{"id":105031,"date":"2023-06-13T08:55:00","date_gmt":"2023-06-13T12:55:00","guid":{"rendered":"https:\/\/www.shortform.com\/blog\/?p=105031"},"modified":"2023-06-14T10:36:46","modified_gmt":"2023-06-14T14:36:46","slug":"the-road-less-stupid-book","status":"publish","type":"post","link":"https:\/\/www.shortform.com\/blog\/the-road-less-stupid-book\/","title":{"rendered":"The Road Less Stupid: Book Overview (Keith Cunningham)"},"content":{"rendered":"\n<p>Do you let pride cloud your judgment when it comes to running your business? Do you have goals but no plan for how to reach them?<\/p>\n\n\n\n<p>In <em>The Road Less Stupid<\/em>, Keith Cunningham says that to achieve <a href=\"https:\/\/www.shortform.com\/blog\/achieving-financial-success\/\">financial success<\/a>, you must avoid easy mistakes. He describes the top mistakes that you need to avoid and explains his methodology for thinking through <a href=\"https:\/\/www.shortform.com\/blog\/workplace-issues\/\">business issues<\/a>.<\/p>\n\n\n\n<p>Read below for a brief overview of <em>The Road Less Stupid<\/em>.<\/p>\n\n\n\n<!--more-->\n\n\n\n<h2 class=\"wp-block-heading\" id=\"h-the-road-less-stupid-by-keith-cunningham\"><strong><em>The Road Less Stupid<\/em> by Keith Cunningham<\/strong><\/h2>\n\n\n\n<p>The secret to financial success is to avoid making stupid mistakes, according to Keith Cunningham. And the key to making fewer stupid mistakes is to <a href=\"https:\/\/www.shortform.com\/blog\/be-kind-to-others\/\">think before you act<\/a>. If that sounds easy, it\u2019s easier said than done. In <a href=\"https:\/\/keystothevault.com\/the-road-less-stupid-advice-from-the-chairman-of-the-board\/\" target=\"_blank\" rel=\"noreferrer noopener\"><em>The Road Less Stupid<\/em><\/a> book, Cunningham discusses lessons that he learned the hard way, as well as business insights on a variety of issues, ranging from corporate culture to customer relations to risk assessment.\u00a0<\/p>\n\n\n\n<p>Cunningham is an entrepreneur, author, and speaker who runs a business school called <a href=\"https:\/\/keystothevault.com\/\" target=\"_blank\" rel=\"noreferrer noopener\">Keys to the Vault<\/a>.&nbsp;<\/p>\n\n\n\n<h3 class=\"wp-block-heading\" id=\"h-stupid-mistakes-that-smart-executives-make\"><strong>Stupid Mistakes That Smart Executives Make<\/strong><\/h3>\n\n\n\n<p>It\u2019s not practical to list every <a href=\"https:\/\/www.shortform.com\/blog\/how-to-avoid-silly-mistakes\/\">stupid mistake<\/a> that can or has been made in business, but some mistakes and misconceptions are common enough that Cunningham takes the time to discuss them particularly. Note that, as used by Cunningham, the word <strong>\u201cstupid\u201d refers specifically to things that you do or accept even though you are<\/strong><strong><em> smart enough to know better<\/em><\/strong><strong>. <\/strong>This contrasts with the way others sometimes use the term \u201cstupid\u201d to refer to a lack of intelligence.<\/p>\n\n\n\n<p>In this section, we\u2019ll examine these key mistakes so you\u2019ll be able to more easily spot and avoid them.&nbsp;<\/p>\n\n\n\n<h4 class=\"wp-block-heading\" id=\"h-letting-pride-cloud-your-judgment\"><strong>Letting Pride Cloud Your Judgment<\/strong><\/h4>\n\n\n\n<p>According to Cunningham, letting your emotions influence your business decisions will almost always result in stupid mistakes, which, in turn, will result in financial losses. <strong>One of the most dangerous emotions of all is pride<\/strong> because it can cause you to ignore risks or expect unrealistically easy profits<strong>.<\/strong>&nbsp;<\/p>\n\n\n\n<p>He warns that having too much pride in your past successes can inflate <a href=\"https:\/\/www.shortform.com\/blog\/your-ego\/\">your ego<\/a> and give you unfounded confidence in the future success of your projects. In recounting his own greatest financial losses, Cunningham observes that one of the few good things about failing badly is that it humbles you. One humbling failure can help you view future projects more objectively because it takes humility to learn new things and assess your own ideas honestly, both of which are important for anyone directing a business.<\/p>\n\n\n\n<p>But even if you\u2019ve been humbled by failure, he says it\u2019s helpful to have someone else who can review your proposals without getting emotionally involved. This second check helps keep your pride in check and prevents a lot of stupid mistakes. Many businesses have a board of directors for this purpose.<\/p>\n\n\n\n<h4 class=\"wp-block-heading\"><strong>Building What You Want Instead of What Your Customers Want<\/strong><\/h4>\n\n\n\n<p>Cunningham also argues that <strong><a href=\"https:\/\/www.shortform.com\/blog\/benefits-of-doing-what-you-love\/\">doing what you love<\/a> and expecting to somehow make money on it is fundamentally a stupid idea<\/strong>. If you want to make money, you need to find out what <em>your customers <\/em>love (and are willing and able to pay for) and deliver it efficiently enough to make a profit.&nbsp;<\/p>\n\n\n\n<p>For that matter, if you want to make <em>more<\/em> money or grow your business, Cunningham says you\u2019re usually better off researching why people who know about your product <em>aren\u2019t<\/em> buying it and addressing their concerns, rather than expanding your advertising to reach more people. <strong>If your product is making a bad impression, it\u2019s stupid to expand your advertising<\/strong>, because then it will just make a bad impression on more people.<\/p>\n\n\n\n<p>However, if there\u2019s a grain of truth in the philosophy of doing what you love, it\u2019s that you have to start with an understanding of your own resources and capabilities (which probably align with <a href=\"https:\/\/www.shortform.com\/blog\/what-are-you-curious-about\/\">your interests<\/a>) so you can make plans that you can realistically execute as you consider ways to win new or repeat customers.&nbsp;As Cunningham explains, starting with a realistic understanding of what you can do now helps you avoid another common business misconception: the idea that you should first identify your goals or desired end-state, and then plan <a href=\"https:\/\/www.shortform.com\/blog\/how-to-achieve\/\">how to achieve<\/a> them. This philosophy implicitly assumes that you have the resources to <em>execute<\/em> any long-term vision that you can <em>plan<\/em>. And since you don\u2019t have infinite resources, that\u2019s a stupid assumption.<\/p>\n\n\n\n<h4 class=\"wp-block-heading\"><strong>Confusing Goals With Plans<\/strong><\/h4>\n\n\n\n<p>According to Cunnigham, another stupid mistake that frequently tempts executives is to establish a goal or vision for improving the company but fail to establish a detailed plan for achieving it. <strong>Just thinking about a desired end state doesn\u2019t help you get there<\/strong>, no matter how much you want to. To reach it, you need to identify what obstacles stand between you and your goal (you\u2019d already be there if nothing was <a href=\"https:\/\/www.shortform.com\/blog\/whats-holding-you-back\/\">holding you back<\/a>) and figure out exactly what you need to do to overcome those obstacles.&nbsp;<\/p>\n\n\n\n<p>Cunningham further explains that, while a detailed plan enables you to progress toward your goals, letting your plans become sacred is another stupid mistake. The value of a detailed plan is that it\u2019s actionable (unlike a goal), and it gives you a standard against which to <a href=\"https:\/\/www.shortform.com\/blog\/track-your-progress\/\">track your progress<\/a> so you\u2019ll know when you begin to deviate from it, as you inevitably will at some point. Deviations aren\u2019t always a bad thing\u2014sometimes you may discover opportunities along the way that are better than your original goal. But it\u2019s important to know when you start to deviate so you can reassess the situation and update your plans as needed.<\/p>\n\n\n\n<h4 class=\"wp-block-heading\"><strong>Misunderstanding Corporate Culture<\/strong><\/h4>\n\n\n\n<p>One stupid mistake that, according to Cunningham, can have a devastating effect on productivity is misunderstanding the concept of corporate culture. Specifically, thinking that you can create a culture of high performance by creating a few unique job perks is stupid.&nbsp;<\/p>\n\n\n\n<p>He explains that corporate culture is the code of conduct that dictates how people in the company act by delineating the difference between acceptable and unacceptable behavior. <strong>Establishing and maintaining a positive, high-performance culture requires a constant dialogue about what\u2019s acceptable and not<\/strong>. And if you fail to enforce the rules, that will undermine the culture.<\/p>\n\n\n\n<p>Disciplinary actions <em>can<\/em> be effective for correcting unacceptable employee behavior, but they can also create a <a href=\"https:\/\/www.shortform.com\/blog\/culture-of-fear-in-the-workplace\/\">culture of fear<\/a>, which produces less-than-ideal performance. Cunningham observes that every employee <em>wants<\/em> to succeed. So before you resort to firing or otherwise disciplining an employee who isn\u2019t meeting your expectations, he recommends assessing whether she understands your expectations and whether she has the skills and resources to meet them. If not, you may be able to clarify your expectations or enable her to meet them by providing the training or support she needs.<\/p>\n\n\n\n<h3 class=\"wp-block-heading\"><strong>Avoid Mistakes by Taking Time to Thin<\/strong>k<\/h3>\n\n\n\n<p>Cunningham\u2019s solution to the problem of making stupid mistakes is to set aside blocks of time for deep thinking that force you to confront issues and answer questions you might otherwise have failed to consider. Schedule thinking sessions at least twice a week and ideally every day.&nbsp;<\/p>\n\n\n\n<p>Each <a href=\"https:\/\/www.shortform.com\/blog\/how-to-avoid-mistakes-at-work-2\/\">thinking session<\/a> is one hour long: You spend the first 45 minutes pondering questions or problems and jotting down possible answers or solutions. Then you spend the final 15 minutes evaluating the ideas you came up with and documenting any that are good enough or important enough to warrant following up on\u2014whether in a future thinking session or as actionable business directives.<\/p>\n\n\n\n<p>Cunningham stresses the importance of minimizing distractions during your thinking sessions so you can focus deeply on questions and issues. In addition to blocking off the time in your schedule so that you won\u2019t be interrupted, he recommends setting aside a specific place for thinking, such as a separate desk or a chair in a corner of your office where your computer screen and other reminders of pending tasks will be out of sight. He even has a separate pen and notebook that he uses only for documenting questions and ideas during thinking sessions.<\/p>\n\n\n\n<h4 class=\"wp-block-heading\"><strong>What to Think About<\/strong><\/h4>\n\n\n\n<p>Cunningham advises you to <strong>start each thinking session with at least one question that you want to ponder but no more than three<\/strong> so you can focus deeply on them and get past the obvious, superficial answers to more original, insightful answers. He observes, though, that once you start thinking about a question, it often spawns other questions. Also, most important questions take more than one session to really think through, so don\u2019t worry if you don\u2019t answer all your questions in a given session.<\/p>\n\n\n\n<p>What specific issues should you ponder in your thinking sessions? Aside from contemplating whether you\u2019re making any of the mistakes that he calls out specifically, Cunningham discusses a number of general questions you\u2019ll probably need to ask from time to time, so consider starting your thinking session with one or more of the following:<\/p>\n\n\n\n<p><strong>1) What questions or issues<\/strong> are most important for you to consider right now? Cunningham urges you to periodically ask yourself whether you\u2019re <a href=\"https:\/\/www.shortform.com\/blog\/how-to-ask-the-right-questions\/\">asking the right questions<\/a>. He notes that when you can\u2019t seem to come up with a good answer to a question or problem, it\u2019s often because you\u2019re asking the wrong question.<\/p>\n\n\n\n<p><strong>2) What are the real problems <\/strong>you need to solve? Are the problems you\u2019re currently trying to solve the actual root problems or just symptoms of an underlying problem? You might spend a thinking session listing possible causes for a given problem, or listing actions and events and asking yourself whether the problem would go away if a given event happened or stopped happening.&nbsp;<\/p>\n\n\n\n<p><strong>3) What can you do to solve a certain problem?<\/strong> Once you figure out what the <em>real<\/em> problem is, ask yourself what you (and your organization) can do to overcome it. We\u2019ve discussed the difference between goals and plans. Solving the problem is your goal, now you need to plan your solution. As you make your plan, ask yourself what you need to change about your corporate focus or strategy, as well as how you\u2019ll need to reallocate resources and rethink your metrics to support the change of focus.<\/p>\n\n\n\n<p><strong>4) What are your assumptions?<\/strong> As you consider any change or new venture, Cunningham advises you to think about the assumptions you\u2019re making in assessing its potential. Consider whether the assumptions are reasonable and how you could validate them. Unfounded assumptions can lead to stupid mistakes, especially if you don\u2019t realize you\u2019re making the assumption until it proves to be false. You\u2019ll want to consider the risk of each assumption turning out to be wrong.&nbsp;<\/p>\n\n\n\n<p><strong>5) What are the <a href=\"https:\/\/www.shortform.com\/blog\/unexpected-consequences\/\">unintended consequences<\/a>? <\/strong>Cunningham observes that even if none of the risks that could hinder the success of your project are realized, the project itself could have unintended consequences that pose another kind of risk. For example, maybe you roll out a new product with special safety features, and people trust the new features so much that they take bigger risks when using it, such that the new safety features actually result in an<em> increase<\/em> in injuries.<\/p>\n","protected":false},"excerpt":{"rendered":"<p>Do you let pride cloud your judgment when it comes to running your business? Do you have goals but no plan for how to reach them? In The Road Less Stupid, Keith Cunningham says that to achieve financial success, you must avoid easy mistakes. He describes the top mistakes that you need to avoid and explains his methodology for thinking through business issues. Read below for a brief overview of The Road Less Stupid.<\/p>\n","protected":false},"author":14,"featured_media":71103,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_jetpack_memberships_contains_paid_content":false,"footnotes":""},"categories":[40,45,14],"tags":[1058],"class_list":["post-105031","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-books","category-business","category-management","tag-the-road-less-stupid","","tg-column-two"],"yoast_head":"<!-- This site is optimized with the Yoast SEO Premium plugin v24.3 (Yoast SEO v24.3) - https:\/\/yoast.com\/wordpress\/plugins\/seo\/ -->\n<title>The Road Less Stupid: Book Overview (Keith Cunningham) - Shortform Books<\/title>\n<meta name=\"description\" content=\"Your silly mistakes are holding you back from financial success. 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