My friends who know me well know I have this concept I call work-work balance. And in sharing it with someone new, it’s usually met with a light chuckle. I never mean it as a joke. But nevertheless, people take it as my attempt to be snarky and witty.
I believe most of you, my readers, are familiar with work-life balance. A lifestyle that balances work and your life outside of work, often one that spends the capital earned though work. When I hear most people say it aloud, its most frequent use case is in avoidance of doing more work. But the underlying principle is that most people don’t enjoy the work they do. Rather, they find their joy and fulfillment in pursuing hobbies and passions outside of the confines of a 9-to-5.
Just like having a work-life balance is a privilege, having a work-work balance is, in my humble opinion, even more so one. Speaking of privilege, earlier this week, I had the fortune of hearing a rather profound line:
“If you do one thing in life that fuels and motivates you, then you should yourself lucky.”
So, in even talking about work-work balance, I admit I came from a position of privilege, but one I do not think is unattainable for those who also have the privilege of debating the technicalities of work-life balance.
Work-work balance is the balance of doing what you love doing with work that you need to do to continue doing what you love doing. To me, work that I enjoy doing — interesting projects — fulfills me. It gives me meaning and purpose in life. To best illustrate this concept, I’m going to have to steal Elizabeth Gilbert‘s line in a 2016 interview with On Being. It’s not the first, and it won’t be the last time I quote her here:
“Everything that is interesting is 90 percent boring.”
When you’re proud to have work be your identity
Starting something — anything that is going to be core to your identity, even if it is only briefly — is going to be unhealthy.
Being a great venture-backed founder is unhealthy. Starting a venture fund from scratch is unhealthy. Being a world-class content creator is unhealthy. Being a diligent and serial author is… well, you get it. Hell, even binge-watching the latest and greatest Netflix show is unhealthy.
It is also the difference between passion and obsession. One keeps you daydreaming; the other keeps you from sleeping.
I’m not advocating that everyone live an unhealthy lifestyle, but that the concept of work-life balance is a lifestyle that doesn’t fit everyone, but those who have not or have yet to find deep fulfillment in the professional aspect of their life. For those who have found their life’s work, work-work balance may be a more sought-after lifestyle. In working mainly with founders and emerging fund managers, their life stories seem to corroborate the previous sentence.
In the world of startups, I often tell founders, and have many a time, advised founders not to take venture capital. There is no shame in creating an great and fulfilling lifestyle business. But as soon as you take venture, that’s a different story. After all, another name for venture capital is impatient capital. It is the perfect permutation of not just ambition, but also of expectation. The greater you raise in venture, the greater the expectation.
A $10 million valuation is not a number indicative of your company value. In fact, I think the 409a valuation does a better job of that than what VCs price your company at. Rather, a $10 million valuation on a social media company is a bet that you have a 0.0025% chance — a 1 in 40,000 chance — that you’ll be as big as Meta. At least at the time of writing this blogpost. Equally so, a $1 billion valuation is a bet on the odds that you have a 1 in 400 chance to grow as big as Meta. As Uncle Ben said, “with great power comes great responsibility.”
And as such, the expectation and the will of your new bosses — your investors — is that you can scale a team that can help you capture that opportunity. And for VCs, or die trying. Many, if not most, great VCs would much rather you bat for the home run than walk a base. After all, the success of an investor is not defined by their batting average but the magnitude of home runs she or he hits. But I digress.
As a founder, you must love your work so much that it’s contagious. That it affects your investors, your team, and your customers. Why? Because in the course of building a rocket ship, there are a million and one things that can go wrong, and a million and two things that feel tedious, repetitive, and slow. And the work you enjoy doing must be so powerful that just the thought of being able to do more of it invigorates you through the long troughs between wins.
I say all this to every founder I’ve met who didn’t fall madly in love with their problem space and who expect venture funding. The going will get tough, and I, like many other investors, want to know that you have the grit to make it through this long, windy journey. Having a good pulse on work-work balance is one of a few proxies for that grit.
Of course, I do want to posit that a work-work balance doesn’t mean you should make prolonged sacrifices to your mental health, your sleep schedule, or your time with friends and family.
#unfiltered is a series where I share my raw thoughts and unfiltered commentary about anything and everything. It’s not designed to go down smoothly like the best cup of cappuccino you’ve ever had (although here‘s where I found mine), more like the lonely coffee bean still struggling to find its identity (which also may one day find its way into a more thesis-driven blogpost). Who knows? The possibilities are endless.
Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!
Any views expressed on this blog are mine and mine alone. They are not a representation of values held by On Deck, DECODE, or any other entity I am or have been associated with. They are for informational and entertainment purposes only. None of this is legal, investment, business, or tax advice. Please do your own diligence before investing in startups and consult your own adviser before making any investments.
In writing this blog, one of the greatest illusions I seemingly end up creating is that I know a lot. At least that’s what a handful of readers and friends have told me over the years. Truth is I don’t. And more often than not, I am learning and/or refining my thoughts as I am writing.
I’m gonna be honest. The script for this essay was going to be entirely different. In fact, I had exactly six hundred and eleven words written on another introduction to this piece. But in the past few weeks, I hit another seemingly insurmountable roadblock. Catalyzed by a conversation with a mentor who said: “David, you’ve confused movement with progress.” And she was right. The more I thought about it, the clearer it became. Snowballing upon itself until I realized how far I’ve gone when I mistook a compliment for an insult.
The more I read my previous intro, the more it sounded like total BS. Something someone would write never having experienced true self-doubt. I was my own harshest critic.
The irony of it all was that as I was interviewing other incredible individuals for the purpose of this blogpost, I felt I needed their advice below more than anyone else. In a way, I’m glad that some friends needed more time to collect and share their thoughts. In sum, this piece took me two months to put together. And every day, every minute, and every second was worth it.
As I’m writing this piece, I’m somehow reminded of a line Elizabeth Gilbert, author of Eat Pray Love, said in a 2016 interview with On Being, “Creative living is choosing the path of curiosity over the path of fear.”
The process
In concepting this essay, I spent more time than I’d like to admit beating myself up to get to the “right” phrasing of the question. And each time I thought I got closer to the “right” question, a day later, I would find myself second-guessing if people might even bother responding to a “lazy” question. A low-hanging fruit, so to speak. And the fallacy with a low-hanging fruit is that they’ve most likely been asked the same by others. Probably to the point of fatigue, paired with an eye roll. But the thing is… with the topic of self-doubt, it’s not a topic most people are comfortable sharing, much less in public. And equally so, are rarely asked a question on this topic. The flip side of the coin is that they too are less likely to answer such a question. In the end, I settled with a question I came up with two weeks prior.
Speaking on self-doubt, 25% of the people I reached out to in my existing network didn’t have time to respond. Another 20% refused within 24 hours. And another 20% agreed initially, but ended up refusing some time after the initial exchange.
In reaching out, I used a similar framework as I shared in my cold email template.
TL;DR: I’m writing a blogpost on self-doubt, and you were one of the first people I thought of in having been candid enough to share your life journey. What are some of the personal narratives, questions, or comments you find yourself regressing to when you’re filled with self-doubt?
The longer version: Recently, after sharing my own internal conflict (here and here), I had a number of friends and readers reach out to share their own struggles. With almost half of them mentioning at one point in time that “I wish I were like [insert role model’s name] because s/he seems to have it all down.”
But people, like you, are just as human and as real as the next person over. So, in my effort to use my humble platform to humanize the world around us, I thought you’d be one of the best to answer this question!
What are some of the personal narratives, questions, or comments you find yourself regressing to when you’re filled with self-doubt?
Because I also plan to share your answer in the form of a blog post, similar to a study I did last year, where I asked [names redacted] and some other great folks! By default, I will abstract your name from what you share. In this case, I will cite you as “[title]”. That said, if you’re open to me using your real name or would like a different “title”, please do let me know. If you’re curious as to why my default is not to include your name, this is why.
And I know your candor will help many more, like me, who are going, have gone, and will go through difficult times. So, thank you. I have nothing short of my deepest gratitude for not only your candor, your time, but also your willingness to share your thoughts with the amazing people in this world.
Warmest, David
My only ask
My only ask is that you stay open-minded as you read the below memoirs. For context, this has been the blogpost that I’ve gotten the greatest percentage and number of “No’s” from. In the forms of:
“This is not something I’m ready to share at this point in my life.”
“I’ve been too busy. Sorry.”
“I’m sorry. I don’t think I’ll have time to get to this.”
“I don’t think now is a good time for me to be involved unfortunately.”
It isn’t easy to share what each of my amazing friends have shared below. Some of which stories may never see the light of day without their courage. And I hope you let their authentic voice shine as much as, if not with more respect that you have given me all this time. On behalf of everyone here, thank you. Thank you for giving all of us the platform to share our most vulnerable selves.
Unless otherwise specified with their first and last name, the below names, listed in alphabetical order, are pseudonyms to respect the courage it took each and every one of them to share what they did: Andrei, Annie, Elijah, Harry, Liam, Lucas, Mateo, Mya, Stephanie, Zack
The question
What are some of the personal narratives, questions, or comments you find yourself regressing to when you’re filled with self-doubt?
“I have a rather conversational style of writing. I suspect it’s the product of some natural proclivities and the sheer joy that comes from clacking a keyboard.
“We live in a world where every action has the potential to be a performance. Performances, by their very nature, are meant to be judged—are they memorable? Funny? Heart-wrenching? All of us, whether we like it or not, are constantly on stage and constantly judged. Personally, I get stage fright, and don’t recall being consulted before I signed up for this part.
“My own vintage of self-doubt stems from being judged poorly by someone I need something from. I’m in a position of vulnerability, they’re in a position of power. An old turn of phrase from the Bible, later memorialized forever in A Knight’s Tale, captures what my psyche so desperately tries to avoid: “You have been weighed, you have been measured, and you have been found wanting.” The external “they think I’m lacking” becomes the internal “I’m not good enough,” and by then I’m well stuck in the swamp of self-doubt.
“For me it’s the idea of being rejected, rather than rejection itself, that causes self-doubt to metastasize. As the CEO of a venture-backed startup, this is not ideal.
“Two months back I had a bad panic attack. Wave after wave of self-doubt assailed me for hours after the attack subsided. Just yesterday, I had the minor upwellings of another one. Both were caused by pitches I knew I bombed (ironically, both investors ended up investing). In a perfect world, one in which I am preternaturally confident, the opinion of others shouldn’t stir feelings of self-doubt. In the real world, I care very much what others think of me.
“It’s easy to build stories in our mind to validate self-doubt, especially in the early days of a company when you don’t have a ton of evidence to beat back the self-doubt. I’m still not sure what the evolutionary advantage is to this pattern, to play devil’s advocate against ourselves, but it’s real nonetheless. We all do it. And the cleverer the mind, the more insidious the arguments.
“When this happens, my mind runs to something my dad used to say: ‘What you think about me is none of my business.‘ If I ever get a tattoo, it will be these 10 words. There’s something comforting, almost even glib, that enables me to turn the corner more quickly than I normally would. It’s a well-trodden path that leads me back to positivity, outcome independence, and abundance mentality.
“Self-doubt is inevitable. So rather than trying to avoid it, focus on leaving it behind.”
Of course, I couldn’t help but include Taylor’s afterword as well.
“Unintentionally mirrored after one of my favorite writers, John Gierach. John muses on life’s richest veins and uses fly fishing as his vessel.”
A blessing in disguise
“Self-doubt may feel painful at first sight… but in essence it’s a real blessing… because it helps balance one’s ego + falling for believing in their own shit! If you are trying to learn new things and explore uncharted territories… it’s inevitable to have self doubt. It’s almost like having a sense of danger when you are venturing in extreme sports let’s say.”
– Andrei, Managing Director at a VC Firm with 10+ Funds
Lily pads
“When I start feeling self-doubt, my mind immediately regresses to ‘lily pads’ or landing places of past memories where I feel like I could have done something better. I start to overthink everything I wish I could have done differently in past roles or interactions, and get paralyzed with fear that I will have the same regrets in the future based on the next choices I make and actions I take.
“Here’s a few questions I regress to:
How did I trick someone into believing I was the right person for this job?
Will I ever be able to match the level of success I had with a previous project or was that the ultimate cap of my success?
Do other people perceive a mistake I made in the past with the same level of intensity? Are they as fixated on it or was it something that barely registered for them?
“The things that have helped:
I think through the advice I would give a friend, and then I try to be as gentle with myself (which is a hard thing to do).
I remember that the best wins in life come from taking risks, and assure myself that if I don’t feel some doubt, then I am not pushing myself to grow.
I keep a folder of compliments and nice feedback I have received, and I go back and read through a few threads to remind myself I have been able to get through things successfully in the past.”
– Annie, Head of PR
I followed up with Annie after, if she could shed some more color on what advice she gives to herself, as well as an example of a compliment she finds herself revisiting when she finds herself wrestling with self-doubt. And here’s what she shared:
On self-advice,
“Look at your success over weeks or months, rather than by the hour. A single day may not feel like you’ve achieved everything you set out to do or landed a milestone, but if you can Zoom out, you are doing it right.”
On compliments,
“In response to a tough email I once sent, an executive privately emailed me to compliment my professionalism and how I had organized my thoughts. That compliment resonated because I had put hours of thought into that response even though it was only a few paragraphs long, and it meant a lot to me to have someone validate my thought process and my output. When I am doubting myself and worried my instincts are off, I go back to that email. I also try to put it into action and go out of my way to compliment people now in similar situations, because I know how much of a difference a one-line compliment can make.”
An old friend
“Self-doubt (SD) is especially bad when I’m starting a new project. My first company was deeply personal and mission-driven but required a lot of upfront capital (like most of my savings). I was always pretty good at hyping myself up to start the project but then the flashbacks would come. I begin to think of my mom and the 14hr shifts she’s worked since 2002. I had been working towards affording her an early retirement at the time and SD reminded me that it could all go away in a second.
“One wrong move and I would revert our family back to poverty.
“It would be on me.
“These thoughts left me sleepless, and also [made me] lose excitement in other parts of my life too. It sucked but having gone through it, I now consider SD a friend. Not a friend I’d want to hang out with all the time but an old friend with good intention and zero sugar coat.
“I can be a reckless person at times and can trust SD to be there to remind me that I have a lot to fucking lose.
“It reminds me to be very careful and to hustle like I have everything to lose.
“Whatever causes SD’s intervention these days, I realize it must be really fucking important to me and worth a second thought.”
– Mya, Forbes 30 Under 30 Founder
When you lose
“Say I lose my biggest client and I start to be overwhelmed with self doubt, my go to thoughts / comments / narratives are:
Am I delusional about my abilities? Maybe I’m actually an idiot with an ego? Imposter
What if I had done this, done that. Every little time I wasn’t perfect becomes a possible moment that will come back to ruin me
I’ve always been unlucky and luck seems to be a big part of success, so maybe I’m doomed no matter what
“But then there’s also a deeper narrative:
Maybe I just don’t ACTUALLY want this. I just think I want this. And my soul just isn’t in it and therefore I will fail. I’m not self aware enough
We all die. Nothing matters… especially me and what I’m doing.
A lot of successful people seem miserable. Is this a rat race? Am i setting myself up to fail on what really matters
Overall inability to identify a reason for why I am doing something and why I am the one that can do it”
– Elijah, Venture-backed founder
Self-compassion
“When I think about narratives, I try to go back to the psychology of ‘self talk’–especially when it comes to reducing ‘negative self talk’. Through time, self awareness and an emphasis on reducing self criticism, has helped me to become less doubtful. The question of ‘Why are you doing this?’, if done with self compassion can be a great way to maintain focus and inspire creativity.
“In terms of negative self talk day to day, I try to look at things through the constructive criticism lens, rather than the self critic. The former allows for more creativity. Life can be a challenge, and patience with the process helps me to embrace more self confidence.”
– Zack, General Partner at Venture Firm/Podcast Host
When Zack shared this, I couldn’t help but recall Jack Kornfield‘s line, “If your compassion does not include yourself, it is incomplete.”
What’s next
“Great question.
“I wish I could be of specific help but I do not do ‘self doubt.’
“I have had many many many challenges and course changes in my life, but each one of them created a new path. There are times when I am disappointed that my path doesn’t go in the direction.
“I had originally predicted or hoped for, but I can’t remember ever feeling self doubt. That’s because I always know I will discover the way forward that does work for me in the moment. I tend to focus more on the ‘what to do next’ rather than the ‘why something happened.’ I tend to be very stoic in my assessment and dealings with challenges. I don’t like feeling bad so I tend to create plans pretty quickly to move through whatever challenges I have.
“I do my best to recognize progress and change and do my best to adjust to it as fast as possible in order to minimize discomfort. I also tend not to think of things as either good or bad… just events that happen. The only thing I know I have control of is my response to change. I can’t control much… including the tempo of change. I tend to not look backward as to ‘why’ things happen and focus on ‘what’ I may have done to cause them as well as ‘what’ I am going to do next. In essence, I don’t feel like a victim ever… I own the events and challenges I face and do my best to strategize how to move through them.
“One easy example is this past year. My business model of being an in-person speaker got turned off like a light switch. I then just kept moving and building relationships. I believe the choice we have is to either keep up with the tempo of change in the world or not.
“Another example is happening right now. This past year I began walking a great deal and listening to audible books, taking notes and creating content. It was very enjoyable. I injured my hip a few weeks ago and it has totally disrupted my routine. I am working as quickly as possible to create new routines and healthy habits to continue to live what I believe is my purpose. It sucks that things change, but that is inevitable :)”
– Liam, Former FBI, Author
Personal suffering as a proxy
When talking about mental health, Max Nussenbaum, Program Director @OnDeck Writer Fellowship, always comes to mind. When I pinged him for answers, he gave me the opportunity to quote some of his amazingly candid essays.
“I wrote two pieces on this, one about being a startup founder and the other about being a writer.”
Both of the above pieces I highly recommend. But here are a few of Max’s thoughts that resonated with me the most. Even then, this snapshot will not do the nuance he describes justice:
“Since I didn’t know how to prove to myself that I belonged where I was, I turned to the only method I could come up with: treating my personal suffering as a proxy. The rest of my life becoming less and less put together must have meant that I was throwing more and more of myself into the company, and therefore that no one—least of all me—could question my commitment or whether I was cut out for this. And so I partied too much and foreclosed any real connection with the people I was dating and just generally reveled in everything around me being a bit of a mess.”
“A lot of this was fun, but I was stressed and anxious all the time; there was both a euphoria and a terror in feeling like my life was moving so fast that the whole thing threatened to go off the rails at any moment. I would look around and think to myself, this must be what really living is all about. And whenever I felt like an imposter as a founder, I’d use the corresponding messiness of my personal life as proof that I was giving the company my all.
“Of course, none of this made any logical sense, and none of it made us more successful. A stable relationship almost certainly would have been a support system that helped me be a better founder; at the very least, it’s hard to do good work when you were out till 4 a.m. doing drugs with strangers the night before. But that’s the thing: I wasn’t optimizing for actually making my company successful. I was optimizing for assuaging my own insecurities.”
Doing your best
“In short, I have a simple approach for when self-doubt could come in – in that, as long as you believe you are doing the best you can, getting support from others to help get through the situation, and striving to continually improve, then what is meant to be, will be. If it doesn’t happen, then it wasn’t meant to happen and something that’s better suited for you will come along in due time.
“While it might be short term disappointment, either turn it into a driving force to do better and achieve what you were originally trying to do, but knowing limits, putting in a plan for constant improvement and being satisfied with the achievements as long as you can internally reflect and know you did your best.”
– Mateo, Head of International at a post-Series B startup
Your best days are ahead
“I grew up in a poor, uneducated family, and have for a long time felt like I didn’t quite fit in. To them, my curiosity and intellectual pursuits are deemed futile and a pipe dream. It has also been met with ridicule and mockery. As much as I pretend that it doesn’t affect me, ultimately the people in your family have so much influence on our sense of self worth. It wasn’t until moving out here in 2013, that I felt like I found my family and my tribe. That narrative still bounces around in my head from time to time, but I have worked really hard through therapy and conversations with mentors to eradicate a good majority of it.
“I guess imposter syndrome, is the widely used term for this condition. For folks like us, that may be more deeply rooted and takes more effort to overcome. Am I smart enough to do this? Do I know enough? Am I experienced enough? I’m not educated like my colleagues. I didn’t go to Stanford, Cal, or MIT. What am I doing here?
“There’s only so much one can tell oneself to overcome these deeply rooted self doubts, ‘you got this’ ‘you belong here’.
“I have found that working through it is a journey that involves creating new habits and forming new narratives. Turning the negative self talk into, ‘this is part of the process’ ‘your beginner’s mind is an asset’ ‘I’m not my highly educated colleagues, but my game and perspective is unique’.
“Growing up in South Carolina in my family, so many of the things the could have been cultivated weren’t, and that’s fine. I feel like my best days are ahead of me, and I’ll take that.”
– Harry, Senior Design Leader at a Fortune 100 company
The war between results and doubt
“Whenever I go a month or more without a sale, the doubt starts to creep in. The only thing that pushes the doubt away is a successful sale. I am better at dealing with it now because I have been through so many cycles and ups and downs, but I have never truly figured out how to eliminate the doubt (or better channel/repurpose that negative energy) that creeps in whenever I have a little capacity to do more work.”
– Lucas, Managing Director at an Executive Search Firm
Would she say the same for a man?
As if the world gave me the sign to take this leap of faith to write this blogpost, the first person I reached out to was Stephanie. I happened to catch her right at the moment she had been rejected after an interview for a senior position at a firm.
“I was honest about my career and life. Next time I could speak differently but I know with my resume and the time off I took that I would get the questions I received.
“I just hated the comment she made. She was very complimentary but then used this word that made me wonder, ‘Hmm would she say this about a man with my same career path?’
“The interviewer commented to my friend that I was smart but ‘too whimsical’ for the role they are hiring for. It made me question my whole career path for a second. By the way, I had never been called ‘whimsical’ before… that’s a word used for fairies.
“I try not to overstress myself and that’s why my personality is more chillax, but I take myself very seriously at work.
“Questions I ask myself and messages I give myself when I have doubt:
‘Am I doing the right thing with my life?’
‘What can I do to help others understand why I am taking this direction?’
‘How can I be my number one fan?’
‘Be compassionate with yourself.’
‘Focus on your mental health during this time of self doubt.’
(when someone rejects me)”
– Stephanie, Female co-founder of a hedge fund and advisor to multiple companies
Dreaming and falling
“From my own experience the question of self-doubt sneaks in way too often in almost any entrepreneurial quest. It can happen that you have self-doubt 101 times a day about some totally banal things such as ‘can I name myself a CEO and put it on my LinkedIn profile if I just founded a business’.
“For me personally, those ‘light’ self-doubt questions are categorized more as decisions. Same as with food, just make up your mind on what you want to have for lunch and stick to your decision whether it tastes or it doesn’t taste good. And of course, if it did not taste well enough, make sure that you have learned the lesson for the next time.
“The real heavy self-doubt comes to surface when:
A. You are selling a dream, a vision or an idea, and B. When things are falling apart.
>> A.
“In situation (a), it can often happen when you don’t have enough pieces of tangible evidence, data points, intelligence, etc. to prove your point of view to yourself and others. People will say – your idea sucks, this is impossible, you don’t have the skillset, your team is not good enough, the market does not exit, etc.
“To ‘survive’ these situations and be able to thrive no matter the negative comments and feedback (which often can come from some of the most influential and successful investors and entrepreneurs), I always make sure that before I go out there selling my vision, I truly believe in my idea/dream and that I have done enough homework to personally assure that there is a decent chance for it to come to life. I bulletproof it for myself first before I take that and test it with the world.
“Moving forward with selling the dream, during the conversations I tend to come back to the narratives of others who did something great in the past and proved others wrong.
“As Nelson Mandela would say, ‘It always seems impossible until it’s done.’
“I read so many inspirational stories of successful innovators, scientists, philosophers, artists, sport athletes, and entrepreneurs. And I don’t hesitate to bring those examples up in a conversation to show that someone has done it before even though at the beginning no one recognized their potential or the potential of their idea.
>> B.
“For situation (b) when your project is failing, sometimes it is totally out of your hands (and that is sort of an easier scenario,) but sometimes you do tend to question yourself if you could have done something differently. You start developing self-doubt in your managerial and entrepreneurial competence. Especially when you read so many headlines about the success of other entrepreneurs that raised 100s of millions or exited their companies at some mind-boggling valuations.
“In those moments, I do two things:
I rationalize by going back in the past and rewinding all the small achievements we made along the way. While doing that, I express deep gratitude for every single small step I made. As an example, we never raised from a Tier 1 VC but we met a lot of them and with some, we had multiple rounds of conversations. I am deeply grateful for even hearing back from them, for every moment they took to review my deck and learn more about our project. Success is the path and the process itself, not the final outcome. And that is what I remind myself of, in case the self-doubt comes to surface.
I ask myself if I did put in my perfect effort because that is all I could have done. As Sam Altman said, one needs a great idea, a great product, a great team, and great execution. Even if you have all four of these you may still fail. The outcome is something like idea x product x execution x team x luck, where luck is a random number between zero and ten thousand. Knowing that at the end of the day we are only in control of our thoughts, intentions, and reactions I end up asking myself – am I a satisfied with my input and work and did I do my best and put in the perfect effort? And the answer to that question brings me to a rationale that is beyond self-doubt and is actually the basic building block of self-confidence. This really helps to turn doubt into a strength!”
I know that not every story will resonate. Some may never resonate. Some will grow on you over time. Others will find meaning into your life when you least expect them to. My purpose for starting this blogpost is to freeze these stories and life lessons in amber for when you find yourself needing them the most. Life’s not easy. Neither is it meant to be. But hopefully, you’ll find comfort knowing you are not alone.
At the end of the day, all advice is autobiographical. Or as Kevin Kelly, co-founder of WIRED magazine, once wrote, “Advice like these are not laws. They are like hats. If one doesn’t fit, try another.” What you’ve read above are the advice, stories, autobiographies. Anecdotes that hopefully shed more light into the elements of humanity many of us, including myself, have been scared to talk about.
A good buddy of mine made me watch a movie recently. It couldn’t have been more timely. He told me nothing more than this one line from that movie:
“We are all the unreliable narrators of each other’s stories.”
So I watched it. I won’t tell you the name of the movie or what it’s about, but if you use the above quote in your search query, you’ll find it. And if you’re like me, and so many others, who struggle with identity and your place in the world – either now or in the past, it’ll change the way you see the world and the people around you.
Thank you Taylor, Max, Janko and everyone else who made this piece possible!
#unfiltered is a series where I share my raw thoughts and unfiltered commentary about anything and everything. It’s not designed to go down smoothly like the best cup of cappuccino you’ve ever had (although here‘s where I found mine), more like the lonely coffee bean still struggling to find its identity (which also may one day find its way into a more thesis-driven blogpost). Who knows? The possibilities are endless.
Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!
While I don’t always ask this question, when I do, it provides me enormous context to how the founding team works together. What do you and your co-founders fundamentally disagree on? Over the years, I’ve heard many different answers to this question. “We disagreed on which client to bring into our alpha.” “On our last hire.” “Our pricing strategy.” And so on. As long as you contextualize the point of friction, and elaborate on how, why, and what you do to resolve it, then you’re good. There’s no right answer, but there is a wrong answer.
The answer that scares me the most is: “We agree on everything.” Or some variation of that. While people may share a lot of similarities, even potentially the same Myers Briggs personality type (although I do believe people are more nuanced than four letters), no two people are ever completely the same. Take twins, for example. Genetically, they couldn’t be any more similar. Yet, to any of us, who’ve met any pair of twins in our lifetime know they are vastly different people.
Priorities lead to disagreements
One of my favorite counterintuitive lessons from the co-founder and CEO of Twilio, Jeff Lawson, is: “If your exec team isn’t arguing, you’re not prioritizing.” He further elaborates:
“As an executive team, we never actually argued — which is a strange thing to bother a CEO. But in fact, something always felt not quite right to me when we always agreed. Clearly, we must not be making good enough decisions if we all agree all the time.
“What I came to realize was that the reason why we didn’t argue is we weren’t prioritizing. One person says, ‘I like idea A,’ and the other person says, ‘I like idea B,’ and you say, ‘Great, put them both down, we’ll do it all!’ And in fact, when you look back on those documents at the end of the year, we rarely got around to very much of anything in those documents.
“Be vigorous not just about what makes the list, but the specific order in which priorities fall. “We realized it’s not just about all the things we could do, but the order of importance — which is first, which is second. Now you get disagreements and a lot of vigorous, healthy debate.”
Starting the tough conversation
Admittedly, it’s not always easy to have these tough conversations with the people you trust most. In fact, often times, it’s even harder to have these conversations because you’re scared about what it can do to your relationship. Arguably, a fragile one at best. At the end of last year, Yin Wu, founder of Pulley, shared an incredible mindset shift when building an all-star team, which led to my conversation with her.
3/ We are not a family. We are a world class team, purpose built to win. Most founder-types do not want a 2nd family, they want to excel.
We push each other to improve. We own our mistakes so we can avoid making same mistake twice. We celebrate our joint success as a team.
You’re a team driven to change the world we live in. And to do so, you need a system of priorities.
One of the best ways I’ve learned to address conflicts – explicit and implicit, the latter more detrimental than the former – is taking the most obvious, but the one that most people try to avoid. Address the elephant in the room at the beginning.
I love the way Elizabeth Gilbertapproaches that elephant, “The truth has legs. It’s the only thing that will be left standing in the end. So at the end of the day, when all the drama has blown up, and all the trauma has expressed itself, and everyone has acted up and acted out, and there’s been whatever else is happening, when all of that settles, there’s only going to be one thing left standing in the room always, and that’s going to be the truth. […] Since that’s where we’re going to end up, why don’t we just start with it? Why don’t we just start with it?”
When it hasn’t happened yet
If you haven’t disagreed with your team yet, you either haven’t established your priorities or one or the other or both has yet to bring it up. A mentor of mine once told me, “Whatever you least want to do or talk about should be your top priority.” And the goal is to sit down with your team and figure it out. To come into the conversation suspending immediate judgment and trying to see where your other team members are coming from.
As the CEO of a startup or a leader of a team, you don’t have to use every piece of feedback or input you get from your teammates. But you should make sure your teammates feel heard. That you’ve put thought and intention behind considering their ideas and opinions. Whether you choose to deviate from your teammates’ opinions or not, you should clearly convey the rubric that you used to make that decision. And why and how it aligns with the company’s mission.
In closing
And of course, the follow-up to the first question about disagreement would be: How often do these disagreements happen? And how do you move forward after the disagreement comes to light?
I go back to a line Naval Ravikant, co-founder of AngelList, once said, “If you can’t see yourself working with someone for life, don’t work with them for a day.” Indubitably, you’re going to be working with your co-founders for a long time. And if you haven’t dissented with your co-founders – or for that matter, other team members, investors, and customers – yet, you will. And knowing what, how and why you disagree with others can be invaluable for your company’s survival and growth.
This past weekend I heard a new phrasing of disagreement I really liked from a friend of mine. “Creative conflict.” I’m adding that phrase to my dictionary from now on. And well, this is my preface to you all before I do.
Prioritize. Communicate. And embrace creative conflict.
Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!
I recently tuned back into Elizabeth Gilbert‘s, author of Eat Pray Love, 2016 interview with On Being. It also happens to be one of my favorite interviews about creativity and curiosity. I found myself pausing, rewinding, playing, pausing, rewinding, then playing again one line again and again.
“Everything that is interesting is 90 percent boring.”
She further elaborates, “And I think one of the reasons that both my sister and I ended up being authors is because we were taught how to do boring things for a long time. And I think that’s really important, because here is one of the grand misconceptions about creativity, and when people dream of quitting their boring job so that they can have a creative life, one of the risks of great disappointment is the realization that, ‘Oh, this is also a boring job a lot of the time.’ It’s certainly tedious. It’s a boring job I would rather do than any other boring job. It’s the most interesting boring job I’ve ever had. […]
“And we are in a culture that’s addicted to the good part, the exciting part, the fun part, the reward. But every single thing that I think is fascinating is mostly boring.”
She takes it from a perspective that everything has its boring parts. So you have to learn to accept what’s boring along with what’s interesting. I think she’s absolutely right. But while I was tuning in again to that same interview – those exact same lines – for who knows, the 20th time, I thought… maybe there’s something more. Forgive my brain for having the tendency to jump into numbers and equations. That for some reason, one of the primary ways I understand life has to be through some quantitative lens. I thought, what if we take it from an expected value perspective.
Expected value = 10% * (Utility of interesting) + 90% * (Utility of boring)
The utility we gain from boring, often times, is of course, well… boring. Some utility value less than zero. Or in other words, more often than not, we lose utility. On the other hand, the utility we gain from interesting is positive. So, then it becomes a balancing act between what’s interesting and what’s boring. That in the decision to pursue something interesting, there might be the below subconscious calculus:
10% * (Utility of interesting) > 90% * (Utility of boring)
To shine a different light, is the interesting part interesting enough that it outweighs all of the boring parts combined, and ideally, more?
Take, for instance, writing for me. I love writing. It’s meditative. Thought-provoking. And it’s challenging. But at the same time, editing, filling in the keywords for SEO, finding a cover image, all the way to writing when I don’t feel inspired, but I do so to commit to a weekly routine is tedious.
Similarly, Gilbert uses the example of raising children. “Raising children — I’m not a mother, but I’m a stepmother, I’m a grandmother, I’m a godmother, I’m an aunt, and I know that 90 percent of — especially, being with very small children…
“Incredibly — it’s hard. And then there’s the moment where you realize, ‘Oh, my God, this is a spark of creation that I’m working with, and this is magic, and this is life seen through new eyes.’ And creativity is the same, where 90 percent of the work is quite tedious. And if you can stick through those parts — not rush through the experiences of life that have the most possibility of transforming you, but to stay with it until the moment of transformation comes and then through that, to the other side — then, very interesting things will start to happen within very boring frameworks.”
For many of this blog’s readers, it’s starting a business. Whether you’re changing the world or the people you care the most about, that mission is what drives you. That’s what makes it interesting. And every time you hit a milestone –
Your first user outside of your friends and family,
Rated #1 on Product Hunt,
One of your customers writes a handwritten love letter to you and your team about how you saved her family,
You finally have enough revenue to pay your team members who’ve been working with you for free for two years,
$1M in ARR,
50,000 users,
You reach profitability,
Your dream investor says yes,
A Fortune 500 business offers you 9 figures for your business,
And the list goes on and on.
… it’s exciting! But let’s be honest, not every day will be sunshine and rainbows. 90% of your days will be tedious. Some percent of those days or weeks might even suck! 90% of your days will be you working to find and reach that 10%. And if that 10% is just that amazing, it’ll make that 90% worth it.
In a sense, it’s like the Pareto Principle. 80% of your utility will come from 20% of your achievements. That star 20% – your customer love letters, providing employment for all your team members during the tough days of COVID.
In an analogous mental model, in everything that is boring, there might be a small percentage that makes it interesting. Now I’m really curious as to what I might discover here.
#unfiltered is a series where I share my raw thoughts and unfiltered commentary about anything and everything. It’s not designed to go down smoothly like the best cup of cappuccino you’ve ever had (although here‘s where I found mine), more like the lonely coffee bean still struggling to find its identity (which also may one day find its way into a more thesis-driven blogpost). Who knows? The possibilities are endless.
Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!
The other day, I jumped on a call with a friend who was going through a speed bump in his relationship. Though I’m no behavioral scientist nor expert in all matters regarding relationships, I’ve been privy to cousin cases between other couples, dorm-mates and roommates, as well as startup teams. And like most people out there, I’ve been through my fair share as well.
From my own experience, as well as from being a fly on the wall to others’, a large portion of the drama starts with the time spent dancing around the elephant in the room. And the longer a pair (or more) dances, the worse it gets. At the same time, it’s easier said than done. Rationally, we know that we should start with the truth. But frankly, it’s hard for many of us, myself included, to speak the truth when we need to. And in my hesitation, I usually regress to thinking: “Maybe it’ll get better over time. Maybe he/she will just forget about it. Maybe someone else will solve it in my place.”
Though I’ve gotten better at getting straight to the point, I’ve, by no means, mastered my approach.
“The truth has legs. It’s the only thing that will be left standing at the end of the day… And since that’s where we’re going to end up, why don’t we just start with it?”
The Boiling Frog Problem
As all drama goes, we end up beating ourselves and others up in the process. Yet, when the dust settles, we still come back to the one left standing. There’s a similar concept that I learned in a college business course called the boiling frog problem.
If you put a frog in boiling water right away, it’ll jump out. But if you put the frog in lukewarm water and slowly heat it up, it won’t notice until it’s too late. And for the sake of the analogy, end up dying in the latter case.
The emotional turmoil we go through in our daily lives is no exception. It’s much easier to address the problem from the get-go, then let it rot you inside out. To put it into perspective, let’s say you address the problem at the beginning. There are only two outcomes possible:
It’s not as bad as you expected, and you’re able to resolve it easily.
It’s just as bad as you thought it’d be (as your mind regresses to the worst case possible). And well, you get burnt, as expected. But you will come out as a stronger person than when you went in. A phoenix reborn.
In closing
In tricky times, many of our relationships have been put on the rocks. The important part isn’t the conflict itself, but how we resolve the conflict. A frame of mind where there is no blame to dish out, but taking mutual responsibility to come out stronger in finding the resolution. Mike Maples Jr, co-founder of Floodgate, one of the most successful VC firms in the Valley, once said:
“Ego is about who’s right. Truth is about what’s right.”
