However, when it comes to the world of entrepreneurship, I am an optimist — and, more importantly, I think that entrepreneurs innately inclined towards optimism. Even more than that, however: I think that optimism is at the heart of entrepreneurial power and success.

Just think about it for a moment. In order to be an entrepreneur, the following is (almost always) true:

• You believe you can defy the odds.
• You beieve that you have something special to offer.
• You believe that you are capable.
• You believe that the hard work and sacrifice is worthwhile.
• You believe that your product or service provides a value to your customers.

No matter how you slice it, those are all extremely optimistic notions. And though a bad day may make an entrepreneur question one or two of those premises, part of being an entrepreneur is coming back again the next day, and starting over.

I was thinking about this as I was reading Jeff Cornwall’s article on MyVenturePad called, “Seeing Things “Half Full” is More Important Than Ever!” He talks about a technique I routinely employ (originally inspired by Tim Ferriss’ book, “The 4-Hour Work Week” and his advocacy of a ‘low information diet’): refusing to be taken in by the bad news, and going out of our way to look at good news.

In his book, Be The Solution, author Michael Strong also points out that with all of the media’s tendancy to focus on the negative, it’s easy to forget that society can and does actually make promising, positive progress on solving problems more than many of us realize.

One of the reasons I go out of my way to surround myself with entrepreneurs is for this reason: I need that energy and optimism, particularly on frustrating days or during complicated projects. As social animals, we are subject to the emotional tides of those around us. And, as an entrepreneur, I can’t afford the luxury of being brought down by endlessly bad news that I can’t do anything about. Instead, I make a choice to be optimistic, and that often means putting a filter on constantly negative news.

In a business seminar last year, a facilitator recounted a story of a fishing trip with his best friend, a wealthy real estate investor. In response to the endless news coverage about the recession, the man said: “Recession! Ha! I chose not to participate!”

Scoff away, but there is something defiantly optimistic in that sentiment — and it helped carry me through 2009. So chin up, and remember: entrepreneurs lead the way, and the best way to do that is to remember that we have plenty of reasons to stay optimistic.

Because of this, most of the entrepreneurs I’ve met in my life have had a strong natural inclination to over-use the word “Yes!” And while that word is never intended to have a negative impact, the reality is that it is often the gateway to a slippery slope that no one saw coming. Michael Michalowicz, of The Toilet Paper Entrepreneur, discusses this in his recent post, The Most Dangerous Word In Business.

The scenario that Mike paints is reasonable one, and worth considering. But in my career, I’ve found myself reliving a different version of the same problem. Envision this scenario:

A big client has a new idea they would like to see implemented. They are excited about it, believes it gets them a competitive advantage, and they have absolute confidence in your ability to get it done. The only danger is that, in order for it to do any good, it must be done in a month. Any later than that, and the window of opportunity has closed, and the whole thing has been for naught.

You look at their request, agree that it would be a valuable differentiator for them and agree that it’s entirely doable… but you also see that it’s more complicated than they are assuming, and that a month to get the whole thing turned around is ambitious to the point of being risky. Your gut reaction is, “If only they’d asked me this 2 months ago!”

And then your brain starts to churn… “How could we get this done in time?” “What would we need in order to shorten the timeline?” “Would we be able to split the work across more resources to get it done in that amount of time?” And then the doozy: “If we did X and Y, got help from so-and-so, maybe trimmed back the scope just a tad, and everything went 100% perfectly, I think we could pull it off…”

Danger, Will Robinson!

In my world of web development, this is usually where the wheels start to come off the wagon. The trouble is, the most common response is to try slapping them back on and getting back on the trail at full-speed.

Here are the things to remember when you hear the voices in your head trying to talk your gut into saying “yes.”

Nothing Complex Ever Goes 100% Perfectly
I’m sure there must be some type of work out there somewhere that can be counted on to go quickly. But it’s not anything in my universe. Whether it’s software development, change management, people management, process improvement or marketing campaigns, anytime you are dealing with the marriage of people, systems and processes, you are in a complex Bermuda Triangle of potential risk.

There are tons of things you can do to help manage that risk, mitigate it, buffer it and tap dance around it, but all of those things take time and resources. Underestimating the level of effort involved — or, worse yet, assuming it won’t be necessary at all — is like painting a big red bulls-eye on your project and then tempting fate to start taking pot-shots at your efforts.

Expectation Management is Everything
This one is a hard thing for people to remember, but it’s the truth: under-promising and over-delivering makes you credible, reliable and trust worthy. Over-promising and under-delivering unravels all of that — and destruction is always faster and easier than creation.  In other words: it could take you ages to build credibility, but only one misstep to destroy it. A plan that sounds good heading out of the gate, but falls flat before you hit the finish line does no one any good.

Worse yet, in an effort to accomplish the impossible, we often resort to heroic efforts. While that sound noble, it’s also short-sighted. Consider this: if you have a team that is working 20 hours per day to deliver, and even then can’t get it done in time to save the day, then not only have you burned your credibility with your client, but you’ve also burned out your team. If you are relying on heroic efforts to get things done, then you are setting yourself up for being seen as part of the problem, not part of the solution.

People do not like being told no. But, without fail, they’d rather know bad news early so they can plan for it, than to be led down a garden path with a lot of up-front “yeses!” only to discover they’ve ended up in a thicket of poison oak.

Yes Must be Unanimous
The scenario I’ve seen most in my career with startups is that the person who says “Yes!” to a client request is not the (only) person who is going to be needed in order to get it done. (Just about every single CEO I’ve ever worked for falls into this category.)  Before you tell your client “yes!” make sure that you get a “yes!” from all of the people needed to do the work. And make certain everyone is clear on what it will take.

One of the biggest complaints that developers have with project managers is that they are given top-down directions that include timelines they never agreed were realistic in the first place. This is not an unreasonable complaint. The flip-side of that, though, is that far too often, development teams don’t push back hard enough and actually say, “No, that is not realistic.” Instead, it’s too easy to say, “Ok” in a meeting, and then go back to their desk and grumble about it.

The best solution I’ve found to this problem is multi-step:

1. Instead of saying yes to the client immediately, buy a little bit of research time and tell them you’ll get back to them once you know more.
2. Meet with your team and — before telling them what the client’s deadline is — ask them how much time they believe it would take to do the work.
3. Work through the details with the team a bit, so that everyone is comfortable that you are at least in the same ballpark with what you are expecting to deliver.
4. Once you have a timeline that the team feels confident they can deliver, share the client’s deadline.
5. Assuming the client’s deadline is sooner than the team’s expected delivery date, examine the delta. Are there things that could be trimmed out that would make it realistic to hit the deadline? Don’t try stacking a precarious house of cards in order to get to a qualified yes, but sometimes there are ways to whittle things down enough to make it doable.
6. Step through a risk analysis excercise with the team.
7. Identify multiple potential, realistic options that the entire team is confident in.
8. Present several options to the client. Keeping in mind that not one of those options may be exactly what they originally asked for.

The bottom line: all business is about negotiation, and almost nothing is black and white. Be wary of looking at every request in over-simplified ‘yes/no’ terms. The answer to the client’s original request may truly be, “Oh, hell no!” But your response should (typically) be a set of potential compromises for them to chose from. Instead of ABC, it could be A within the deadline, with BC to follow shortly thereafter. Or it could be XYZ as a short-term fix, while ABC gets done in the background for next time.

Whatever the solution, a knee-jerk “yes” is usually the wrong answer if everyone’s gut is screaming “no!” — for both the reasons that Mike outlines in his post, as well as the reasons I’ve highlighted above.

Absolutely: be optimistic, be sensitive to new opportunities, be confident in your team, and be a valuable resource for your client. Just remember that you can’t do any of those things if aren’t realistic about the committments you make.

In The West Wing, one of the on-going themes was how the staff needed to “manage” the President. Whatever his quirks or brilliance, the President was like all of us: a flawed human being with complicated relationships, who was not always easy or pleasant to deal with, who could unnecessarily complicated situations due to his own personal issues, but whom the team respected tremendously. So they were often torn between adoration and respect, and frustration and fear.

This pheonenon is something that renowned business coach and author, Marshall Goldsmith, wrote about in one of my favorite business articles of all time: ‘It’s Not a Fair Fight When You Are the CEO.’ Goldsmith’s point is something that everyone knows and yet rarely discusses: without careful planning and management, leaders can quickly and easily fall into a trap where they are stiffling honesty, innovation and independence in their teams, simply by virtue of sitting at the top of the social food chain.

I was reminded of this when reading Michael Hyatt‘s recent article, “Finding the Courage to Speak Up.” In his post, he acknowledges a fear of confrontation, and how he has had to tackle it in his role as a leader. It strikes me that this is the other side of the same coin.

And in the end, it all boils down to trust. Does the leader of an organization engender trust in his team:

• Do they trust him to let them be creative, independent professionals?
• Do they trust him to be honest with them about their performance?
• Do they trust him to support them in their professional goals?
• Do they trust that he will protect them in the face of unreasonable behavior by clients or vendors?
• Do they trust that he is a source of solutions, and not a contributor to the problems?

One of the reasons that I am a fan of the collaborative freelancer model of doing work vs. the traditional employee model is because, in an ideal scenario, it can require a higher degree of leadership accountability. If I am freelancing with a company, and the team I am working with is being led by someone who is abusive or unreasonable, it is often a much simpler process for me to walk away at the end of a project than it is if I am an actual employee. The model encourages me to be diversified in my client-base enough that it grants me the luxury of more choice when it comes to who I choose to work with.

How many times have employees seen a boss leave, only to be replaced by a new boss? It happens all the time. And it’s often an extremely difficult transition to make. In my corporate career, I have only ever stuck around through that transition one time. Every other time it happened, the working conditions that had made me want to stay in the job in the first place left when my old boss walked out the door. Statistically speaking, more than three-quarters of all people who leave their job, do so because they do not want to work for their boss anymore.

Again, this is a trust issue. And it’s one that is especially vital for entrepreneurs and small business owners. In many cases, you are your small business. And if the people you enlist on your team to build your business are not confident that they can trust you, then you are sunk before you ever get out of dry-dock. In my work with entrepreneurs, the thing I see most often is an entrepreneur who assumes the problems in his business are caused by those around him, and he is reluctant to consider if he could be creating the chaos himself, and the people on his team are merely reacting to it.

The flip-side of Michael Hyatt’s post is that fear of confrontation is not uncommon. Many people will find themselves taking a passive-aggressive position on a problem, merely to avoid a direct confrontation. And if you are the boss, and you have developed a reputation of being difficult or unpleasant to work with, then how many people do you honestly expect to tell you that? Isn’t it more likely that they will just quietly scurry away, and leave you standing alone, scrambling for a replacement?

Building trust is probably the single hardest thing to do, because it requires honesty, setting aside egos, not reacting emotionally and seeking to understand before being understood. Unless or until you demonstrate that you are not only capable of that, but that you’ve cultivated a habit of it, then the people you work with are always in danger of fearing your reaction just enough to avoid being honest with you.

And if you can’t keep people on your team, then who exactly is it that you’re trying to lead?

This is an interesting point for entrepreneurs to consider, because for most of us, we are inclined to believe that asking a question about a customer’s behavior is going to give us meaningful information. To be sure, asking is often far easier and more affordable than watching — especially if we do not get the opportunity to sit in the same room with our customers and observe their behavior.

However, one need only look to several popular industries to be reminded that what people say they do and what people actually do are two different things: diet programs, organizing systems, time management programs, etc. are all large industries based on the fact that what the habits people want to have for themselves are different from the ones they actually have.

In brick and mortar businesses, many of these types of things can be readily witnessed simply by re-arranging physical space: move products around, change the layout of the menu, change the items closest to the cash register or watch how customers interact with your environment. This can be extremely telling, and a good way to know if your customers are likely to grab that Snickers bar as they stand in line to check out, or if they are more likely to order off the Specials Menu if it’s a separate menu than if it’s attached to the regular one.

But what about online businesses? Believe it or not, in the world of online analytics this may be even easier — assuming you know how to set up proper testing, and how to track the results.

A/B testing is a common method used for seeing what really grabs your customers and what doesn’t. The idea behind A/B testing is very scientific: take two virtually identical pieces of content, and then change a single element to differentiate one from the other. Whether it’s the subject line, the color scheme, the main graphic, an advertisement or the font size, this method is a common one to use on landing pages, email campaigns and other published online content. Monitoring the results is a great way to test what your customers are responding to. (Subject lines and graphics are often big factors, by the way.)

The trick to doing A/B testing, however, is being able to track the results. You can start with a free package, such as Google Analytics. You can quickly and easily set up your testing to show you how one option fared versus the other. (If you want to attempt A/B testing for email campaigns, all standard email campaign applications, including WorkingPoint’s partner, VerticalResponse, offer analytics to help you do the same thing.)

I do not entirely agree with the authors that asking your users a question is of no value at all, though. While I can concede their point when it comes to collecting very specific feedback about an individual product, the fact is that most small businesses and entrepreneurs will often find a great deal of value in asking open-ended questions of their customers as a first step.

One of the biggest perils that an entrepreneur can face is the assumption that he knows what his customers really want. While a good entrepreneur may have an idea, the only way to start planning how to iterate on your offering is to start by asking questions. Open-ended questions and on-going feedback are important to understand how to proceed next. I often recommend this to clients, before they start getting more scientific about monitoring results. Otherwise, how do they know what to test for?

Of course, there is another really important reason to start by asking your customers and creating a two-way conversation with them: it shows them that you care. And while that may not be the highest priority for large enterprises, that is a must for any small business to thrive.

Even worse is when I hear this story and then look at the website, only to discover that it’s hideously ugly, has absolutely abysmal SEO potential and looks like it was built in Frontpage in 1999.

Yet, without fail, I hear this story — or some version of it — at least twice per week. And it drives me batty. Some people are just inexcuseably unscrupulous. Most solopreneuers or small businesses do not need a fancy site, but they need one that they can manage themselves. And yet I rarely see “web consultants” do a proper job of educating their clients on how to get what they truly need, vs. just what a consultant can sell and crank out quickly.

Heather Nolte discusses this same issue on StartupNation’s blog, in her post called, “Can a Consultant Save You Cash…and Heartache?” Like me, Heather recounts how invaluable a good consultant can be, if inserted into your business at the right time.

So, how do you know if your consultant is the right person or just the person who happens to be right there?

Don’t Marry the First Girl You Kiss
An old cliche, to be sure, but beware of this trap. It’s far too easy to be so intimidated by a topic that we grab onto the first person who appears to be able to solve it, but try to resist that urge. I met with a man earlier this year who had been sold on the idea of a whole web package for an insane amount of money. By the time I met with him to discuss what the consultant had proposed, it was too late. The client had swallowed the consultant’s story about what he needed, and they were off to the races.

Shop around. Ask for references. And then, when talking to references, ask them who else you should talk to (these are called second degree references and are often the best sources of information).  And, when in doubt, reach out to your network — LinkedIn is especially good for this.  Tell people you are interested in contacts that they can personally vouch for.  You may be surprised how many of them have recommendations.

Teaching vs. Doing
There are some things in our lives that we simply need to know how to do; there are others that are such rarities or specialties that it is unreasonable to expect us to do as well as the experts. In business, this is even more common. Finding the line can be hard, though. And one of the true hallmarks of a good consultant is that they can tell you where the line is in their field.

For instance: A roofer is not going to suggest that you scramble up a ladder to climb out on your roof and re-shingle it after a storm knocks a tree branch down. However, a good roofer should show you how to watch for the signs that re-shingling needs to be done. He should also give you advise about surrounding tree branches, storm conditions and other things that are reasonable for you to keep an eye on.

Finding a consultant who can DO is important. But finding one who can teach you what you need to do is critical. So be sure to ask, “What do I need to know how to do to make this work/keep this working on an on-going basis?” See what they say. If they say, “Nothing.” be a bit wary and confirm that with a few other sources. Very few things are truly maintenance free.

Educate Yourself
In a world of democratized data, real time communication and personal branding, there is no reason in the world that you shouldn’t be able to spend a couple of hours worth of research, doing a bit of homework before you start meeting with prospective consultants/vendors. Before you start talking to individuals, find the industry experts in the field, the thought leaders, the authors and the business experts who service that marketplace.

Things like Google Blog Search and Twitter Search are amazing sources of information, and with a few key searches, you should be able to find out who the most reputable leaders are in almost any industry, and get a little bit of background so that you don’t walk in to meet with a consultant cold. You do not need to be an expert, but you can’t be blind, either.

Always remember: this is your business. You can’t expect anyone else to be as concerned with it as you are — and that concern starts with making sure that you are prepared to ask good questions, and not pay the wrong person the wrong amount at the wrong time for the wrong services.

Last night, I watched an episode from the second season of the British version of the show, and had a great “Aha!” moment. A team of exceptionally talented and well-trained French culinary prodigies working at buidling a fine dining establishment in Inverness, Scotland ran into a strange problem: they had an empty restaurant that couldn’t attract the locals.

Chef Ramsay immediately saw a problem: the ellaborate menu was in French, and the Scottish locals couldn’t figure out what it meant. To make the point to the culinary team, he showed them a traditional Scottish menu of local food specialties and then asked them to read it. The confused French team quickly realized that it was impossible to tell if a menu item held any appeal when you couldn’t figure out what it said.

This is something that I struggle with every day. Words and phrases like CMS, SEO, PPC, Twitter, RSS, HTTPS, PHP, QA, RFP, ROI, CRM, PMO, etc. all come flying out of my mouth faster and more readily than my own name. And it will typically take a few minutes before I realize that I’ve lost someone.

It is often so easy for us to get caught up in our own little world of jargon, that we forget something really important: part of your job as an expert, is to inspire confidence in the people who come to you for your expertise. While demonstrating that you speak the native language of your industry may have value, what is more valuable is demonstrating that you can translate between your language and your customer’s.

After struggling with this problem for years, I’ve discovered three tricks that help re-set my brain back to a normal member of society, instead of just a die-hard project managing web geek.

Network outside of your network
Most of us go to a lot of networking events. The easiest thing to do is to go to events and gravitate towards people who do something similar to you. This is common, because you speak the same language, you understand the same issues and you start off with immediate common ground.

So flip the coin. Go to a networking event that is totally foreign to you. Maybe go to a small business event that targets people of a different industry, or one that specializes in collecting business people across multiple industries. Talk to people. Tell them what they do, and then see how much they understand.

This is great for two reasons. For starters, often times, you’ll see other struggling with the same problem: their jargon doesn’t make sense to you, or other people who are not in their industry. Secondly, it forces you to think about how you speak, because it’s clear that your normal language isn’t their native tongue.

Record a conversation or a meeting
If you know that you are guilty of speaking in too much jargon, try recording a conversation. (Legally, you are required to tell anyone else who participates that you are recording it.) Play back the recording later — a week or so, is often best.

Put down the distractions, and really listen to what you say. Are you tossing out words that are useful to your client, or are you confusing them? Often times we can miss important cues while we are in the middle of a discussion with someone. But if we can experience that same discussion as a ‘third-party’ we can see things from a different perspective. Sometimes this makes it clear that we missed critical clues during the first go-around.

Can you explain it to your grandmother?
When all else fails, especially if you are in a relatively new industry, talk to your grandmother (or someone else of her generation). Can you discuss what you do with them in such a way that they understand what you are talking about, and can you avoid confusing them? If not, go back to the drawing board.

Clients and customers need to feel secure that you know what you are talking about. But they also need to feel secure that you can understand and communicate with them. If you are getting so caught up in your little corner of the universe that you stop being able to communicate in their language, then your value to them suddenly drops like a stone.

Anyone who has ever been married knows that communication is always hardest when you start getting in the habit of making too many assumptions. So stop yourself, back up a bit, and then start over. Conscious communication is not difficult, but it takes focus.

But, then again, so does entrepreneurship.

This creates a whole new set of challenges when it comes to getting work done.  Because information-based work is almost never done in a vacuum, most of us work in teams.  And a large percentage of those teams can go weeks — if ever — without seeing each other face-to-face.  Making this work well sounds like it should be easy given all of today’s technology: email, Skype, ooVoo, Twitter, etc.  But, as usual, the issue that requires the most management is not the technology, it’s the people.

Becky McCray of SmallBizSurvival recently posted an article on MyVenturePad discussing this very thing.  In “6 Tips for managing a distributed workforce,” she discussed several valuable tips in successfully leading a team that is all working remotely (presumably from their homes).  In addition to some of her great tips — ranging from reading The One Minute Manager to explicitly declaring the weekend off — here are a couple more items that I’ve recently been reminded are critical to the success of a virtual team.

Clarifying priorities.

All of us are familiar with the Scope-Resources-Time triangle and we get the relationship between all of them.  One of the most difficult things to manage through is when each member of the team is assuming a different leg of that triangle is the highest priority.  (This can be especially challenging when your priority is your deadline, but you’ve got team members who are perfectionists and want to spend time on things that could be considered enhancements, vs. the most critical requirements.)  To help manage that, I’ve taken to writing a one-sheet project summary for everyone — the client and the team, and the top of the sheet includes the prioritization of those three elements (including supporting notes).

Different projects have different priorities, and everyone needs to know what matters most in order to prioritize options and decisions.  A project leader can’t assume their team reads minds or is going to guess correctly.

Rules of engagement.

These are vital at an organizational level, at a team level and at a project level.  No need to be onerous about it, but it needs to be done.  Things like the Employee Handbook that Becky mentions in her post fall into this category at an organizational level, but having smaller versions at a project level is critical to keeping everything on track.

Things like predictable status updates and check-in times become more and more important to manage if you are working with a team spread across time zones and/or a client with a very formal schedule. This can also mean being explicit about when synchronous vs. asynchronous communications are needed.  There are some things that are just harder to do over email, even though that might be everyone’s preference.

Roles and responsibilities.

This can be part of the Rules of Engagement, but is also a broader question.  A common problem is having several people who are jacks-of-all-trades working on multiple things (this seems to be a particularly common quality among freelancers).  But the the problem which evolves is ownership.  Who is RESPONSIBLE for making sure certain things are handled correctly.

Talk through assumptions.

One of the hardest things about a distributed team is that you are very limited in your ability to witness a person’s reaction to a piece of information.  Whether it’s someone taking offense at a comment and getting angry, or whether it’s taking an off-the-cuff comment literally when it was never meant that way, we rely on face-to-face communications for so much of our understanding of how other people are perceiving what we say.

Figuring out how to do this via technology over distance can be really, really hard.  Rephrasing and repeating back what people just heard is a start, but recognizing that it’s necessary to make sure that people are not taking their communications for granted is a huge part of the leadership of distributed teams.

Ask, Then Decide

Not sure if members of your team prefer email vs. phone calls?  Ask.  Is your designer a morning person and your developer a night person?  Ask.  Does your client spend mornings in too many meetings to be available for questions until after lunch?  Ask.  If your designer uses a Mac, your developer is on Linux, and your client is on Windows, what tools do they like for collaboration?  Ask.  Skype or GTalk?  Ask.

Ask first.  If you do, not only will you be in a position to make better decisions, but you’ll also probably be surprised at how many new things you learn from other people whose experience can come in handy.  If it helps, create a questionnaire for each person to fill out when they join the team, and use that to craft a process that works for that team.  Early morning meetings are not going to be productive if you’ve got a team of night owls.  So make sure you ask first, and then plan.

I love so many things about the distributed team model, but some things simply are harder when working this way.  It is easy to take things for granted, to uncover (and then recover from) casual misunderstandings, and to rely on multi-sensory input to facilitate strong communication when you are working in the same physical space with people.  You can tell when someone is having a bad day, you can see when what you just said confused them, and you can hear how they discuss ideas and concepts in a more casual context to gauge how they are interpreting information.  We often forget how much we rely on casual interactions in the workplace to get things done.

As soon as you move to a virtual team, many of the informal techniques we rely on to communicate are handicapped, if not out-right eliminated.  This means being much more deliberate about how we communicate with each other.  Given that the vast majority of the information exchange in human communications is non-verbal, this is a very counter-intuitive thing for many of us to do.  But if you’re going to make a virtual team successful, it’s something that you’ve got to train everyone — starting with yourself — to do, and do well.

Admittedly, this is a challenge in my life: I am, at my core, a workaholic. I am a product of an entrepreneurial family with a career in tech startups, where working 60+ hours per week (at least) was a badge of honor; I am compulsive enough by nature that it plays directly into both my work style and my ego; and I am a volunteer junkie who is the first in line to take on difficult new challenges that no one knows how to accomplish.

My husband and business partner is the opposite. While he can and has worked insane hours during various points of his professional life, it is not what he enjoys and it is not what he wants. And, for him, my over-and-above hours of work detract from our time together, which is not the trade-off he signed up for.

The VentureBeat article, titled “You work 60-hour weeks. Should your employees?” is probably made even more noteworthy by the comments left by readers. As is often the case, comments fall heavily into two camps:

The What Kind of Slacker Only Works 60 Hour Weeks? Camp — which is the modern equivelant to your grandfather’s old saying, “Back in my days, we had to walk to school a mile in the snow both ways…” It’s a sign of geek and/or entrepreneurial bravado to be the Michael Jordan of work hours, and demonstrate that you can push yourself longer and harder than those around you.

The Work Is Never Going to Love You Back Camp — who are the advocates of “work-life balance” and who are acutely aware of the fact that no one lies on their deathbed saying, “I wish I’d had just one more meeting…” It’s a sign of idiocy to this group that one would ever do anything as foolish as risk their health or personal relationships by refusing simply turn off the computer and leave work at a decent hour.

The thing that is most interesting, though, is that — as always happens in this debate — people over-look a simple, basic fact: different people need different things for different reasons.

In all the politically correct talk about “work-life balance,” there is something important that is often missed: some of us need to work long hours for reasons that have little or nothing to do with anything or anyone else. And, when we find ourselves in a work environment that does not place that demand on us, we will find a way to create it. Consider this:

Work People

• Get their energy from work.
• Derive their motivation from work-based accomplishment.
• Experience their strongest social connections to other people through work.
• Use the inertia of long hours to build momentum for accomplishing their goals.
• Find an intellectual stimulation and satisfaction in work that they don’t find anywhere else.

Life People

• Get their energy from social or personal activities.
• Derive their motivation from hobbies and social interactions.
• Seek social connections that are based on non-work interests, often as part of the respite from work.
• Require the break from work in order to recharge and return productively.
• Experience a wider array of sources that can lead to satisfying intellectual, emotional or psychological stimulation.

And while debates can wage about which side of the coin is “healthier,” it really doesn’t change the fact that my husband is unlikely to ever be an 80-hour-per-week-maniac and I am unlikely to ever be happy trying to keep my work week limited to 40 hours. We’ll each do what we need to do as circumstances demand, but what is native to each of us is different and meaningful for our own reasons.

The VentureBeat article recommends focusing on great results, not the means by which specific individuals arrive at those results. I’d agree with this approach, but take it a step further: it’s not enough to have this expectation of your staff. You have to find staff who want and thrive with high expectations.  Only hire people who like that kind of pressure and motivation.

A “life person” who is asked to work 60+ hours per week by their boss may technically put in the hours, but they are likely to trading in quantity at the expense of quality. For people who need off-hours to recharge their batteries, the point of diminishing returns comes sooner, and time put in working after that threshold is always less productive (sometimes to a costly degree).

Yes, there are always going to be times when the realities of a business require additional time and work, but I think the focus of a boss should be on finding staff whose workstyles fit what you need, rather than trying to turn who you have into someone they are not. In the end, that approach is just asking for trouble, because not only will you always be frustrated — frustrated at having to ask, frustrated by feelings of disappointment and frustrated by the results you get out of people — but you’ll also be setting your team up for failure by creating a situation that runs counter to their individual needs.

Ultimately, you can’t change a person. And asking someone to behave in a way that is fundamentally counter to their nature is never a long-term solution. So my advice is to focus on the fit first. Jim Collins refers to this as ‘getting the right people on the bus.’ If you are a workaholic who likes achieving the impossible at the drop of a hat, then an employee who rolls into the office at 10:00 and rolls out right at 6:00 is probably going to drive you crazy — no matter how much amazing work he gets accomplished in that eight hours.

I’ve worked for extroverted sales geniuses, and introverted operational wizards.  I’ve worked for people who create chaos just by breathing, and for people whose very presence manages to calm everyone without even speaking.  I’ve worked for brilliant absent-minded professor-types, and I’ve worked for walking computers who never miss a single detail.

By and large, I’ve been extremely lucky and have learned a lot from most of them — even if we didn’t always get along or understand how to communicate with each other.

Over the years, something has become clear to me about each of these incredible men and women.  I’ve come to realize that the difference between a good boss and a great boss is the ability to create a legend. That mystique is how a great boss attracts and builds a great team.

Being a good boss is a skill; being a great boss is a talent.

• A good boss helps cover you while you’re on vacation; a great boss kicks you out of the office and forces you to go on vacation when he sees that you need it and aren’t doing it yourself.
• A good boss works with you on your professional goal planning and development; a great boss inspires you to set goals you never previously considered — and then drops challenges in front of you for a bit of added incentive.
• A good boss lets you vent and cry and scream in his office when you’re at the end of your rope; a great boss notices the signs before you hit a boiling point and takes you out for drinks first.
• A good boss hires strong, experienced people and then works to build them into a cohesive team; a great boss looks for talent, develops leaders, sets demanding expectations and then gets the hell out of the way.
• A good boss looks for smart people; a great boss looks for people he believes are smarter than he is.

Great bosses make work worth going to every day, even when the project is late, the client is angry, the team is frustrated and all you want to do is buy a one-way ticket out of town. A good boss is helpful and diligent. But a great boss is who you’d rather walk through flames than run the risk of disappointing.

I was thinking about this while reading Steve Blank’s article on VentureBeat, “Incentives are one thing. Legends are another.” Steve recounts a story where, as CEO, he took financial incentivization to a new level, by generating some healthy, motivating drama around it. And, ironically, he did it by appearing to “not get it” and then pleasantly surprising his team.

What’s good to note about Steve’s story, is just that: it’s a good story. And, especially in the early days of a venture, sometimes we need good stories to help propel the mystique enough to keep us moving through that tough uphill climb.

When I think back to my early days in startups, the power of some of those stories still moves me. Whether it was a client story or a team story or some other story, human beings are drawn to stories because they are experiential and personal. There is a power to having and cultivating good stories when you are a startup, and it’s all part of what Steve shared in his memory: successful people take enormous paycuts to do inhuman amounts of work to achieve heroic efforts. And while there are definite ego strokes to be had by success, there are small touches that don’t cost a lot, but which can make the difference between a “good” experience and a legendary one.

As the boss, part of your job is to build a company that can retain talented, energetic people — especially when the outside world can offer more immediate, tangible motivators than you can. No company can thrive if your best team members lose interest and walk out the door. So how to do make sure that your people remain engaged, despite insane amounts of work and huge personal sacrifice?

Steve’s advice is good: find ways to build the legend. It’s not as hard as it may seem, and — even when money is tight — there are ways to do it that require more in the way of attention and consideration than actual dollars and cents.

And, in the end, the biggest difference is simple: a good boss is content to have a happy team; a great boss is only satisfied with an inspired one.

This comment reminded of Jonathan Fields’ article from a few weeks ago, “The Delusions of Entrepreneurs,” in which he explored what made so many of the trappings of entrepreneurship a bit more myth than reality — including notion of freedom, control, money and passion.

Jonathan’s points were all valid: starting your own business can put just as many shackles on you (or even more) as working for someone else, they are just different. And I think this is the point that really matters, and which the senior Adler was making about his son: if you are not good at following rules, then it’s very hard to get ahead in someone else’s business.

Now, to be fair, there is a certain amount of rule following that we all need to do to be successful in life: if I make a habit of driving on the left side of the road (in the US), odds are good that my professional success is going to be hampered by turning myself into road pizza before I can launch my product.

However, if my aversion to rules is more subtle — take, for instance, a compulsive need to be more direct and honest than is politically correct (which happens to be true) — then it’s easy to see how having my own business probably has better odds of success than me trying to work for someone else. There will always be people who consider my directness to be uncomfortable or impolite, but if they are clients or colleagues rather than a boss, then we can go our separate ways agreeing to disagree, instead of miserably trying to stay in a professional marriage that doesn’t meet our needs.

Another reason that I think John Adler’s point is valid — and one of the things I think Jonathan Fields missed in his reasoning — is that when you have your own business, you get to determine what “success” means to you. If you are working in someone else’s business (especially a large enterprise), what constitutes success is often prescribed by someone who came before you. If you have your own business, then you get to draw the map. Sure, you could find yourself stranded on a ledge somewhere, but that’s equally true when you work for someone else.

• Is your definition of success making a ridiculously large income?
• Is your definition of success being able to sleep in until 10:00 a.m. every day?
• Is your definition of success being able to sell your company and retire?
• Is your definition of success having 50 employees? 100? None?
• Is your definition of success revolutionizing your industry?
• Is your definition of success being a leader in your community?
• Is your definition of success having the time to do volunteer work?
• Is your definition of success being location independent?
• Is your definition of success being able to take your dog to work?
• Is your definition of success getting to work with your family/friends?
• Is your definition of success having the flexibility to go to your kids’ school events in the middle of the day?

We all define success differently, because we are all motivated by different things. Owning your own business gives you the change to attach what motivates you to how you are going to define success, and the drive your business towards those goals. When you join someone else’s business, you are agreeing to their destination.

And, if like Trip Adler, you’re too much of a ‘free spirit’ for someone else’s rules, then starting your own business may just be the only rational choice you could make.