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We hear a lot about self-discipline in todays productivity-obsessed culture. And the message is usually that its the cure for economic insecurity and a pathway to self-actualization. At first glance, this appears to make sense. But it can be a double-edged sword in our modern work lives and always-on culture. Self-discipline enables focus and is key to achievement. However, over-indexing on it can easily erode our own values and boundaries. In turn, this can cause burnout, isolation, and existential despair. What does discipline really mean? Discipline has historically been associated with punishment and religious correction. Think physical punishment, including self-flagellation. I grew up at a time when well-meaning parents dispensed discipline, thinking thats what it would take to raise virtuous children. The payoff that came with being praised for hard work at school and excelling in sports meant discipline became a core aspect of my early self-identity. Contemporary examples of personal discipline tap into the human capacity to regulate impulses and persist toward long-term goals. We see many influencers create vast content parading their self-discipline, whether thats adhering to a complex, three-hour morning routine, or proselytizing an extremely restrictive diet. As a result, self-discipline has taken on a moralistic, “holier-than-thou” tone, with the inference being that doing anything less means you are weak, lazy, and unworthy. The overt benefits of discipline at work Amid extreme uncertainty, self-discipline can serve as a powerful protective asset. Longitudinal research on self-control shows that those who can delay gratification and regulate impulses tend to achieve better educational outcomes, higher income, and improved health indicators. Another research paper suggests that self-discipline can reduce procrastination by boosting autonomous motivation rather than relying on willpower. When people experience their discipline as self-chosen and values-aligned, they report greater feelings of competence and autonomy. In the current work landscape, disciplined routines can help us create a sense of control and continuity amid relentless structural volatility. When discipline becomes addictive and isolating However, the same traits that fuel achievement can become compulsive and harmful. Eventually, excessive discipline can lead to ego depletion, where subsequent acts of self-control become harder and more draining. In cultures that moralize productivity, this depletion can be misconstrued as personal failure. As a result, many end up doubling down on discipline rather than questioning the demands theyve been subjected to. This was my experience as a corporate finance lawyer. At first, the self-discipline Id learned early in life translated perfectly into the “magic circle” law firm culture. Eventually, the constant, intense workload wore me down. Finally, I collapsed at an airport in a state of exhaustion and emotional despair. As uncomfortable as this was, it also gave rise to deep relief: I no longer had to punish myself. Discipline can become addictive when it produces rewards, but eventually, discipline can become an identity in itself. You might start holding beliefs like having needs is weak, I need to override my bodily urge to rest, or if I falter, I am a failure. This can lead to anxiety around rest, spontaneity, or deviation from a meticulous schedule. Proponents may begin to choose habits and work patterns that reinforce their disciplined self-image. They stay at the desk until deep in the night, or fasting for an extra day just to prove they can, even when these conflict with relational needs, leisure, or health. This kind of self-discipline can foster isolation in three ways: Time-intensive routines (early mornings, extended work hours, strict fitness or side-hustle regimes) crowd out social life and community participation. They avoid relationships or spaces that “threaten” routine, and they end up narrowing social worlds to similarly disciplined peers, or online productivity subcultures. They believe that we have sole responsibility for our station in life, rather than seeing the broader, systemic issues. This can cause us to internalize blame, which leads to shame, loneliness, and low self-worth. Discipline as a modern-day comfort blanket The definition of our current moment is a paradox: intensified individual responsibility amid abject structural insecurity. Theres an expectation for us to optimize every facet of our lives: our skills, our bodies, and our relationships. This has two major implications. First, we engage the language of discipline to obscure the structural causes of success and failure. We see unemployment, underemployment, and burnout as deficits of willpower rather than outcomes of policy, corporate practice, or macroeconomic conditions. Second, self-care industries, while at times genuinely beneficial, individualize the management of systemic stress. As a result, this capitalizes on widespread alienation to the detriment of most for the benefit of a few. We see this dynamic play out for knowledge workers and founders in particular. Hustle culture normalizes permanent availability, constant upskilling, and the erosion of boundaries between work and non-work, all in the name of disciplined ambition. The result is another paradox: The very discipline that enables career advancement may also entrench the conditionsoverwork, anxiety, weakened social tiesthat undermine our long-term wellbeing and creativity. Toward a more humane discipline Tempting as it feels to jettison self-discipline altogether, we have a powerful opportunity to reclaim the term. A more humane approach would treat discipline less as an austerity project and more as a tool for protecting your time, energy, and attention for what genuinely matters to you. A good name for this term is mindful self-discipline. Practically, adopting mindful self-discipline means taking a few steps: Self-Knowledge: Get really clear on who you are and what matters to you. Not to your parents, peers, society, colleagues, or rndom influencers. For many, this requires peeling back the layers of values and ideas weve taken on, often subconsciously, and identifying our own core values, needs, and priorities. Self-Awareness: Use discernment to employ disciplined behavior around boundaries, rather than endless productivity. Limit work hours, design your downtime as nonnegotiable, and actively resist the pressure to optimize every waking moment. Self-Compassion: Ensure that your motivation for pursuing your work, hobbies, and other activities in life doesnt come from the belief that youre lazy, unworthy, or weak. Foster strong self-beliefs around your own intrinsic value as a human being to protect yourself from any harmful self-discipline narrative. Mindful self-discipline can be used as a strategic resource to carve out autonomy and dignity. The task for all of us is to ensure that human discipline serves our individual and collective flourishingrather than diminishing the very same.
Category:
E-Commerce
When I tell fellow tech executives that every employee at sunday, from our engineers to our finance team, must complete a restaurant shift before they can fully onboard, I usually get confused looks. “You mean like, shadow someone?” they ask. No. I mean they tie on an apron, take orders, run food, and yes, deal with the 15-minute wait for the check that our product was literally built to eliminate. It sounds extreme. It is extreme. And it’s also one of the smartest business decisions we’ve made. Here’s why: business is often removed from the industries we serve. Were keeping that empathy right there. The Empathy Gap in Tech I’ve spent 25 years in the tech world, scaling e-commerce unicorns in Europe before cofounding sunday. I’ve seen brilliant engineers build elegant solutions to problems they’ve never personally experienced. I’ve watched product teams debate restaurant workflows they’ve only seen in wireframes. The result? Products that work in theory but fail in the chaos of a Friday night dinner rush. Using our industry as an example, the restaurant space cant be disrupted from a distance. It’s intensely human. A server manages six tables, remembers who wanted dressing on the side, tracks which kitchen orders are running late, and still needs to radiate warmth when checking on the anniversary couple at table twelve. When we ask them to adopt new technology, we’re not just changing their workflow, we’re asking them to trust us with their tips, their table turn times, and their relationship with guests. You can’t design for that kind of stakes without understanding them viscerally. What a Saturday Night Shift Teaches a Software Engineer Last month, I watched our newest engineer finish his restaurant shift at one of our partner locations. He was confident going in; he understood our API integrations, he knew our payment flow inside and out. But after five hours on his feet, he had a revelation. “At the end of my shift, I had to manually enter tips from 22 tables into the POS system,” he told me, exhausted. “Twenty-two times typing in amounts, double-checking I got the numbers right, worrying I’d accidentally shortchange myself or mess up the restaurant’s accounting. The whole time I’m thinking about the train I’m about to miss, and I’m doing math in my head to see if my night was even worth it. It took 15 minutes of my life I’ll never get back.” This wasn’t theoretical anymore. “I finally understood what we’re actually saving people from,” he told me the next day. “It’s not just 15 minutesit’s the mental load of worrying you made a mistake, the frustration of doing data entry when you’re exhausted, the indignity of technology making your life harder instead of easier. When I use sunday now, I know exactly whose time I’m giving back.” That’s the point. Empathy at scale isn’t built through user research reports. It’s built through experience. Hospitality as a Business Philosophy What started as a practical requirement has become central to how we think about everything at sunday. Hospitality isn’t about being nice. It’s about anticipating needs, moving with urgency, and making people feel valued even under pressure. Those principles translate directly to how we run our business. When a restaurant partner calls with an issue, our support team doesn’t respond with ticket numbers and SLAs. They respond like servers handling a complaint: with immediate acknowledgment, genuine concern, and a bias toward solving the problem now rather than escalating it later. Our customer success team knows that “I’ll get back to you tomorrow” is the tech equivalent of “your food will be out in a few minutes”a polite deflection that erodes trust. We’ve also borrowed the restaurant world’s obsession with the guest experience. In hospitality, there’s no such thing as “that’s not my table.” If a guest needs something, you handle it. We’ve tried to instill that same mentality. When a new market launch hits a snag, our engineers don’t wait for the ops team to flag it. When a sales issue arises, our product managers jump in. We move like a restaurant team during a rushfluid, collaborative, and focused on the experience we’re creating. The Metrics That Matter Here’s what surprised me most: this policy has become one of our best retention and recruiting tools. We’ve had a 94% retention rate among employees who complete the restaurant shift program, compared to 78% at my previous tech companies. Employees consistently rank it as one of their most valuable onboarding experiences. New hires tell us they appreciate working somewhere that values understanding over assumption. They like that leadership doesn’t just talk about customer obsessionwe quite literally make them walk in our customers’ shoes (and sensible non-slip ones at that). And when we hire, the restaurant shift requirement self-selects for people with the right mindset. Candidates who balk at the idea of working a shift often aren’t the right fit for our culture anyway. The ones who light up at the challenge? Those are our people. The tech industry loves to talk about disruption, but we’re often remarkably detached from the industries we claim to understand. We optimize for what we can measure: clicks, conversions, load times. And we miss what we can’t, the relief on a server’s face when they don’t have to chase down a credit card, the gratitude of a mom who can split a check without asking for help, the pride a restaurant owner feels when their team has more time to create memorable moments. Making our employees work restaurant shifts isn’t a cute culture quirk or a team-building exercise. It’s a business imperative. Every hour our team spends in a restaurant is an investment in building a product that actually solves real problems, not imagined ones. A Challenge to Tech Leaders I’d encourage every tech CEO, especially those building B2B products, to ask yourself: When was the last time you personally experienced the problem your product solves? Not observed it. Not read about it in research. Actually lived it? If the answer is “never” or “it’s been years,” you have a dangerous knowledge gap. Your team is making decisions based on assumptions, building for personas instead of people, and probably missing opportunities that would be obvious to anyone who spent a day in your customers’ reality. You don’t need to make it a formal policy like we have. But you do need to close the empathy gap between your builders and your users. Shadow a shift. Take customer service calls. Use your competitor’s products. Do whatever it takes to remember that behind every user statistic is a human being trying to do their job, feed their family, or simply have a nice dinner without waiting 15 minutes for the check. At sunday, we’ve learned that great technology in the hospitality space doesn’t come from brillian engineers alone. It comes from brilliant engineers who’ve burned their hand on a plate, forgotten which table ordered the gluten-free option, and felt genuine panic when the payment system hiccups during a Saturday night rush. That’s not just good culture. That’s good business.
Category:
E-Commerce
So, youve finally done it. No more putting it off, pushing through the grind, waiting for a more opportune time once things settle down. Alas, youve mustered up the gall to cash in on your paid vacation time. Now you have several days strung together to travel, rest, or do whatever the heck your heart desires. I love that for you. But before you slam your work laptop shut and Yabba dabba doo! your ass out of the office, theres one last thing. Youve gotta leave behind a message letting folks know youll be gone. You need to draft an out-of-office message. Out-of-office notes tend to be pretty standardcourtesy auto-replies letting folks know youre not working, when youll be back, and who, if anyone, they can contact in your stead. Sometimes people add a pop of color hinting at a life outside the office. But these things generally tend to be pretty vanilla. I, for one, wish corporate peeps got more real with this messaging. Treat these notes like early-stage Facebook status updates: Share what youre really thinking, feeling, and experiencing. This year is already a mess; immigrants continue to be targeted by the federal government, unemployment numbers remain dismal, and it seems like everyones got the flu. Why not keep it 100 for whoever reaches out in the interim? Longtime readers will remember when I presented a list of pandemic-era openers as alternatives to I hope this email finds you well. Here are some OOO notes I wish I had the heart to schedule. Deploy at your own risk. I am currently out of office, taking advantage of PTO that is technically unlimited but spiritually frowned upon. I am currently out of office, taking advantage of PTO that is technically unlimited but managerially frowned upon. I am currently out of office to recharge after running on vibes, caffeine, and anxiety for six consecutive quarters. I am out of office avoiding the news for my mental health. Please do not forward any think pieces. I am currently out of office closing the approximately 637 tabs I have openboth literally and mentally. I am currently out of office, wearing a quarter-zip sweater and drinking matcha. I hope this auto-reply finds you doing the same. Im OOO using the gym membership I will abandon by February. I am currently out of office, ignoring my inbox like its a group chat that is doing the most while Im trying to do the least. Ill be out of the office while my outie binge-watches Severance and realizes this job feels familiar. Upon my return, the work will continue to be mysterious and important. I am currently out of office, unpacking last year with a licensed professional. I am currently out of office, pondering the spiritual meaning of six-seven. I am currently out of office, updating my résumé just in case. I am currently out of office, rewatching Sinners so I can feel something again. I am currently out of office but will absolutely read this message anyway and respond once my brain stops buffering. I am currently out of office and launching my side hustle. Please subscribe to my Substack. I am currently out of office, but will be bumping that new A$AP Rocky album until further notice. Im OOO until my burnout is no longer a personality trait. I am currently out of office pivoting to my new self. Lets table this and circle back in Q2, when I have the bandwidth to get my ducks in a row. I am currently out of office, but dont expect a response as soon as I get back. Ill need a few days to remember how to do my job. I am currently out of office, but unfortunately still mentally available.
Category:
E-Commerce
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