter focused on business building and workplace culture, and explores Frederic Hudson's Cycle of Renewal.
May 31, 2022Captain's Log: May, 2022
My last letter was in October of 2021. Since then, I've written and re-written this letter at least three times. Maybe I should just send the damn
October 27, 2021Captain's Log: October 2021
You might be confused. Doesn't this email usually come from MailChimp? Yes, yes, it does. But I was sick of paying $50 / mo. for something I can
September 9, 2021Captain's Log: September 2021
A lot has happened since I sent Edition 7 of letters in April. Most importantly, I'm excited to share about my new climate-focused coaching company
September 8, 2021How My Coaching Works
The field of coaching has a ton of variability. So when I meet someone interested in working together, they inevitably have a lot of questions.
April 14, 2021Captain's Log: April 2021
Last week, we announced that paperback and hardcover copies of my book, The Holloway Guide to Raising Venture Capital, are available on Amazon.
December 28, 2020Captain's Log: December 2020
Each of us needs our own village of people, and 2020 has made that particularly hard. Even before COVID, I would often cite a quote from Kurt Vonnegut.
December 21, 2020Using a DSLR as a Webcam for Zoom Calls
My camera setup, desk accessories, and tips for using a Sony Alpha a6400 DSLR as a webcam for Zoom calls.
October 20, 2020Captain's Log: October 2020; Letting the Longing Do the Work
Six weeks ago, I wrapped up my last week as CEO of Holloway to pursue a vague new career made up of a mixture of research, writing, and coaching.
September 3, 2020The Next Chapter of My Career
This week, I handed Holloway's CEO reins over to my co-founder, Josh Levy. As we built Holloway over the last four years, I got the chance to explore the depths
- December 22, 2019
Failure is a Process
A few weeks ago, a Good Work reader asked if I'd write about recovering from failure. I was grateful to have been given the opportunity to think about this one.
- December 15, 2019
Knocking on Doors
Over the last year, I've spent a lot of time thinking about how we get the word out about Holloway. I've read more than I ever thought I would about marketing.
- December 8, 2019
Hilarious Mistakes
I loved video games in middle school. So when the Xbox came out, I made an appeal to my parents to purchase this glorious machine.
- November 24, 2019
Keepers
Work, as we often think about it, is a place to get things done, to put food on the table, to make that bread. But for me, work has also been the place I've met my closest friends.
- November 17, 2019
Applying Science Terminology to Business
At Mattermark, the company I helped start before Holloway, we were in the business of collecting data on private companies so investors could
- November 10, 2019
Benchmark Your Knowledge With the Urban Scale
Have you ever noticed that learning to swim feels a lot like drowning? At least at first. How can we tell when all that flailing around is actually
- October 20, 2019
Procrastination is a Useful Signal
Yoda said, 'Do or do not,' but do I did not. This week's Good Work is one week late and about procrastination.
- October 6, 2019
Polishing Hinges
In my century-old house, the hinges on every door are covered in layers of paint. For a hundred years, the people painting this house refused to find a screwdriver
- September 29, 2019
The Three Tenets of Trust
Trust is made up of three things: sincerity, reliability, and competence. And trust crumbles at anything less than having all three.
- September 21, 2019
Complaints Are Gifts
In the first few years I was managing people it felt like everyone had something to complain about. The grievances poured into a sad swimming pool
- September 7, 2019
Work Worth Doing
When work is a choice, why the hell do some people choose to do it? Why would someone with $2M, $50M, or $800M in the bank choose to do the kinds of daily tasks
- June 15, 2019
Reading Fiction Will Help Your Career
It's hard to make the case that studying someone who mastered a craft by reading their biography would be a waste of time.
- June 8, 2019
Books: The Perfect Career Companions
When I was nineteen, a friend and I started brewing beer. I headed to Barnes & Noble and asked the gentleman at the counter if there were any books
- June 1, 2019
Putting People in Play
Julian Weisser introduced me to a phrase I fell in love with this week: 'putting people in play.'
- May 25, 2019
You Exist Outside of Work
There's this perverted idea that taking time to rest is an indulgence, like catching our breath over the weekend is the equivalent of eating a swimming pool
- May 4, 2019
It's Your Ship to Steer
There's this Jim Beam commercial I love. It's called Bold Choices. It's the best commercial I've ever seen.
- April 13, 2019
Why You Should Take Notes on Everything
In Where Good Ideas Come From, Steven Johnson writes about what he calls 'the slow hunch.' Charles Darwin didn't wake up one day with the entire theory of natural
- March 30, 2019
Creating a Filter for Friendships and Collaborators
A few weeks back, a friend of mine asked me a question over text. 'Now that you are where you are in your career, fairly established, how do you
- March 24, 2019
Coaches Should Accelerate Your Growth
How coaches help founders develop a growth mindset and accelerate personal development through deliberate practice and feedback.
- March 9, 2019
Renovate Your Inner Self Through Journaling
Journaling is my favorite tool for self-discovery. Journaling has helped me realize I need to get out of a toxic relationship and recognize the negative impact
- March 2, 2019
A Non-Dystopian View of Work
A hopeful vision for the future of work that centers meaning, purpose, and human connection over productivity and optimization.
- February 24, 2019
Looking Within
Answers to what we're optimizing for can be troublesome. They're often not even the real answers.
- February 16, 2019
Ten Year Careers
My favorite people are irrationally passionate. They're the ones who get to work getting things done and forego the temptation to stick to talk.
- January 2, 2019
On Confidence
I doubt myself a lot. Everyone is totally just winging it, all the time is one of my favorite articles ever. It makes me feel far less alone with my fears.
- September 20, 2016
Failure, Depression, and Yoda
Isaac Asimov wrote a book called The End of Eternity. It's a great science fiction novel about a world where time travel is constantly used to change history.
- July 15, 2015
What Does a Startup COO Actually Do?
I believe the job of a founding COO is to do the most important things the company hasn't hired for yet, hire or delegate to someone in your place, and move on.