Can you imagine starting a company without ambition? Impossible. Whatever your vehicle, ambition is the fuel; it’s what you dream about and what gets you up before the alarm every morning. Ambition takes you places.

Except when it doesn’t.

Conventional management theory construes ambition as goal-oriented: You’re aiming for objective X – excellence, recognition, profits, power, changing the world. The common assumption is that satisfying ambition is directly tied to reaching your goal. All you really need to focus on is how – the metrics and strategies to smart, bold, effective business-building.

But goal-attainment is only one piece of the puzzle.

Ambitions are generated by lots of other psychological factors – not just the fire to aim and go. What they’re actually made of strongly determines the route you’ll ultimately take and how you feel on the way.

From the outside, it might appear that all ambitious people are moving forward in pursuit of their respective brass rings, be it an expansion or acquisition, fulfillment and contentment, or making meaningful contributions to marketplaces and society (making a good living doesn’t hurt either).

Under the surface, however, not everybody’s traveling in the same direction. In fact, some people are going backwards.

Some ambitions are propelled by guilt, fear, hate, an intense need to seem impressive or not to be a failure. What else? To redress wrongs, overcome deprivations, or disprove, destroy, or defend. That’s a short list. For those in this group, chances are, no matter how many candles are burned at both ends, even if they reach some version of success, real, sustainable satisfaction is gonna be tough.

Why? One reason is that the objective goal isn’t the actual goal. The engine of ambition is powered by those underpinning imperatives and obstacles, which remain untouched and unsatisfied by the actual achievements.

Consider Joel M., 40, founder, owner, and chief visionary of an East Coast multimedia production company (I’ve changed a few details to disguise his identity). After years of dreaming, sweating, and struggling, Joel is now standing with both feet planted in paradise. Armed with talent, charisma, a stellar track record, and a fluorescent business plan, he landed ample VC funding with nominal startup or operating restrictions. Joel shot out of the gate with economic, creative, and administrative freedom. He’s working out of a dream shop with state-of-the-art equipment, a gonzo sweet budget for marketing, development, and Slurpee-sized Lattes. Be careful what you wish for; you might get it. He’s miserable. And it’s making him f@*# up. Not cool.

What’s going on? Joel started dreaming this dream long ago. Its superstructure developed over the years and got polished to further his professional pursuits. But it’s a gleaming Santiago Calatrava tower with a decrepit old barn for a lobby. His early life involved parents who were fundamentally uninvolved and disinterested in him. He grew up longing for a magical switcheroo: his real life for one where people truly cared and he got what he asked for.

It looks like his wish was granted, sort of, but it’s definitely not the solution he hoped it’d be. Sitting in his Hermann Miller chair in his super-duper studio, he’s still holding the same bag of rocks.

What to do? One of the first steps when I’m engaged as an advisor to any entrepreneur, executive, or business owner in this situation, is to start parsing the operational factors from the psychological ones. Each impacts the other. Are you unhappy because the ingredients for happiness are objectively absent or deficient, i.e. you’re disenchanted with the business you’ve built or the people you work with? Are there are organizational problems, such as staffing, marketing, production issues, cash flow difficulties, or other mechanical hiccups? Or is it that there’s something inside you causing an obstruction to feeling fulfilled?

For Joel, this means helping him understand where his dissatisfaction is actually coming from so he can start to value what he has, not what he doesn’t. The lament for his unfortunate childhood may ache into old age. But it’d be tragedy compounded to wreck his new business on account of it.

You’re not going to find a global formula for success, and emulating the 7 habits of successful people will probably only guarantee that you can succeed in emulating seven of their habits.

What you can do is identify and unhook your personal psychological Bungee cords that may be thwarting your ambitions.

Expectations are the fulcrum of business. Customers and clients will come or go on their expectation that you will, or won’t, satisfy certain requirements. Likewise, your expectations of your staff and yourself can propel you forward in common purpose or drive you apart in dissatisfaction.

Expectations are there to be met, dashed, or exceeded.

But what are they? Expectations are outcomes considered most likely to happen. They can be based on experience or they can be speculative – meaning the desired outcome rides on an unsubstantiated prediction or not necessarily realistic hope. As in, I like that company’s logo. I’m sure they make superior widgets. I’ll buy some. Or, this strategy tanked the last seven times we tried it, but I’m confident it’ll fly this time. Let’s go all-in.

While there’s no shortage of simple-minded articles intended to help business owners develop so-called best practices for managing customer and employee expectations, it’s really not so simple. Actually, expectations are more like theSupreme Court’s definition of pornography – hard to define but you know it when you see it. They’re personal.

I’ve been thinking a lot about expectations after I got this email from a reader who was responding to my last BNET post, “What’s Really Holding You Back From Getting Things Done?” (it has been edited for clarity):

I started my online business 4 years back … After our initial launch, the plan was to create more websites dedicated to other services in this space. Since then I’ve just been stuck with the one website and one relatively recent launch. I keep getting stuck with issues, feature requests, etc. How a couple of years went by like that, I’m not sure.

I guess part of the problem was that I just didn’t know how to hire for and delegate the work I was doing myself. I’ve tried delegating and I’m not very successful at it. I just want to do a lot of things myself because I don’t trust my team will do it well (they’ve made big mistakes in the past) and I just like to be in total control. This trait of mine unfortunately has led me into a situation where I’ve landed myself with such a huge to-do list that I don’t really end up completing. Plus, I’ve been so involved in solving issues as they come up that I haven’t really been supervising the team of people under me enough. Things just don’t seem to be progressing anymore. What should I do?

A cornerstone of my work as a business adviser is first understanding as much as possible about a situation and its causes before prescribing remedies. So without knowing a lot more, I can’t definitively answer the question of what this guy should do.

But this is what I hear at the surface: inadequate start-up planning and meager development strategy, indecisive leadership – including poor staffing choices, difficulties delegating, and ineffective management – and flat-footedness in identifying and addressing the myriad hurdles and set-backs most new businesses are bound to face in some form or another.

All important to correct. But they’re by-products. The real culprit: everything encompassed by what he calls “this trait of mine” – the underlying issues causing his self-defeating decision making, mis-calibrated expectations of what’s probable, and paralysis to effect necessary course changes.

I’d recommend a two-pronged approach to jump-starting this stalled venture.

1. The first entails making a host of smart and solid business choices:
   • Staff: Cut the chaff and bring on some wheat.
   • Leadership: Consider engaging a sharp, seasoned co-helmsman.
   • Systems and Operations: Get competent assistance to analyze the administrative and procedural back-log and implement appropriately prioritized solutions.
2. The second has to examine why these problems arose and then were left to fester:
   • Understand your strengths and weaknesses.
   • Enlist help for both.
   • Scale and align your expectations with your actual capabilities and circumstances, not the ones you wish you had.

Remember that expectations are about future events. And the key to advantageously managing expectations is correctly interpreting patterns from previous events.

So don’t just look ahead; look back too.

Business doesn’t get done if you can’t get things done. Simple as that. Every business owner knows that good time management is a corner-stone of profit and productivity. And that ineffective or inefficient use of time accounts for a substantial drain

Sure, your schedule’s already tighter than a NASA mission, and your to-do list is longer than the Health Care Bill. But still, there are only 24 hours in a day. Do you suffer from GMTD (general multi-taskcrinating disorder), meaning you can’t do everything because you’re trying to do everything?

There’s no shortage of apparently helpful resources to boost your time management IQ: blog posts, coaching advice, productivity experts, even tips from the Ãœber-guru of Getting Things Done.

But the most popular strategies espoused by the experts above mainly look at the first three inches of why productivity falls into a gully – too many distractions and interruptions, poor prioritizing, disorganized to-do lists, tech glitches. The fixes and work-arounds they typically offer are just as superficial.

Beyond all of those surface issues, there is much more to the problems of chronic procrastination, edge-of-the-minute task completion, and behind-the-8-ball management. My advice: Look deeper to learn what’s really holding you back, and how to get – and keep – you and your business ticking.

Start by realizing that it’s not about time; it’s about your relationship to the goal. What do I mean? Consider these feet-dragging business owners (I’ve disguised some identifying details here):

Theo: He recently brought a thoroughbred creative director into his design firm. His new superstar is attracting buzz and blue-chip projects. Now, to leverage this and really take his business to the next level he needs to streamline operations and show a few duds to the door. But he keeps putting it off.

James: Following a dazzling attention-grabbing product launch, a new client he’d been courting for months presented him with a game-changing opportunity. To make this fly, James has to put himself and his staff in hyper gear. He knows exactly what needs to be done. But he’s deferring all the preliminary activities.

These successful, high-performing CEOs can manage their inboxes, wrangle their to-do lists, and say “no” to low-priority tasks until they’re as sleek and efficient as Michael Phelps in the 200m butterfly. But here’s why none of that will unhook them from their critical sticking points.

Theo is ambivalent about growing his business. He’ll tell you he’s ambitious and his success to-date is proof of that. But now that he’s actually positioned to kick things up a notch or three, part of him isn’t so sure he’s ready-or willing-to run a hot-shot shop handling high-profile work.

The Fix: Theo’s business issues are playing out in staffing and time management but to run his business better, he needs to first resolve his conflict about where he wants to go.

James is by every objective measure an admired and successful 44-year-old businessman with plenty of entrepreneurial drive. He knows how to plan and execute. Being the best is what gets him up in the morning. But privately, he sees himself as a teenage prodigy with a lifetime of potential still to realize. He’s unable to relinquish the feeling that his best is yet to come. So, however irrationally, he wears gravity boots, struggling harder than necessary to reach every new brass ring, unknowingly holding himself back in the past.

The Fix: James’ apprehension feels real enough. But it’s an old impediment (which surfaces at crux moments) that needs to be quarantined and resolved separately from business. In my experience, problems with time management are rarely only about the management of time. For many business leaders, procrastination and other similar struggles are usually a symptom – visible evidence, as with Theo and James, of some personal friction or restriction about moving forward.

Bottom line: Getting things done is a completely learnable and improvable set of skills. But to really optimize your use of time, don’t just grease the clock. First understand why it’s off.

Entrepreneurs, what are you putting off? Email me your situation (here’s my contact page) and I’ll analyze it in a future blog post.

Alexander Stein, Ph.D., business psychoanalyst, is a principal in the Boswell Group, a consulting firm focusing on the psychology of business.

What are the key factors that make or break your business? Your product or service? Your customers? Capital? Just plain luck?

Sure, those are all important. But I’d argue that ultimately it comes down to people, and more specifically: you. As chief executive, you impact every aspect of your business. Even when you delegate, your personality and decisions influence everything. It stands to reason that leaders who are psychologically in tune – meaning resilient, agile, and aware – are not only more effective, they also bring an unmatchable competitive advantage to their businesses.

How can you make that happen?

Many leaders – even those who run businesses with people-centric cultures – tend to prefer a straight-ahead, hit-the-ground-running, just-make-it-go approach to managing people. The alternative I recommend is an inside-out – rather than outside-in – view of managing people. When an employee makes a mistake or a bad decision, your first question should be “Why did he do that?” not “What can we do about it?” In the long run, this more psychologically savvy management tactic pays dividends. If you want to motivate someone, you better understand first what motivates her.

To me, this is common sense, but, of course not everyone in the business world agrees. A recent article in The Economist would have managers believe that trying to understand a worker’s psychology amounts to meddling. Worried about an employee’s emotional state or stress level? Careful, that may very well cross a privacy boundary! In fact, the article refers to the business world’s “new-found interest in promoting mental health” as if that were a bad thing. It questions the assumption that “promoting psychological wellness is as axiomatically good as encouraging the physical sort,” and worries that a “mental-wellness movement” will inevitably attract “charlatans and snake-oil salesmen.”

I can’t post the word that captures my true opinion of all that; “bunk” will have to do. Think of the issue this way: If your copy machine is broken, you fix it; if your delivery system is gunked, you grease it; if your shop is dark, you light it. Why treat the human factor less responsibly?\

Obviously, understanding and changing people is more complex than copiers and light bulbs. But the same principles hold: If, say, your sales team’s performance needs your attention, you attend to it; and the right procedure follows a good diagnosis.

And by the way, dysfunction shouldn’t be your first clue to pay attention. Like world-class athletes, top business leaders improve on excellence by understanding what already works well. The more you know about yourself and the underlying forces that push and pull you, the better equipped you’ll be to make even better decisions going forward.

What to Do: Strengthening your business by investing in “psychological capital,” as I call it, doesn’t happen overnight. But here are two key pointers to get you started, culled from my experience advising entrepreneurs and senior executives navigating complex circumstances and looking to refine their leadership capabilities:

1. Understand that we all naturally assert the vexing tendency to try to keep things the same, notwithstanding good intentions and recognized imperatives to make things different. Have you ever resolved to lose weight, quit smoking, be more patient, or otherwise try to change yourself? How did it work out? My point exactly. So long as this potent streak of irrationality is left unchecked, your magnificently designed and deployed blueprints for business success are in constant danger of becoming irrelevant.

First step: Identify the issue – say, become a better listener, feel more confident at board meetings, get your SVP to micro-manage less, understand why morale is low.

Next: Start thinking about what the issue is made of, not how to change it. Talk about your ideas with a spouse or trusted colleague, confidante, or consultant.

And remember, dismantling and reconfiguring entrenched systems requires time, thoughtful attention, and heavy lifting.

2. Change isn’t about finding easily opened doors. Whatever your desired outcome, what’s most crucial to geting there is identifying and unraveling the tangle of ingredients, understanding how and why they got there, and then putting something new in motion.

Consider the co-founders of a music production and distribution business. The partners, Frank and Darryl, thought they were on the same page about all the important things. Business was good, and they were good friends. But when I first met them, I found two guys at loggerheads over nearly every decision. Already behind schedule on several high-value projects, they felt pressured and wanted me to help them resolve things yesterday.

The deadlines were real enough. But the pressure was synthetic; they’d deferred addressing their conflict until it was nearly too late. Now they were making instant resolution my responsibility.

Here’s what we did: With me and then together, they aired out their simmering frustrations and resentments so that eventually, the temperature lowered enough for them to actually move ahead on time.

The job wasn’t done once I’d helped them achieve on-time completion. That was only a temporary flight back into the good working stasis they already knew.

Getting Frank and Darryl’s partnership, and their business, truly solid required navigating through the substance of their discord, learning why it was there, why things had finally gone south after years of apparent harmony, and helping them know how to unstick themselves in the future.

We’ve all been there: the crossroads between one decision and another: Go or stay? Now or later? This or that? What’s right? Sometimes, the answer’s easy – the choice seems obvious and you just know what to do; sometimes, it’s not. And sometimes you make decisions you don’t even realize you’re making.

So what goes into a high-stakes decision? And how can you improve your stats on making advantageous choices?

Being a consistently above-average decider is about more than devising a roster of binary options – do vs. don’t, this vs. that, now vs. then, here vs. there – and then pulling each trigger with optimal timing such that intention and outcome are aligned. All important, to be sure. But it’s only what you’re deciding, the external metrics of goals and actions.

The DNA of how and why you make decisions is different. It’s fundamentally about who you are, and what happens to you in x, y, or z circumstance.

Consider Ed Clooney (not his real name), 55, who heads a 60-employee East Coast advertising firm. In our first meeting, Ed fired off criticisms of his senior managers – middling project execution, waffling on client matters, mishandling staff and operations issues, squabbling between themselves. My task: “Figure out why my boys are off track and get them back on it,” he implored.

I’ve heard this from the corner office before; the story is inevitably more complicated. Far from being ineffectual, I eventually learned that Ed’s management team was holstering its collective skills and talents in response to Ed. Though he was completely unaware of it, turned out Ed used a bait and switch: He thought he was encouraging Alpha decisiveness – and so felt justified in his annoyance at his lieutenants’ failures to follow his leadership. But what he unwittingly communicated was that he didn’t really want anybody else in the driver’s seat. Even if you drove well, he’d criticize you for taking the wheel. Ed’s a smart, creative entrepreneur who’d hired top-shelf people and built a successful company. He could make great decisions. And he hadn’t always behaved this way. What was going on now?

Ed’s super-charged imperative to call the shots, I came to understand, was originally shaped by his growing up with a sick father and having to care for his younger brothers while their mother was off working. It’s not all bad; that history played its part in propelling him to work hard, build his business, stay healthy, and take care of his boys. But it also generated a need to never feel incompetent or weak.

After a time, Ed confided to me that he was privately considering stepping back from the helm, and was assessing his senior team for a potential successor.

The possibility of relinquishing command – an unspoken and undecided decision – was the spark for Ed’s seemingly inexplicable down shift in leadership. Though a potentially positive move for him and his company, it called-up a dire backward-looking vision unrelated to business: his being the absent father and letting his family/company collapse.

What to do? Ed’s recognizing there was something he couldn’t figure out – which actually went beyond what he thought it was – and then reaching for assistance was its own difficult decision. Looking ahead, Ed need not reveal his intentions regarding stewardship before he’s ready to. But he has to understand that the mere idea of it is causing reactions in him that are already adversely impacting his senior staff and their work together. Reconciling his ambivalence about what he’s planning will enable Ed to devise ways of redistributing power and authority so his managers can play to their strengths. Likewise, they need to stop passively ceding their assets to keep Ed from unraveling, and get back to business.

So what can you think about when facing important decisions?

Every decision is situationally distinct, with its own unique sets of ingredients, parameters, and ramifications. There’s no shortage of pundits bloviating on the golden rules of being (or appearing) decisive and vivisecting leaders who are not. But static generalized guidelines about how to be a leader who makes excellent decisions are usually situationally useless. Good decision-making is a learned, entirely individualistic process. Knowing more about how you operate is part of every successful business owner’s job.

Timing and context can change everything. Ed was treating his executive activities as if his life literally depended on it. At one time in his life, that was true in its own way. But no longer. Even supremely unflappable people can become psychologically disoriented in highly charged moments, and your usual capabilities can slip. So take your time. Agility and decisiveness aren’t in opposition to being thoughtful and deliberative.

Sometimes, the most important part of a good decision is understanding what’s driving you to make it.

What would happen to your business if you were diagnosed with cancer?

Meet Javier de la Uz. In August 2009, while on vacation in Vail, Colorado, with his wife Angela and their four young daughters, Javier suddenly had difficulty breathing. He chalked it up to high altitude, and continued to enjoy his family holiday.

Back home in Rockford, Illinois, elevation 715 feet, Javier dove back into his businesses, ADV Enterprises (which adds value to real estate by urban planning and design and build services), and its subsidiaries, ADV Partners and ADV Real Estate Investments.

The labored breathing continued. Maybe it was asthma, he thought. He was too busy for distractions. But Javier’s chest still wheezed and crackled; Angela insisted he see a doctor.

He finally went on September 8. “I’ll never forget the look on my doc’s face when she returned with the test results,” he told me. “It’s severe,” she said. The diagnosis: Lymphoma. “You’re in for a battle,” the oncologist said. Immediate surgery was required.

Javier barely slept that night. “I had three major concerns: my health, my family’s financial well-being, and the stability of my businesses. My bottom line: If I’m dead, nothing else matters. I decided then and there to focus on fighting my cancer. Other people would have to focus on my businesses for me.”

Planning for the worst 
Javier called an early morning meeting in his hospital room. In attendance: ADV’s senior management team, his twin brother José (ADV’s Field Operations Manager at the time), his lawyer, and his wife. Javier surgically dissected his businesses, indefinitely removed himself as President, and redistributed authority and responsibilities among them.

“When the surgeon walked in, he couldn’t believe I was holding a business meeting.”

That procedure achieved its aim, but additional biopsies brought a clarified diagnosis: Non-Hodgkin Lymphoma Diffuse large B-Cell (NHL-DLBCL). Treatment required a 6-cycle course of chemotherapy followed by radiation.

Once home he suffered multiple side effects of the chemo – constant profound exhaustion, nausea, headaches – the psychological whiplash of being abruptly unhinged from work, the specter of mortality, and a visceral fear of infection.

Catapulted from leadership of ADV, Javier took the helm of combating his NHL. He re-directed his entrepreneurial skill-set – being ultra organized, forward-thinking, and purposeful – to navigating the quagmire of insurance procedures and studying his cancer.

A turning point came when his Oncologist’s office offered a stack of pamphlets instead of answering his questions. “I immediately decided to switch hospitals and doctors,” Javier told me.

He located Dr. Andrew M. Evens, an oncologist at The Robert H. Lurie Comprehensive Cancer Center of Northwestern University, a 2-hour drive from Rockford. “I have 4 daughters, a wife, and my businesses. I want to live,” Javier told Dr. Evens; they met 48 hours later.

New tests showed markers for Burkitt’s, a more aggressive and lethal form of lymphoma. Javier’s new treatment, Hyper C-VAD, amped the nastiest side effects off the charts. He was a dish rag.

A new perspective 
Where are Javier and his businesses now? He’s responded well to the chemo, and his long-range prognosis looks good. While ADV’s overall profits modestly declined just after Javier disbursed management authority from his hospital bed, the businesses rebounded and stabilized.

How is ADV holding its own without him? Among many factors, I think these are the most important:

1. Great staffing: Javier already had key people in place capable of responding to the psychological and procedural challenges of being prematurely thrust into new positions

2. Solid customer and vendor relations

3. Well-constructed and defined business development plans

4. Excellent company values – be honest, responsive, do what you say you’ll do, work hard – which match its people, culture, and market

5. A strong, smart leader who had the good sense to take himself out of the picture so his businesses could take care of business

“It’s been overwhelming but also moving,” Javier said. “My brother José’s not only had to deal with having his twin brother fighting for his life, but has stepped up on no notice to many of my responsibilities in the businesses.”

He continued, “I’d never considered it before, but I wouldn’t have predicted the business could operate so well without me. My cancer has given me an opportunity for a new perspective on organizing my business. I can see the benefit of standing back, and once I’m able to return I’ll think about how I might run things differently.”

Many executives have more than just a deep personal investment in their business; work can be a proxy for their identity and a barometer of self-valuation, with their sense of self-worth yo-yoing with the business’ ups and downs. By contrast, Javier doesn’t feel threatened or marginalized by his managers’ success.

This could just be a healthy but transitory survival response – cancer is the beast to fight now; all others can wait – which will shift once Javier recovers and returns to work. Even if so, he embodies an important psychological characteristic of success: the ability to convert adversity to sustainable achievement.

Javier’s advice to other business owners: “Have a plan, on the business and the personal side, in the event you become ill or die. Have insurance and understand your policies. Don’t wait.”