The Messy Middle: Finding Your Way Through the Hardest and Most Crucial Part of Any Bold Venture
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Jeffrey then posed the same list of features and projects to his development and design teams. Once again, he asked them to assign a ranking from 1 to 3 for everything on the list. For this group, he requested that a 1 be assigned to every item that could be done quickly by a small group of people, a 2 for items in the middle that demanded more than a few days but less than a few weeks, and a 3 would be reserved for items that would take significant time and labor to complete, three weeks and up. With both columns filled out for all features and projects, Jeffrey scanned the list for 3/1s—the ...more
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Having worked with Apple’s marketing and keynote production teams quite a bit during my tenure leading mobile products at Adobe, I was struck by how carefully Apple decided what to reveal and when. Even after a product’s announcement, the reveal of every edge, angle, and aspect was intentional and restrained. As my friend, entrepreneur, and early Apple product designer Dave Morin once told me, “Mystery makes history.” When you leave something behind the curtain, people are more desperate to see the full picture.
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“In preparing for battle, I have always found that plans are useless, but planning is indispensable.” So said Dwight D. Eisenhower, and his words ring true today in how we approach all kinds of bold ventures.
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“In the case of friends, I will often ask, if someone asks me to do something, ‘Zero to ten, how much are you asking me to do this? Because if it’s a ten and you need me to do this, I will do it, but I have very little bandwidth right now so let me know. If it’s really, really important to you, I will do my best to help and move things around, but if not, I’ll pass.’ True friends, nine times out of ten, will give you a pass.
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I recall Andrew Wilkinson and Jeremy Giffon, partners at Canadian tech and design studio Tiny, summarizing the idea of successful entrepreneurs giving advice to others as the equivalent of someone saying, “Here’s the numbers I used to win the lottery.”
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The best advice doesn’t instruct—it provokes. The benefits of soliciting wisdom from others is indisputable, but the real value of advice comes from reconciling its contradictions.
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When everyone thinks you’re crazy, you’re either crazy . . . or really onto something.
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If you plan to move an industry forward in any material way, you must learn to gain confidence from doubt.
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What they’re missing is that history repeats itself until history is made by those who are informed but not bound by the past.
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“There’s a question we should ask every day: Are we investing our time in the most important things? . . . Simple back-of-the-envelope calculations will help you prioritize features according to their return on investment, making sure the outcomes are the highest possible over a given period of time.”
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Routines backfire when you start doing them without thinking. Throw a wrench in the machine every now and then.
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As part of the National Day of Unplugging, the group refined the “Sabbath Manifesto for the 21st Century.” The manifesto included ten principles for an effective break from the modern world. They are as follows: Avoid technology Connect with loved ones Nurture your health Get outside Avoid commerce Light candles Drink wine Eat bread Find silence Give back
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Be aware of the cost of constant connection. To keep perspective and nourish your imagination, create windows of nonstimulation in your day, rituals for disconnection, and periods of time in your life where you get out of your element and allow for new questions and curiosities to take hold.
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Nothing corrodes the potential of a team faster than a sense of superiority. Opportunity is lost as soon as you devalue those around you and embellish your own capabilities.
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On an interview for the Song Exploder podcast series, where artists unpack the creation of one of their songs, Weezer front man Rivers Cuomo described the creative process behind the song “Summer Elaine and Drunk Dori,” for which he wrote the original draft of the lyrics and score. I was struck by the handoff he described, in which he let his bandmates play with the first version of his song without him in the room. “I really appreciate the power of democracy,” he said. “The songwriter—in this case me—with the best of intentions can limit the creativity of the other members of the band because ...more
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To tap the full potential of your team, sometimes you have to let go of the reins and let people have their own creative process. Even if you think your first draft is perfect (unlikely), allow your colleagues to play with an idea without your presence. This fosters a sense of ownership and alignment that expedites execution. More often than not, great ideas grow out of good ideas—and it keeps the band together.
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Getting attention is distracting. In the early stages of a venture, one of the greatest benefits of isolation and anonymity is uninterrupted focus. The time a well-known and in-demand person spends fielding inquiries or reading about themselves online is time that you’re not spending on building their team and product, planning, and learning.
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Earlier, when we explored tactics for optimizing products, I explained the importance of “ego analytics,” the stuff that feeds an early user’s vanity enough to engage them and keep them coming back, whether it be “likes” from their friends or a leaderboard in a game they are playing.
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For six months we worked late nights after our day jobs, mocking up and debating the plans for Behance over bottles of wine and Chinese takeout. And now, seven years later, it was all coming to an inflection point that would change our lives.
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When you walk around the headquarters of Facebook, a company known for its “stay scrappy” ethos, you’ll notice the persistent presence of stickers on laptops and sayings on posters that read THIS JOURNEY IS 1 PERCENT FINISHED.
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Sustaining the “we’re still just getting started” mentality keeps people questioning assumptions and always thinking bigger.
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As you approach the later stages of your project, your challenge is to hold on to some of the openness, humility, and brashness you had in the beginning. Keep repositioning the ultimate goal to be as far away as you can see, and never forget that blind spots only grow as you succeed. In mind and in spirit, stay in the early innings.
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But the entrepreneurs I respect the most own their outcome, no matter what it is. They end gracefully.
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As an investor, I look for entrepreneurs who are empathetic, have a set of customers suffering from a problem, are deeply passionate about solving it, are self-aware, and have been weathered from some real-world experiences that will help them endure and optimize the journey ahead.
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Whether it is a musician feeling forever defined by his band’s success a decade ago or a business leader known for a particular venture earlier in her life, great work tends to hijack one’s sense of self.
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So, that’s what it looks like to end on your own terms, I thought to myself. It’s not just about moving on when you’re performing at the level you always wanted to be remembered for—the desire to “end on a high.” It’s about moving on when you feel fully satiated and can therefore allow yourself to pursue something different.
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It wasn’t an easy decision, but he felt fulfilled by his work and noticed his energy and interests beginning to shift elsewhere. Rather than wait until his work started to suffer, he made the decision.
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That’s how knowledge works. It builds up, like compound interest. All of you can do it, but I guarantee not many of you will do it.”
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More than one mentor has told me that the ultimate achievement is being able to spend your time as you wish.
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