Few activities prompt vicious self-recriminations as readily as reading about the myriad successes of some hot young entrepreneur who’s made his first million by the age of 25 and remains happy, healthy and content as he trots the globe with a hottie draped on one arm and the boarding pass to his private jet clutched by the other. For an oh-so-recent example: Inc. Magazine‘s November 2011 cover profile of Jared Heyman, the 33-year-old CEO of Infosurv who left for a year to amble around the world while others ran his business (Inc. helpfully provided several photos of Heyman’s chiseled shirtless torso, just to rub salt in the wound). Meanwhile, the 30- or 40-somethings among us, who sometimes worry whether we’ll be able to pay the rent at the end of the month, read these modern-day hagiographies and say: There, but for the indifference of God, should have gone I. 

At some point during our childhood, each of us wanted to be an astronaut when we grew up. The question, though, is why so few land among the stars while the rest of us believe we’re cruelly trapped by the iron bands of gravity. Very few people believe themselves to be incompetent dolts who have no real future. We all have our strengths and weaknesses. We have our dreams, and fundamentally we all believe ourselves capable of Achieving Great Things.

If we concede that everyone is equally capable of excellence, then the question of why some people fail to achieve takes a special significance. Why do people fail at life? What root causes of systemic unhappiness contribute to a person’s grudging choice to sit on the sidelines while wishing he competed on the field? Can we avoid the mistakes of others?

Having observed and counseled many people over the years — aspiring business owners, college students wondering what to do with their lives, prison inmates, the hospital-bound terminally ill — I think I have a stab at an answer or 13. 

1. You don’t know what you want. I remain astonished at how many people can’t articulate a clear sense of who they are and what their life’s mission is. Reminds me of some of the women I dated a few years ago — they knew they wanted a man, but they didn’t really know what kind of man (or whether the kind they thought they wanted actually existed in the real world). Hence, they bounced from bad date to bad date, never understanding why they couldn’t find Mr. Right. Swipe a page from my playbook: Take the time to think through who you want to be on the morning of your 70th birthday or what you want your obituary to look like.  If you do it right, the process should take weeks or months, not a few minutes with a notepad. Ask yourself some hard questions. What’s important to you? What things do you want to accomplish? Write them down. Plan how you intended to achieve them. You may find that your ideal life and your current life are radically out of sync (as was the problem for me). If so, you have ample opportunity to engage in a mid-course correction. In any case, clearly identifying your life’s purpose and mission provides you with a valuable yardstick with which to gauge the suitability of any future major life choice. Does it cohere? Doesn’t it? Does your life plan need revision? Consider it a work in progress. Just don’t live the unexamined life. I’ve seen too many people on their deathbeds who spoke only of what they regretted, instead of taking comfort in what they had achieved. The tragedy of it tears at the soul.
2. Your thinking is too tactical. Some people are organized with Teutonic efficiency. They have checklists galore, and hierarchies of sticky notes plastering their workspace. They know what they need to do, and have their life scheduled months in advance. But they’re too busy with execution to put all their tasks into a big-picture framework. They do, without thinking about why they do; these are the folks who cannot see the forest for the trees. If you find yourself drowning in tasks, put them aside. Classify them, and figure out whether they’re actually worth your time. When necessary, say no. Declining unnecessary work is incredibly liberating.
3. Your thinking is too strategic. Of course, other people’s hearts never leave the Left Bank. They always think about the big picture but they never concentrate on the various steps necessary to bring that big picture into focus. These are the folks who are so fascinated by the forest that they keep running into the trees. The best way to drill to the tactical when you’re inclined to think big is to start with a cloud diagram. Put your dreams in the middle. Put hubs and spokes out that describe all the things necessary to accomplishing those dreams. Connect them with arrows, as appropriate. The process is called “mind mapping” and its great for helping creative thinkers become organized at a more granular level. Use the mind map as a starting point for developing task lists or other planning tools.
4. You’re a jack of all trades or a master of one. People love polymaths, but the trouble with them is that they’re a mile wide and an inch deep; they are great at drawing connections among disciplines but their perspectives remain too superficial for serious application. People also love content experts, but these wise men often are so consumed by a narrow area of study that they cannot link ideas from different disciplines coherently into a complex picture. People become specialists or generalists in response to different pressures — usually career-focused. Better, though, to  be a jack of few trades and a master of some. Know a little bit about a lot, but cultivate sufficient depth in several areas. My personal recommendation is to know a lot about philosophy (logic, ethics, epistemology) and communications theory, and then become familiar at more than just the surface level in disciplines related to your area of interest. For example, I’m a certified scuba diver. I can talk with some “depth” (pun intended) about diving, pontificating with a degree of mastery, but I’m not a dive instructor; I’m not a genuine expert in the subject. But that’s OK. I know enough about diving to know the broad outline of the subject, which also helps me to understand and appreciate what I know that I don’t know.
5. You decline to accept 100 percent responsibility for your situation. A common refrain from the prison inmates I’ve counseled: Someone else was responsible for their incarceration. I volunteered in a now-closed Michigan prison that had a high concentration of sex offenders. If I had a nickel for every time a middle-aged man blamed his girlfriend’s teenaged daughter for putting the moves on him first, I could afford to re-open the prison singlehandedly. Funny thing is, the scenarios they described often happened just as they explained; never underestimate the extent to which teenage girls in certain socioeconomic conditions will compete with their mothers — even if it means seducing her mother’s man. Yet the men were hardly victims; sexual activity requires the active participation of (at least) two people. Regardless of which side of the bars you happen to fall, the temptation to blame circumstances for a failure, instead of fully owning your stake in it, precludes learning from one’s mistakes. It also sets up a victim mentality that inhibits reasonable risk-taking. A good strategy for any failure is to examine what happened and what you did that contributed to the outcome. Own that stake, even if you aren’t solely responsible. Learn from it. Don’t pass the buck.
6. You are paralyzed by analysis. One of my life goals is to complete a through-hike of one of the major trails in the United States — the Pacific Crest Trail. This 2,600-mile excursion takes five or six months to complete, starting at the Mexican border near San Diego and ending at Manning, British Columbia. As part of my research into this bucket-list goal, I’ve joined a few email discussion groups. One thing that becomes quickly apparent is that there are a lot of people who, year after year after year, say that they’ll try it “next year.” Many of them explain their delays in terms of logistics: They need to research gear more carefully, or try a day hike or two, or sell the condo, or whatever. Truth is, it’s not all that difficult to hit the trail, but the planning process becomes a surrogate for actually performing the hike. These wayward souls have gotten so lost in their check sheets and outlines that they never actually manage to step foot on the trail. At some point, you need to move from planning to execution.
7. You don’t perform adequate due diligence. I love Pat and Ali, the infamous “Bumfuzzle” duo. Almost a decade ago, they spontaneously quit their jobs in Chicago to sail around the world. They sold everything, bought a catamaran, and set out — with no real sailing experience at all. They blogged about their adventures, gaining the respect of folks like me and the chiding of armchair sailors who have spent half a lifetime “getting ready” to sail but kept finding reasons to not experience the open water. I loved their blog; their sundry misadventures delighted me and the fact they stayed safe and had fun warmed my spirits. Pat and Ali were lucky, though — they did something dangerous, with almost no research, and ended up being successful. Most people who don’t dive deeply enough into the background and logistics of their ideas find themselves stymied by avoidable errors. Rule of thumb, courtesy of my late grandfather: Anything worth doing is worth doing right. That includes appropriate study.
8. You don’t keep abreast of new trends. My friend Duane was a cutting-edge game designer back when the TRS-80 was hot new technology. Then he joined the Army, and after a successful career as an officer, he tried his hand at programming again after he left the service. Result? He struggled. Because he wasn’t able to keep up with changing technology (a result of his overseas deployments), he missed several formative generations of software design. Most people, though, don’t have Duane’s special problem; they refuse to keep abreast of new trends not because they’re stationed on the DMZ but because they think they’ve mastered the subject and therefore no longer need to study it. Then, when time passes, the lessons of the past become less relevant — as do the skills and perspectives of the person whose arrogance stopped him from being a lifelong learner. Tip: Read relevant magazines or RSS feeds. Small time investment, big reward.
9. You’re horrible at time management. Life requires project management skills. Silly as it sounds, the best way to ensure progress on your goals is to treat your whole life like a program and use a consistent PM methodology to keep it on track. Disorganization saps the vitality out of the best-laid plans. To avoid failing because time management presents a challenge, use products like Microsoft Project or Open Workbench to set up a task/dependency list and look at dates on a Gantt chart. File “status reports” in the form of a weekly personal blog or diary. Identify scopes and exclusions and make sure that individual goals follow the SMARTER approach — specific, measurable, achievable, relevant, time-limited, ethical and rewarding. Plan for the long term, chunk major goals into smaller tasks and schedule deliverables in reasonable fashion.
10. You have no coherent social strategy. Success is almost never a solitary affair. We need networks of friends, funders, partners and lovers to shore up our weakness and help us to better leverage our strengths. Yet I remain astonished at how little attention most people pay to the size and quality of their personal network. Spend time on like-minded discussion forums, participate in LinkedIn/MeetUp groups, join a business networking organization. Do something to bring allies into your struggle for success, for trying to go it alone is usually a great way to fail. Note, however, that “social strategy” means “people you know in the real world.” Having 100,000 Twitter followers you’ve never heard of means nothing if you don’t actually have recourse to human beings who will help you directly, and who will accept your help in return.
11. You’re too comfortable to push your limits. The sweet siren of comfort: It’s better to relax today than to put in the hard work to make tomorrow better. How many of us with grand plans for the next better mousetrap never follow through because we rationalize why we need to protect the not-very-fulfilling day job we already have? How often do we say that our current lot is good enough so that we never risk it on a high-risk, high-reward pursuit that could put today’s comfort on the line? Comfort and risk aversion represent the Scylla and Charybdis on the map of success: You need to chart a course between them to make it to the other side.
12. You’re a poster child for sloth. A dear friend of mine has the potential to be a nationally recognized film reviewer; he know the industry, he writes with a sharp-witted flair and he genuinely loves the “best of the worst.” But he’ll never actually try to break into the market. Too much work. Good ideas mean little if you’re unwilling to invest the blood, sweat, toil and tears necessary to deliver on a major life goal. If you find yourself with a laundry list of goals, but you go home after punching the clock and tinker on the Web or watch TV or otherwise do absolutely nothing as a routine part of your work week, you’re in the clutches of Sloth. Until you slay that demon, you won’t make it except by accident.
13. You’re too agreeable to succeed. Gillikinism #47: “Nice people finish mid-pack.”  Success in a competitive environment requires aggression. It requires you to stand up for yourself, to fight for your dreams, to protect your investments of time and money, to never settle for half the loaf, and to beat your peers into respectful submission. Nice guys don’t finish last, but they don’t finish first. Grow a spine and be willing to fail over and over and over until you finally succeed. Be Steve Jobs, without the furniture-throwing temper tantrums. Embrace every failure as learning one more way of how not to do it.

Success is difficult. Success of the kind that gets your shirtless photo on the cover of Inc. Magazine is damned difficult. The funny thing, though — it’s possible. The tools of victory are always within our grasp. The challenge is to identify the snares we’ve set for ourselves and then use those tools to disarm them, one by one, until we realize that the real reason you’re not successful is — you.

After you internalize that insight, and adjust your attitudes and practices accordingly, your success is almost guaranteed.

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