Admitting What Is Obvious

I’m a writer—what are you?

Midjourney/prompt: "man looking out over a giant chasm that needs to be crossed, vertigo, watercolor"

Ignoring what is obvious incurs a huge cost.

It requires you to go about your day numbing yourself to the reality of who you are and what you want—which is a waste of time for you and everyone around you.

By contrast, admitting what is obvious is freeing and motivating. But it’s terrifying to do it. Sometimes the most obvious truths about ourselves are hard to see because the consequences of those truths seem so dire. 

This happened to me recently. I admitted a truth that was probably obvious to everyone around me, but not to myself: I’m a writer. This sounds so obvious that it feels like it is a joke. I write a weekly column at a newsletter that I started—of course I’m a writer.

But this is one of those truths for me. And I’m glad I can admit it.

If there are obvious truths like this for you, you should find them, and admit them, too.

Why you can’t admit the obvious

The poet Robert Bly wrote that we all lug an invisible bag around with us everywhere we go. We’ve been filling it since childhood with the parts of ourselves that are true to us—to how we feel and what we want—but that aren’t acceptable to the people around us. 

It starts with our parents: “don’t make noise during dinner,” or “in this family, we play baseball.” It continues with our teachers: “you’d be good at math if you only applied yourself.” Finally, it starts to come from peers in high school: “that’s nerdy,” or “you’ll never have a career doing that.

Each of these interactions causes us to put parts of ourselves in the bag. And the things we put in the bag are the obvious truths that we can’t admit, and that we try to ignore.

Being a writer is one of the things I tried to put in my invisible bag. For a long time, admitting that I am a writer and that I want to be a writer felt like it would force me to shed my identity as a founder, eliminate the possibility of building a consequential company, and seriously cap my potential career earnings.

So, I pretended to be a founder who also liked to write. 

The first clue that I wanted to be a writer was that, after I sold my last business—a B2B software business—instead of going back into software, I started Every. 

Every is a startup, so it lets me call myself founder. But on the inside, it also secretly lets me do the thing that I really wanted to do but couldn’t admit to myself or anyone else: be a writer.

While I deeply enjoy almost every part of running a startup—coding, sales, marketing, managing, fundraising, etc.—writing is the thing that I’ve always loved the most. 

I knew this back in third grade when I wrote a 100-page novel in longhand on loose-leaf sheets of paper. But after writing that novel, I decided I needed more life experience to be a real writer, so I “retired.” 

In fifth grade I read a biography of Bill Gates and became enamored with entrepreneurship, so I decided to start a Microsoft competitor. I called it Megasoft. I learned to code so I could build an operating system to compete with Bill—and even though the operating system never saw the light of day, it set me off on a path building software businesses.

Both of these parts of myself have always been intertwined in a braid. But now, I’ve decided to shift the emphasis. I’m not a founder who also likes to write. I’m a writer who also likes to build businesses.

Living in this truth—the truth of what is obvious—is freeing. It will make me the best writer I can be. And, I think—paradoxically—it will help me build better businesses.

When you admit what is obvious, you start to improve

Billions of dollars in value are wasted every year by people doing the high-status thing they wish they felt compelled to do instead of the weird, low-status thing they actually want to do. Why is this value wasted?

You’re never going to be great at something you want to want. It’s always going to be a half-in, half-out kind of thing—instead of the all-in endeavor that greatness requires. Doing what you want to do, by contrast, lets you go all in.

As soon as I admitted to myself that I am a writer, it was easy for me to throw myself into it with wild abandon. Suddenly, I was sucking down great writing and furiously scribbling in my notebook. I made a list of skills I wanted to build and topics I wanted to cover. I realized how important it is for me to go deep on the future of AI and scientific discovery, AI’s power as a tool for creative expression, and its importance as a method for understanding ourselves. I recommitted to publishing this column every week. It felt like I didn’t have enough time in five lifetimes to do everything I wanted to do—and I feel like my writing is significantly better than it has ever been.

Who’s going to win in that scenario? Will it be me, or someone who wants to write but can’t seem to bring themselves to sit down at the keyboard?

Of course, doing this required me to grapple with a problem: how to square wanting to be a writer with wanting to build businesses. It was scary to want to be a writer because it meant giving up on being a founder. But as soon as I admitted the obvious, something else happened:

I started to find heroes who had done exactly that.

When you admit what is obvious, you can find examples to look up to

Once I admitted what was obvious, I realized there are a lot of people who have done something like what I want to do.

Bill Simmons is one such example. He built The Ringer, a sports and pop culture website and podcast network, which he sold to Spotify for $250 million. Simmons was both the CEO of The Ringer and one of its main stars—The Bill Simmons Show was the marquee podcast on the network. 

How’d he manage to square the circle between creative output and running the business? As far as I can tell, he stuck to what he’s good at: creating content, and spotting and developing talent. Then he recruited and maintained a core group of trusted operators around him who handled the rest of the business. He sets the vision, and they execute.

Once I found Bill Simmons I saw this dynamic at play in a thousand other places. Neuroscientist and philosopher Sam Harris mostly spends his time writing and recording podcasts, but he also founded Waking Up, a meditation app that helps his audience apply and practice the mindfulness skills he writes about. Sam doesn’t run the business day-to-day, though—he has a trusted general manager to handle that, so he can focus on thinking and creating. Other examples abound: Nate Silver, who started data journalism site FiveThirtyEight and is one of its main voices; Shane Parrish, who founded the popular blog Farnam Street; and Hank and John Green, the brothers, writers, and YouTubers who started both VidCon and creator merchandise company DFTBA; Gwyneth Paltrow who founded Goop.

I had previously been blind to this way of operating because it’s so anathema to the usual tech ethos, which is to hire other people to do the creative work, rather than continue to do it yourself.

But it makes a lot of sense for a creator-run business to be structured in this way. The best thing a founder of any business can do is focus on what they are uniquely suited for—and hire people better than them to do the rest. In a creator-run business, the founder should focus on making the product.

Once I found this way of operating, I started to bend my world that way. I made a few key hires (to be announced soon!) and began to hand off some of my day-to-day operational responsibilities. I’m still intimately involved in every aspect of the business, but my day is significantly more focused around doing the best creative work I can for Every—and I expect  that to pay significant dividends for the business over time. 

It’s truly the most satisfied, excited, and aligned I’ve ever felt running Every. Which brings me to my last point:

How could I have done this sooner?

How to admit what is obvious

Admitting the obvious is to take a scary leap. It is to make decisions that bring your life into alignment with what you truly want—rather than what you think you should want or what others want from you. It is to risk taking the low-status meandering path, instead of the high-status linear one. 

It can be easy, in retrospect, for me to wish I had done this earlier. To think that it might be possible to white-knuckle my way through future admissions of this kind, to give up all of my internalized shoulds, and any temptation to be affected by the desires and pressures of the people around me. To want to leap that gap in a single bound, and to believe that I could if I tried hard enough.

But I’m not sure that’s possible. Sometimes the obvious truth is hidden from you for a reason, and it takes great care and lots of time to see it. 

Spiders weave webs across gaps that cannot be crossed by crawling or jumping. Instead, when a tiny spider wants to weave a web across a large distance, it produces a fine adhesive thread that it allows to catch and drift along the wind. It can feel by the sensitive vibrations passed along the thread when it catches and adheres on the other side of the gap. Then, it carefully walks across that first strand like a tightrope walker, laying another thread down as it goes.

It weaves back and forth like this—carefully, one step at a time—until a web is formed out of thin air. 

I think this is the way to admit the obvious. Loose a single thread in the direction of what you want. When it catches—follow it, and strengthen it. Eventually, you’ll be ready to cross the gap with confidence and spin a web of your own.

Like this?
Become a subscriber.

Subscribe →

Or, learn more.

Read this next:

Chain of Thought

How Hard Should I Push Myself?

What the science of stress tells us about peak performance

2 Oct 17, 2023 by Dan Shipper

Chain of Thought

AI-assisted Decision-making

How to use ChatGPT to master the best of what other people have figured out

6 Oct 6, 2023 by Dan Shipper

Chain of Thought

Using ChatGPT Custom Instructions for Fun and Profit

How to 10x ChatGPT with personalized answers

17 Sep 15, 2023 by Dan Shipper

Napkin Math

Crypto’s Prophet Speaks

A16z’s Chris Dixon hasn’t abandoned the faith with his new book, 'Read Write Own'

13 Feb 1, 2024 by Evan Armstrong

Chain of Thought

Quick Hits: New AI Features From Arc and ChatGPT

The future arrived faster than I expected

2 🔒 Feb 2, 2024 by Dan Shipper

Thanks for rating this post—join the conversation by commenting below.


You need to login before you can comment.
Don't have an account? Sign up!
Denise Shipper 9 months ago

Beautiful! So proud of you! 💖

Dan Shipper 9 months ago

@deniseshipper thanks mom!!! ❤️❤️

George Levin 9 months ago

Man, this is well-written and very inspiring. It's exactly what many people, including myself, need. Thank you for sharing. As a founder, I place so many unnecessary labels on myself. Letting go of each one feels like I might not meet someone's expectations. Strangely, these expectations only exist in my mind, holding me back from being true to myself.

Even the label "founder" seems to dictate how I should behave. It's a freeing thought to let go of this baggage and labels and just do what feels right without overthinking how an activity might be labeled.

Dan Shipper 9 months ago

@george_7539 thank you for reading! glad it was inspring to you :)

appreciate you sharing your story. labels are interesting...i think sometimes they can be super helpful, but sometimes they function as boxes that keep us hemmed in. glad you're exploring letting go and seeing what happens!

Avishek Banerjee 9 months ago

I am a software engineer and uber love being just that! Took almost 5 years to accept that. Also took me down the taxing path of being a Manager and the scenic route of being a Product Manager, both of which I did reasonably well. But the joy of seeing the code come to life is simply unmatched by anything else!

Dan Shipper 9 months ago

@avishek_703 very glad you decided to go down the software engineer path with us ❤️

@sgray 9 months ago

Dan - we are twins. Two failed books by the agr of 21. On the second one the literary agent said “look, you’re 21, you wrote two whole books, you’re obviously a capable chap so go and find something you’re good at.”

I come from an entrepreneurial family and figured businesses are mostly story telling anyway so off I went.

28 years later I’ve founded many, invested in many, had a few good wins, but there is still an itch I haven’t scratched. My Bly bag is heaving with unwritten films and plays and novels.

Of course I’m too busy to do anything about it, I always make sure of that, but maybe soon a little window of time will present itself and I will gaze out of it wandering what’s next and recall this article and leap through.

Thanks for writing it.

Dan Shipper 9 months ago

@sgray thanks so much for writing this. i really hope you start unpacking your proverbial "Bly" bag soon :) maybe if you write something we can publish it on Every. best of luck!

@kensi.duszynski 9 months ago

Dan, I have not found a business newsletter that is as well-written, or that I enjoy more. I enjoy taking the time to read nearly every post that arrives in my inbox. This one, like so many others, met me precisely at the right time as I look toward 2024: What is it I love doing in business versus what am I tempted to build because I know it would be good for others, if not most desired by me? Thanks for sharing, well done to you, and congrats on this season of your work life and business.

Dan Shipper 9 months ago

@kensi.duszynski this means so much to me, thank you so much! we put a ton of time into the things we put out, and it's so great to know it's having an impact. i hope you find something you truly want to build—instead of something you want to want to build. good luck!

@albertocabasvidani 9 months ago

This resonates with me, too.

I'd love a practical example: how did you weave your thread across the gap?

Dan Shipper 9 months ago

@albertocabasvidani i think for me, starting a company that let me write was a really good first step. and, of course, before even that step i started a newsletter as i searched for what i wanted my next company to be.

so i'd say: what's the smallest possible step in the direction you want to go, that doesn't feel too threatening to your current identity?

Josh Todd 9 months ago

This is exactly what I needed to hear right now. Thanks so much, Dan, and keep writing!

@amitgupta147 9 months ago

Very clean. Gets the message across brilliantly. However, isn't it easier said then done. You made and sold a company and hence would have not had to worry about many other things(my assumption, I could be mis founded) , hence you could get your inner self to hear to your clarion call, fearlessly. But for many, you know exactly what I am alluding to.

Dan Shipper 9 months ago

@amitgupta147 this is a good point! i did indeed have a lot more opportunity to figure out what I wanted to do because of my previous company.

i will say, though, that the mental barriers were still quite significant. it took me many years to get over that fear and get out of my own way. but you're totally right that there are many people for whom real-world structural problems get in the way of following their passions. appreciate you sharing!

@rabbi 9 months ago

Wow! Clearly cuts right to the heart of the matter.

I wear a lot of hats (literally) in my roles in life and a long with all that those roles demand still fancy myself as retaining certain identities that distract me from my main job.

This article was a clarion call to self identify a solitary role, embrace it fully and use it to contextualize all the other areas of life that call my attention.

Dan Shipper 9 months ago

@rabbi glad you liked it! i think sometimes it's nice to simplify things by identifying and embracing a single role, and sometimes it's nice to allow yourself to enhabit many of them. it's a season of life thing—i'm enjoying being a writer right now. i'm hope it works for you too :)

Anna Krachey 9 months ago

This is a great post- I needed this call out today:) Would love to some female founders included in the examples- I know they're pretty specific, but surely there's one out there

Dan Shipper 9 months ago

@annakrachey thanks i really appreciate it! good callout, i had that same feeling when writing it and i should have included. i think gwyneth paltrow is an interesting one!

@plautsergioh 9 months ago

Great reading Dan! Good timing as well, when you see yourself about to make a big decision in what’s going to be the next adventure

Dan Shipper 9 months ago

@plautsergioh thank you!! really glad you liked it

@cpculp 9 months ago

philosophy … from philos and logos … the love of wisdom. you are a philosopher

@ba2458 8 months ago

Wonderful post, Dan!

Tiffany Lee Brown 8 months ago

This is all lovely, in its way... but it seems to assume that most people's big problem is daring to leave their high-status lives and careers — presumably attained as white males with middle-class+ upbringings and education. I chose the mostly "low-status meandering path" decades ago, despite having many privileges and advantages (white woman with a high-status education, middle class upbringing, etc.).

It's wonderful that you get to write professionally and be a money guy playing with startups, but sheeesh, it would go a long way if you would acknowledge the enormous privilege you bring to that position. Most of us will never have the resources, connections, influence, or knowledge to be a Sam Harris or Gwyneth Paltrow.

Several of my clients in creativity/writing/performance and in my Tarot and astrology practice are high-status professionals seeking to delve into creativity and a stronger relationship to nature and creativity. Working with them is a delight, and I deeply respect their search for meaning, their desire to be more of what they truly are.

Most, however, are to middle- and low-status meanderers like myself. They are artists, activists, Zen priests. They are writers, poets, travelers, caregivers to elderly parents, community members who cook vats of soup after the hurricane and make sure the neighborhood gets fed. Many are moms.

Many of them struggle to get by, balancing some kind of gig work or day job with their own creative and community outputs, and with the needs of their immediate and extended families. Some, like me, wrestle with partial or full disabilities, some of us with no government assistance for that.

The luxury of declaring yourself a writer is lovely. I did it in my teens and have been a professional, mostly freelance writer ever since. Congratulations on making that decision. However, I encourage you to recognize that there is an element of luxury, of privilege, at play. If you want to inspire others, consider becoming acquainted with the range of conditions others face, and acknowledge your own privilege when you write for a wide, public audience. To do less is... I don't know. Presumptuous? Out of touch? Gatsbyesque? It doesn't feel right.

Steve Kamb 8 months ago

Thanks for writing this Dan.

I started a site about helping nerds get fit back in 2009, and grew it by doing the only thing I knew how to do: write. After a few years it accidentally became a big team, we had app developers and growth and I was managing (poorly) a big team. After a 6-year detour of NOT doing the obvious thing, I finally fired myself to give me the space to get back to doing the damn thing that brings me to life, and got me here in the first place: write! Cheers man.

David Roseberry 5 months ago

found this post a few months after it first appeared. Thanks for it. But now, the obvious question: how do you find it. The thing you are, by nature, gifted to be.

Every smart person you know is reading this newsletter

Get one actionable essay a day on AI, tech, and personal development


Already a subscriber? Login