Lead from the Outside: How to Build Your Future and Make Real Change

Chapter : Dare to Want More

  • Once we accept that we deserve to want more and we understand how giving birth to ambition requires knowing ourselves better, we're ready to actually start figuring out what lights us up and then plotting out our pathways to get it.
  • Because I didn't know people who had grand dreams, moving beyond make - believe seemed harder and harder as I grew older and games lost their allure.
  • Logic is a seductive excuse for setting low expectations. Its cool, rational precision urges you to believe that it makes sense to limit yourself. And when your goal means you'll be the first, or one of the few, as I desired, logic tells you that if it were possible, someone else would have done it by now.
  • Embracing ambition means learning not to listen too closely to anyone.
  • Ambition should be more than a title or a position. I'd focused on the what, not the why, and for more than a decade, I organized my life around that what. I understand now that knowing the real reason for your ambition allows you to figure out if a different path will get you there.
  • Realizing the why of my ambition allowed me to alter course and explore new roles that could accomplish the outcomes even more effectively.
  • Give yourself the space to explore why you don't know what you want.
  • When you decide what you want and why you want it, take action immediately. Do not wait for an invitation to act.
  • If you can walk away for days, weeks, or years at a time, it is not an ambition; it's a wish.
  • We tend to measure our passions by their likelihood of success, not the joy and excitement they bring.
  • Fear is a paralyzing force that twists deep in the gut, churning out anxiety and reasons not to act. Its seductive logic convinces us that now is not our time and winning is not our right.
  • Conditioning doesn't just happen to us, it happens around us, touching everyone and everything.
  • We learn not to want, not to expect, because we're trained not to see ourselves as more than what we've been told to be. Thus, fear becomes as familiar as air, an automatic caution against bucking the system.
  • For minority leaders to move forward, we must oftentimes first confront layers of anxiety holding us back.
  • We must name what scares us and acknowledge what scares those who are afraid of us.
  • A deep apprehension for many of us is the stereotype threat : the idea that we will always be judged by the worst example of someone in our community.
  • How do we retain a sense of identity without abandoning the true similarities shared with our kindred groups?
  • Wanting more than we're supposed to forces us to confront not only the possibility of failure but also the responsibility of success.
  • Fear is a common obstacle. Men experience fear " even white, powerful men who have rarely known the word "no. " But for the marginalized groups " those whose skin tone, gender, geography, or bank account signals "lesser than " , it can become a permanent companion eating away at confidence, ambition, relationships, and dreams.
  • Navigating power is difficult enough without adding the dimensions of otherness to the mix, but that's our reality.
  • Demonstrate to those in power the value in our difference.
  • For minority leaders, we often operate first as representatives of our communities, only tangentially as individuals.
  • Disappoint with deliberate care.
  • If you think you were right to behave as you did, then own it and move on. But do not avoid the internal investigation, however painful it might be.
  • Embracing your authentic self means being clear about how you wish to be seen. This doesn't mean feigning a personality that is artificial and then cutting loose at home.
  • It means bringing forth who we really are while being acutely aware of our surroundings.
  • Engage. I do not tell self - deprecating jokes about my race or gender, though I will do so about my personal idiosyncrasies.
  • Part of the job of leaders is to show why difference doesn't have to be a barrier.
  • We don't ignore the fear of others. We understand it and harness it to our advantage.
  • I'd never be invited into smoke - filled rooms or to the golf course, I instead requested individual meetings with political colleagues where I asked questions and learned about their interests, creating a similar sense of camaraderie.
  • The results should speak for themselves, but they do not always shout loud enough to drown out the objections.
  • Self - made is a misnomer, a stand - in for a more complex narrative that includes the ability to work for no pay, to borrow from friends and family, to experiment and fail without falling too
  • Despite the American fascination with the gutsy move, society is more likely to punish rather than praise those of us whose performances stray from a prescribed plan.
  • We have to first deconstruct the fictions of golden opportunity and realize not all worlds operate the same.
  • We aren't going to win playing by the written rules.
  • Doing exactly what we're told, amassing the education and the accolades and the experiences, guarantees absolutely nothing.
  • Once we understand our ambitions and learn how to admit and manage our fears, the next step is putting these lessons to work to find opportunity and own it.
  • Own opportunity and write our own story.
  • Confronting issues of access requires that you know where to look for the work - arounds or how to create your own. The second part, entry, means discovering the passwords to get inside.
  • In the wake of the elections, dozens of groups sprang up to encourage marginalized communities to take action and run for office. These groups are perfect examples of uncommon points of access.
  • By only hiring those I knew, who had been picked by others who knew them, I wound up with a team that looked exactly like those who preceded me.
  • Take too big a risk and you might lose what you have and not latch on to anything new.
  • Beyond interning, one often overlooked hack for moving up is volunteering as a way to get inside an organization, then making the most of that position.
  • One key approach is to cultivate relationships with those who have information and are typically ignored.
  • I am always genuinely engaged with support staff wherever I work.
  • The power of the invisible workers, hose whose knowledge may sometimes exceed that of the boss with the massive paycheck.
  • we often play down our capacities, thinking we are being humble, when humility has little to do with our hesitation.
  • Self - doubt is vicious and corrosive, transmitting internalized messages that say we lack something essential for true success.
  • often disguises an embarrassment about ambition and a lack of self - confidence.
  • Owning opportunity can feel like standing on a rickety ladder reaching for something on a higher shelf, knowing all along that, with one wrong move, everything could fall.
  • When we doubt ourselves into inaction, that paralysis becomes a habit.
  • Her graduation from college had been difficult, more “ thank you lordy " than “ magna cum laude. "
  • Regardless of how we get in the door or up the ladder, we can never forget that the expectations for us are not the same.
  • Whether the bona fides come in the form of advanced education, respected training courses, or job titles, be prepared to show your credentials.
  • Beyond the paper endorsements, real live validators are the most critical prospects for advancement. Be certain others are willing to sing your praises " to you and others.
  • reason, I have a regular habit of asking a small group of trusted friends to perform an informal - degree evaluation of me.
  • you also want to be certain these folks will tell others about you, particularly if they are sitting in rooms to which you have not yet gained entry. These supporters can explain you to the powers that be.
  • We need to be in it for others like us.
  • When no one in a poor neighborhood owns a business, the idea of entrepreneurship scarcely takes root.
  • We are, by our natures, often required to manufacture our own breaks, identify new openings even before others know they exist. The best hack is to know this is the case, accept it, and move on, prepared to take full advantage.

    Chapter 3 : The Myth of Mentors

  • Not used to management, I valued substance over style, giving out assignments but rarely engaging in social conversation, coming across as brash and unfriendly.
  • I made it a point to learn a new personal fact about each employee and to ask about their weekends before jumping into an assignment.
  • Instead of summoning staff to my office, I would walk to theirs to connect.
  • Once you've decided to fire someone, she warned, the kindest action is to be swift and final. Don't offer false hope or try to assuage your conscience.
  • Too often the idea of a mentor is a self - limiting device that has most of us hunting for someone we'll never find because of access or because our chosen guide already has a waiting list.
  • This is a professional courtship, so ease into it. My business partner, Lara, is fearless about reaching out to those whose careers pique her interest ; thus she has cultivated one of the broadest networks I've ever seen. She maintains quality relationships by calibrating her outreach based on the preferences of each person.
  • we became friends and business partners because she heard me speak at an event, and she reached out to me to learn more. And a peer mentorship was born.
  • A good mentorship network has a number of advisers with specific profiles.
  • A good adviser should offer a contrasting view
  • Because we do not share identical life histories, his perspective gives me a window into how to filter discussions and sift through my own readings of events.
  • Add in someone who has skills you admire.
  • Building real connections that make up a broad network is most effective when you learn how to be helped. With the proliferation of the mentor myth, I find too many have false expectations of the relationship. More than once, I've been asked to be a mentor, as though there's some “ mentor handbook " with a set of instructions. Worse, those who ask to be mentored tend to have only a vague notion of what they want. Fundamentally, the responsibility is on you, as the mentee, to create the mentorship that you want and manage expectations, especially your own.
  • You want to be aggressive in your curiosity. Ask important questions that you need answers to that you can't find anywhere else.
  • Don't wait for them to offer aid. Ask for what you need.
  • It is your responsibility to affirmatively ask for engagement and support. Do not drop hints; they'll lie on the ground forever.
  • Do not extrapolate : a "no" or a failure to help on one issue should not lead to an existential crisis about the relationship.
  • The worst reaction is to spin out a false theory rather than gain useful information.
  • People tend to help those who are open to helping others, not those who help themselves.
  • if you see a turtle sitting on a fence post, you know he didn't get there alone.
  • Professional friendships should not be mistaken for slumber - party friends. Professional friendships can also seem more transactional, but that's not always a bad thing.
  • Generosity in our engagements transforms who we are and expands where we can go.
  • We mistake income for wealth, not understanding the difference until too late.
  • Women and people of color find themselves accused more often of potential corruption driven by nothing more sinister than unexpected success.
  • Command of financial lingo and the dexterity to read and understand the spreadsheets and balance sheets behind institutions dramatically alters our authority and potential.
  • When we master the art of raising money across the board, we are prepared to move from participant to leader.
  • To get out of debt, consider the side hustle.
  • Entrepreneur magazine had a great list of options for the side hustle :
  • The takeaway : the difficulty of catching up and moving forward isn't all in your head. Systemic biases, legacy barriers, and current explosions of inequality conspire constantly to undermine wealth generation among minorities, especially women in these communities. But, as with all obstacles, our obligation is to acknowledge they exist and then fight like hell to subvert and circumvent them.
  • The more we understand, the more power we possess. Learning about the finances of a company or an organization is like learning a secret code.
  • Know how to effectively manage budgets and raise funds for projects are usually the ones calling the shots.
  • Terrible choices are often cloaked in the seemingly impenetrable world of finance.
  • Fund - raising is essential to success. Yet women and people of color or those who do not come from money often botch the ask or refuse to make it in the first place.
  • My first piece of advice : do not go it alone if you don't have to. I have usually started my businesses with a partner, based on the strong belief that I'd rather have percent of something than percent of nothing.
  • You also need to get specific. Not only should you try to know different types of people, you and your partners must know how much money you need to raise. Understand intimately what you want the money for, and you should have a clear, well - constructed plan. Be familiar with your details inside and out. No room for "umms" or vagueness. When making an ask, you usually only get one shot unless the person with resources finds your story or product compelling.
  • While I wouldn't recommend a barrage of asks or a hard sales pitch, engage them to seek out counsel and advice. Allow an organic conversation to develop. Often, these conversations reveal if they possess a hidden capacity to support your endeavor.
  • "Never tell yourself no. Let someone else do it."
  • The more we know, the better we get and the more we can control for our destinies and the world around us.
  • A central tenet to success is to show up " again and again and again " to take an alternate approach, and keep at it until it works.
  • The habit of not going beyond others ' expectations can transmute self - awareness, until the meek begin to believe they are less than.
  • we must cease being participants in our own oppression.
  • Harriet Tubman once declared, "I freed a whole lot of slaves. I could have freed a whole lot more, if they'd only known that they were slaves. "
  • Sam's preparation to win, his refusal to wait his turn, and his boldness in asking for and working for our help are pitch - perfect examples of how to prepare to win.
  • Timidity warned me that at only twenty - eight, I had never run anything as large as the division she described. Meekness urged me to demur, as I had no municipal legal experience. And logic demanded I not give up my private - sector salary for a city job. But boldness, the willingness to take risks, and the drive to do the hard work of learning this role demanded I say yes. So I did.
  • Crossing bright lines, being bold, has consequences. Not everyone will embrace the more aggressive you. The backlash might be subtle, like no longer being invited to participate in events or meetings. Or it could be starker, like a blocked promotion or a termination, or losing an election.
  • if you are bold, you will alienate others. There's no way around it. The best approach is to plan what you are going to do. Not only plan your action and anticipate the reaction, but then think through what you are going to do with what you've done.
  • Boldness lies not simply in having the thought but in claiming ownership, accepting responsibility for moving it forward, and then dealing with the consequences. Prepare to win, but also prepare to fail, always using boldness as your guide.
  • Risk taking inevitably leads to missteps or bad decisions. Unfortunately, admitting mistakes is a fundamental skill too few of us learn.
  • some people have thirty great years but others have the same crappy year thirty times.
  • Knowing how to be wrong is fundamentally about honing the ability to admit that you don't know.
  • I have learned lots of ways to say, “ I don't know. " My favorites are, “ I have some ideas, but let me do a bit more digging " and “ Here's what I think, but I could be wrong. I'll check. " Or I direct the person to the proper authority and I make the introduction myself.
  • The best way to admit you don't know is to always couple it with a way to find out.
  • We have to be careful who we ask for help or to whom we admit ignorance.
  • in every facet of our lives, if we are willing to risk, we will lose.
  • We create change when we eschew the instinct to only play when we know the outcomes.
  • One of the best things about being in the minority is the fact that limited resources often lead to extensive creativity.
  • At the core of leadership is the issue of power " the ability to secure what you need and the capacity to influence others to help you get
  • We cannot fight a war with resources we don't possess " so we must inventory what we do have and figure out how to use them in unexpected ways.
  • examine everything and leave nothing out.
  • understand the difference between position and power.
  • Access to real power also acknowledges that sometimes we have to collaborate rather than compete.
  • authentic leaders know what we believe and why, in order to have a clear sense of our direction.
  • one of the aspects of holding power is understanding the long game "
  • sometimes, a single act of defiance raises awareness and action,
  • But the creative ability of minority leaders lies in excavating the valuable in what is available.
  • I used a foil, which increased rather than diminished my efforts.
  • One of the dangers of guerrilla tactics and challenging power is the reality that those who stand to benefit may not stand with you.
  • They may not have been willing to fight with me at the time, but they admired my courage and ingenuity.
  • real and discernible differences exist between title and authority.
  • to rewrite the rules of power, never allow the position to limit your sphere of influence and control.
  • The other job of understanding the distinction between position and power is knowing which one you actually want.
  • just because someone has the office, do not assume he can do the work.
  • The opportunity for command may come in the form of overwork, sloughed onto your plate by a lazier boss.
  • the means to become a micro - boss shouldn't be ignored.
  • build skills, gain experience, and position oneself for the next big opening.
  • Another critical lesson in position versus power is not simply doing what you're hired to do ; the ones who move up also do what needs to be done, even if it's not their job and no one asks them to do
  • Power is directly tied to winning, and for those of us on the outside, the definition of winning must be adaptable to the circumstances.
  • Those who hold power have no interest in handing it over.
  • rely on two approaches : first, I distinguish my idea of a win from that of the ones in power, and second, I locate who can help me achieve my objectives, often through an activity known as power mapping.
  • identifying who had control or influence, understanding their relationships to others, and then targeting them to promote social change.
  • change the rules of engagement.
  • At its core, a power map identifies who is in charge of what and forces you to think about how you interact with each person.
  • Once I understand who is involved, I determine if they are willing to help me or if they'll be challenges to navigate.
  • Smart leaders internalize the limits of their own actions and search for counterparts who can help them move farther along.
  • The best ideas and the best policies are typically collaborative, and those that succeed are the product of a community.
  • The final essential element to changing the rules of engagement is to know what you believe and why you believe it.
  • If a leader doesn't have any hard - core internal holdings, she runs the risk of opportunism " making choices because others do so or because it's easy, not because the decision is correct.
  • I do have core beliefs, but I don't have an unshakable position on every issue. I accept that I may not know enough about a situation to render immediate judgment, which is why I attend meetings and read everything
  • My success tends to happen when I take on challenges that others refuse because the risk is too high and because it's hard to see the reward.
  • leading from a position of weakness is risky.
  • I reject the idea of work - life balance. It's worse than a myth. The careful binary of work or life entirely misses the point. The standards are stupid and arbitrary and make very little sense in universal application.
  • By prioritizing our interests, whatever they may be, we can distinguish between what we want and what we're told we should desire. And in the process, we find out what matters.
  • Invest early in the items that need to happen because they impact your ability to keep your options open.
  • Build up a reserve of goodwill and accomplishments, something we can dip into when the unforeseen happens.
  • The question to ask is whether their crisis will prevent you from achieving your goals " your firsts.
  • Untold amounts of lost time have been ceded to the urgent but not important, but you don't have to play.
  • DON'T DEAL WITH JERKS. The "jerks" label extends to flaky friends, the colleague with the constant emergencies, and the guy who always borrows but never lends. I've expanded the description to cover a host of people who are essentially unkind, those who place their needs above others and have little patience for the issues that don't involve them. "We don't deal with jerks also means looking in the mirror.
  • Reach out to the lowest - paid members of our teams to ask them about interactions with me. Am I short - tempered, distant, or terse ?
  • Being nice and suppressing our feelings can be taxing in its own way. We become numb to our own emotions, oblivious when they leak out, and start to damage relationships or even our health.
  • Good leaders are always at the ready but not always at the front.
  • I get a lot of things done because I do what I'm good at and let others shine in their roles.
  • Their prowess allows me to focus on the areas of my greatest capacities.
  • Doing a job another person can do, particularly better, is a waste of a precious resource.
  • Are you an essential element for success ? If so, go all in. If not, go away.
  • We are doomed to burnout if we fail to incorporate time for hobbies or just doing nothing.
  • When we buck against the conventional wisdom, we can be charged with being too disruptive or problematic. And with the absence of role models to show us the way, we are left with our own narrow experiences as guides.
  • To take power is to use the best of what resides within us for sketching a vision for the future, written large or small.
  • Power requires a conscious effort on our part to move our own lives to where we want them to be, because we've got to move against what historically has been defined as the way we should live our lives or inhabit this space.
  • Taking power demands self - analysis. You should regularly challenge yourself to do more, to be more, to examine your life and the world around you. Then endeavor to make modest improvements, knowing that, together, those incremental changes alter perceptions and then reality.
  • And let's not forget, privilege exists even within those who are encompassed by a minority identity.
  • There's a colloquialism I've embraced : let your haters be your motivators.