As a career management advocate turned Entrepreneur Evangelist, I recently had an epiphany that clarified some of the change I’ve experienced over the past two years, as I’ve moved from my old life to my new one.

I’ve been lacking an effective metaphor to describe both the process and my present (and potentially future) state.  This has been tremendously frustrating (for both me and my husband), because my state of mind on this journey radically colors the choices that I am (or am not) comfortable making.

I think I finally figured out how to define it more effectively  We often talk about a “career path.” I think this is inaccurate. I think the right phrase is a “career highway.”

Right Lane = Stability-Motivated Employee

• One career and as few employers as possible.
• Stability reigns supreme.
• Even calculated risks are uncomfortable.
• Large enterprises and government positions often appeal most to this category.
• A single employer career with a stable retirment plan and reliable benefits is the Holy Grail, and boredom is acceptable at work in exchange for stability.
• Any necessary excitement can be sought outside of work when needed.
• “Progress” is most frequently measured in proximity to retirement, more than rungs climbed up a career ladder.

Second Lane = Migratory Employee

• The modern normal.
• An employee who will have 2-4 careers in a lifetime, and an average of 12-15 different jobs.
• Stability is important, but not above all else.
• Calculated career risks are worthwhile, if not occassionally exciting.
• Jumping to a new job is always a possibility if a more appealing opportunity presents itself.
• This employee is often heavily motivated by autonomy and new challenge, secondarily by money.

Center Lane = Freelancer

• The newest class of employee, often placing a premium on freedom and flexibility above stability.
• Often easily bored, and prefering variety with risk to stability with stagnation.
• Commonly enjoys being a solo entity, and is disinclined towards growing a business that requires taking on the responsibilities of having employees.
• Collaboration with other freelancers is often a successful and preferential model.
• “Dollars for hours” is the most common financial model, which can cause business development challenges.

Fourth Lane = Self-Employed

• Small businesses, often family or small-team owned/managed.
• Frequently limited in scalability.
• Often heavily reliant on founder(s) for success.
• Lifestyle businesses and brick-and-mortar neighborhood businesses often fall into this category.
• Not uncommon for an owner to discover that they ‘own a job’ rather than ‘own a business.’
• Freedom and wealth-building often started out as core priorities; over time, the realities of business limitations can undermine those objectives if this was not the intended final growth state of the business.

Left Lane = Business Owner

• Scalable businesses of all sizes.
• Owner/founder has decentralized systems, processes and critical knowledge enough to allow for empowerment and delegation among staff.
• Vacations and sick days for the founder are possible and cause little in the way of organizational chaos.
• This business is a strong candidate for potential sale, since success is not wholly dependent on the original founder for success.
• Owners/founders who build this type of business can/do often build more than one over the course of their lifetime.

Obviously this isn’t an entirely clean mapping, and different combinations can blend a bit to create a bit of a hybrid. But I think that the most meaningful part of the highway metaphor is the idea that people can change lanes over time. Different life factors can influence which lane someone chooses.

• I have seen dozens of female Second Laners have children, and then suddenly switch into either Right or Center Laners (depending on both their personality and their skillset).
• I have watched numerous Second Laners get laid off and decide to take on an entrepreneurial opportunity by moving immediately to the Center Lane, sometimes working their way farther over as time goes by.

This has been my path. I was an obsessive, workaholic Second Laner who was finding a ton of meaning and fun in the career that served me well, paid me nicely, stroked my ego constantly and took me on great professional adventures for a decade. When I hopped off the highway to move to a new town, I (arrogantly) assumed that I’d be able to just hop onto the new road in my new town without any trouble, and slide right back into the Second Lane again.

Unfortunately, my timing sucked. We left New York for Texas the week that Lehman Brothers decided to implode under the weight of their reckless decisions, and all of my pre-move job interview work collapsed with it. While not technically laid off, I found myself in the same position as many people who were: I was suddenly at loose ends with an inability to find a company that would let me do what I knew how to do. So, I shifted to the Center Lane.

The reality, though, is that at the time we started our business, I used the language that I knew my husband wanted to hear: and it was all Left Lane language. That’s what he wanted, that’s what he was going for, and that’s how we discussed it. The problem, of course, was that — like many new Center Laners — my hope was to bide my time until I could jump back into the Second Lane.

After a rough few months, I was finally given that chance. And, as luck would have it, it was on a trial basis. My new employer wanted the chance to check me out, and I certainly wanted the chance to check them out. As it turned out, that was the best thing that could have happened to my Career Highway Navigation. Going from the Center Lane back to the Second Lane suddenly felt painfully confining. Stifling, even. I was miserable within a week. I never saw that coming, and was a bit shocked to finally get what I’d wanted only to discover that I didn’t want it anymore.

So, after informing my employer that I didn’t foresee being able to sufficiently fill their needs, I stayed around to help them hire my replacement and then ultimately left. Back in the Center Lane again, I was at loose ends once more, but this time with a purpose. I just had to figure out how to make it work.

During this time, my husband began working on his startup. Everything about my husband is Left Lane. The idea of any other kind of business simply doesn’t make sense. And as a deeply collaborative person, he recognizes that he’ll need help to build a business that fits the bill.

Yet when it comes to me, in my professional life, I’m still in the Center Lane. I know that I don’t want to be in the Fourth Lane. But I’m honestly not sure that I want to be in the Left Lane, either. There are variations of the Center Lane model that are more lucrative and more sustainable than a strictly ‘dollars for hours’ model (which I also don’t want), but I’m not at all convinced that I can’t attain the degree of freedom I am looking for, accomplish the wealth-building I seek and manage to stay in the Center Lane.

But then, that’s part of the point: my A-#1 priority is freedom, above all else. I am not risk adverse (obviously), and I enjoy primarily being an individual contributor who occassionally collaborates on larger projects with others; I also don’t want to go back to managing people, projects, processes or products (been there, done that)… but I also don’t want to go back to working for anyone else. Given that, I don’t really see a solution other than the Center Lane for me.

My husband’s priority is to change the world, build a team of empowered collaborators and inspire the people who come into contact with his business to find creative solutions to large-scale problems. This is a goal he could never accomplish from the Center Lane. To do this on the scale that he wants, he needs to be in the Left Lane.

I always like the way the Left Lane looks. But I am increasingly less convinced that I’ll ever necessarily make my way all the way over there. But I’m also increasingly less convinced that I necessarily need to. With some proper planning and organizing, I could find that the Center Lane is the place that I’m happiest. Only time will tell. I just hope that next time I find myself switching lanes, I’m aware of it in time to turn on my blinker.

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As my year-end consumption of ‘top ten lists‘ continues, I came across one on Chicago Now called “The Top 10 Small Business Trends of the Decade” by Barry Moltz.  In the list he mentions several things that have all dovetailed together to define the changing nature of work — most centered around the pros and cons of mobility.

While I certainly wouldn’t argue that his list is wrong, it is very similar to several others I have seen, and I continue to think these lists are only peeling back the first layer of the onion.  Barry’s list includes items in three basic, separate categories:

Mobility:

• The internet allows geographic independent sales and marketing.
• The movement to reduce costs and commuting by working at home.
• Mashing of work and home spaces.

Social web:

• We are more easily able to network and keep in touch with people from our past.
• Size no longer matters.
• Customer Service makes a comeback.
• You are your own brand.

New economy:

• Less credit, more cash is king.
• Less benefits, higher deductibles.
• A new class of employee appears.

The details that Barry highlights in each of his bullets just grazes the surface of these bigger buckets.  And, even more significantly, these are revolutionary social changes that effect all business, not just small business.  What I find more interesting is their unique influence on small business versus their broader social impact.

Mobility
Obviously there is no one who has to be convinced that the second generation of the internet, with it’s capacity for permanent mobility, has changed everything.  Socially it means that states and municipalities have to pass new laws about using cell phones while driving; large business has to implement both policies and infrastructure to support workforces that are increasingly likely to be conducting work outside the corporate firewall; and small businesses can get up and running without having to see their opportunities limited by where they prefer to live.

But the bigger implication about mobility for small business is, I would argue, “the cloud.” Cloud computing (in its broadest definition), and specifically Softward as a Service (such as WorkingPoint, VerticalResponse and Business Online Payroll), is a double-edged sword in the world of small business.  Not only has it made tools and resources that used to only be available to big companies financially accessible to small businesses, but many of these companies are themselves small businesses.

The fact that a couple of developers with a great idea and some solid experience, can now leverage enormous outsourced technology infrastructure to build, host, manage and ultimately distribute their product to anyone in the world is revolutionary.  The cloud has extended everyone’s reach and has eliminated several of the biggest barriers to entry that existed when I started working on the technology space back in 1996.

The Social Web
This, of course, is this year’s hottest topic.  The social web went from being an outlier, specifically and uniquely for either early adopter tech geeks or Gen Y young’ins, to being super hip mainstream, ‘cutting edge’ mass media.  As Barry notes in his list, this has made a huge impact on how brands need to function in order to maintain their integrity — both on a personal and a business level (re: his points about customer service and company size).  But what’s the real seismic shift here?

The true impact of the social web is privacy.  Or, more accurately, the line between private and public.  Never before has it been more blurred, and it’s going to get more confusing before it gets less so.  Therapists will often point out that it only takes one person in a relationship to change the entire relationship dynamic: if you change your behavior, then it forces the other person’s behavior to change as well.  This principle is seen daily on the social web.

When customers change their behavior, it forces business to change.  Hence changes we see in the realm of customer service: a person can complain about a brand experience they had on Twitter, and see anything from immediate resolution to a lawsuit, depending on how the brand in question decides to handle things.

When employees change their behavior, it forces employers to change.  Businesses cannot reasonably ask their employees not to participate in the social web.  So how do they handle react when one of their employees becomes a bit of a social media celebrity, whose personal brand radically out-shines the company brand?

When citizens change their behavior, it forces the government to change.  “Transparent government” and “Gov2.0″ are two other key watchwords from 2009 that were nearly unheard of a year ago.  But now that individuals have come to expect to know things about the companies they deal with by virtue of online information, that expectation has transfered to government activities as well. Two years ago, who would have thought that Congress would have it’s own YouTube channel?  Or that a presidential candidate’s success could have been largely impacted by the use of Twitter?

Where is the line between private and public?  Tools that started out as personal use tools (e.g. Facebook and Twitter) are now platforms for business innovation.  The line between the two is different for everyone, and that creates a challenge, because the choices that one person makes will impact other people, whether those other people like it or not.  How many times have you seen someone post a picture to Facebook or Flickr that includes other people who may not have wanted the picture posted?

There is a certain amount of privacy that a social web automatically steals from us.  The questions are how much is necessary, and then how much is comfortable.  The tricky part is that depending on the application and the person, those answsers change.  And only being in the first generation of the social web, we are a long way from sorting out those pesky little details.

New Economy
My favorite topic of all, is the new economy (which I would define as the economic realities inherent to our modern lives as a result of, among others, the two factors above: mobility and social web).  But this is also the one that is routinely most difficult for people to get their heads around, because the ripple effect is pervasive, throughout every facet of our lives.

Old definitions no longer apply: “conservative” versus “liberal” are ill-fitting labels in a world of updated economic and social conditions that re-draw the political lines without even trying.  Words like “stability” and “security” are no longer applicable to the job market, after three decades of being considered the corporate Holy Grail.  And in a nation that was spurred to global dominance on the back of an Industrial Age economic engine, a nation of “knowledge workers” now routinely offshores work to less expensive parts of the world on a daily basis.

There are some pretty enormous downsides to the new economy — no more pensions, no more covered healthcare, no more job security.  But there are also some amazing opportunities in it — no more being stuck having to live someplace you don’t want simply because of its proximity to your job, no more expectation of having to let someone else define your rise up the corporate ladder on their terms and timelines, no more wistfully dreaming of being your own boss because it costs too much to start your own business.  Think of it like sky-diving: for some people it represents the most terrifying nightmare imaginable; for other people it is the single biggest thrill they could ask for.

As with most change, the pros can be just as compelling as the cons, depending on your point of view.  Socially speaking, the new economy means that goods and services that used to be out of reach for the average person are now vastly more affordable — everything from international travel to high tech toys.  For large enterprises, the ability to offshore entire divisions of your business means huge cost savings, and leaner in-house talent able to focus on the most high-value added functions.  For small business, the ability to dynamically pull together freelance, geographically distributed teams to execute on projects as needed, means being able to compete with larger firms without having to take on the overhead of formal staff.

So, yes, Barry’s list of small business trends is technically accurate.  But the reality is that the changes his list represents are even bigger.  And the reason they have such an enormous impact on small business is that these factors have already fundamentally shifted the social foundations on which small business is built.

This post originally appeared as part of my Entrepreneur Evangelist series on WorkingPoint‘s Small Business Blog.

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I love startups. I love the chaos. I love the insane hours. I love the energy. I love the types of people who are attracted to work on high-risk ideas with long odds. I love the culture that evolves around them. I love it all. I have spent my career hopping from one startup to the next, because there is nothing I love more.

But every startup hits a tipping point, and it’s rarely articulated as clearly and beautifully as Steve Blank does in an article posted to VentureBeat today. The transition from a ‘scrappy startup’ to a mid-sized company trying to be more mature is always infinitely more painful a process than anyone seems to think is reasonable.

This surprises me every time I see it. In his story, Steve recounts watching a new CFO to a mid-sized firm implement a ‘no more free soda’ policy and inadvertently spark an exodus of the founding team of engineers. What’s more interesting, though, is that some of the comments posted on the story miss the point: the engineers didn’t leave the company because the company started charging them $.50 for a Coke. The engineers left because being charged $.50 for a Coke was a sign that the company was no longer the same organization that they’d previously been willing to sacrifice for.

That’s a subtle distinction, but a vital one. More than once, I and many of my colleagues, have been willing to take significant pay cuts to work in environments that had a culture (or other intangibles) that made the trade-off worthwhile. Eventually, though, most organizations change enough to where that trade-off ceases to be worth it. The part that is often upsetting, however, is that those changes are frequently sparked by someone coming in the door more intent on shaking things up than on understanding the culture they are walking into.

Steve’s story is one that I can relate to over and over again. It wasn’t until I had a truly remarkable executive come into our organization, and refuse to act precipitously, but instead insist on watching and interviewing the entire staff for his first 60 days, that I had the slightest hope of someone making positive changes without unraveling the cultural elements that held us together, even in the face of the chaos. So now, when I go into startups, many of which are at the transition point between early-stage/founding team, and their second generation, I have a five step approach I follow:

1. Recognize that, for founding teams, everything is personal. The people who build a new organization take on a lot of risk and chaos to do it. They have to believe in it. It’s almost a religious experience, and you can’t come in a year or two later and expect them not to take your changes personally. Because, whether it makes sense to you or not, everything is personal. They’ve sacrificed too much for it not to be.
2. Understand the evolution. You have to be a bit of an archaeologist when you go into a new business. Do not make assumptions about how they got where they are. If you look long and hard enough, talk to enough people, and do your research, you’ll find that even the craziest things you see have a reason for having evolved the way they did. Unless or until you understand that reason, anything you do to try to “fix” the situation runs the risk of alienating people unnecessarily.
3. Respect the sacrifices made by the people who came before you. Unless you know that the people who are there when you walk in the door are dead wood and you want them to quit, make sure you demonstrate some respect to what they were able to accomplish — especially if they did it under tough circumstances. The single biggest source of alienation I have ever seen has been when new people come in, hot-to-trot, making changes and the people who built the company in the first place are treated like morons who simply got lucky.
4. Work on depersonalizing the business. It is reasonable that early stage startups are often personal sacrifices for people — they need to be. But a maturing company has to pass the point where that is no longer true. Not all of the early stage team will be able to handle that transition, but many of them can and will if they do not feel kicked in the teeth by new leadership brought in from the outside. Slowly building in an ethic of, “It’s not personal, but this is where the business needs to go now” is actually often much easier than people assume it to be. Founding teams want the business to be successful. That was the whole point for their sacrifice. If you want or need them to stick around, then help them learn to take a step back and not see the evolution of the business as an emotional affair.
5. Facilitate relationships between the old guard and new guard. Not all of the old guard is (or should) make the transition to the new phase of the business. And not all of the new guard is capable of showing any respect for what the old guard has done. But if you focus on individuals, their talents, and understanding what drives them, it is often possible to help connect people in ways that build strong teams to move the company forward. But you must keep in mind that there is often an automatic lack of trust between both groups, a tendency to point fingers, and a common tradition of resentment that you must work through before you are going to see progress.

Businesses are made up of people. And not every person is right for every business at every stage. Some really do need to move on as an organization grows. But that should be a deliberate, well-considered decision, not a haphazard, expensive mistake spurred by a short-sighted, penny-pinching reason. Unfortunately, that’s the cause I’ve seen most frequently throughout my career. And it’s a bit tragic, because a lot of dynamic organizations have lost a lot of amazing talent that could have helped grow the business and make it successful.

(This post is part of my Entrepreneur Evangelist series and was originally published on WorkingPoint‘s Small Business Blog.)

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Many people don’t think about it specifically, but know it intuitively: if you want good customer service, skip the big guys and go to a small company. In Small Business’ Competitive Advantage, I discuss that Customer Service is the magical pixie dust for small business.

Think about your normal daily experience: if you need to deal with your bank, your insurance company or your utility provider, you call an 800 number, where you are greeted with an automated message, a phone tree that routes you through a series of menus, as much automated information as they can possibly prepare, and then — if you’re problem is too complicated to automate — eventually you may get a person.

And then what happens?

You have to repeat your account number, despite having entered it already (at least once); you have to answer questions to validate your identity (or, worse yet, you don’t, which always begs the question: who else can get into my account?); and then you can get around to your question.

In many cases, by the time you get to speak to a real person you are dealing with a call center on the other side of the planet, non-native speakers (who sometimes struggle mightily with English), and in worst case scenarios, people who are clearly reading from a script with very little real understanding of either the nature of your problem or how best to handle it.

And when it’s all said and done, how often do you go through all of that, and get off the phone feeling totally confident that your issue was resolved? Rarely. More often than not, most of us get off the phone feeling like we just got the run around so badly that we need to double and triple check our next round of statements to make sure no one messed anything up.

All in all, because of the economic needs for businesses to automate and off-shore customer service functions, the general state of Customer Service is often crap.

This is where small business owners can be Superman. Seriously. For most small businesses, we don’t have the volume to go through all of that expense and hassle. Our customers often have our direct phone number. They know where to find us, how to reach us and what our specialty is. And while that may not always be great for our daily productivity (and it can certainly be abused at times), it gives small business owners the chance to leave our customers with a far, far better customer service experience than the one they just had with their credit card company.

We talk so much about business that we often over-look the most important fact of all: business is conducted between two or more PEOPLE. Sure, there are functions that can be automated and there are often good reasons to do it. But when you leave your customer feeling like less than an actual person, you’ve just provided a lousy customer service experience. Small businesses, because of logistics, have a built-in advantage. And it’s one we should all remember to take advantage of.

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I’ve been feeling nostalgic this week. After so many years in ecommerce, supporting catalogers and retailers whose year entirely revolved around the Christmas season, I am almost at a loss for what to do if I’m not running around putting out fires from Thanksgiving weekend up until the week before Christmas.

Strange as it seems to most people, I loved the chaos of the holiday season back in my MarketLive years (2000-2005). I really did. It was high drama, high anxiety and high chaos. All the delicious things that a good single workaholic who lives four blocks from the office craves.

And what was even better was that we knew it was coming, so we got to anticipate it for months before it happened. It was like standing on a beach, watching a huge wave build and build as it rolls towards you and just standing there, bracing yourself, waiting to see if you’re going to be able to keep your footing.

Since so many of my core strengths come to the surface when it’s time to put out fires, it was a natural time for me to hit my stride. In hindsight, I can clearly see that some of the reasons I enjoyed it so much played into some of my less healthy habits. It was still a hell of a lot of fun, though.

Hub in the Wheel
Particularly during my years running point for IT Hosting and Operations, I always got to be in the middle of everything. If I’d had what is euphemistically referred to as “a healthy work-life balance” (a term that makes me crazy), then I wouldn’t have considered that a perk. But, since I didn’t have a life outside of work and since I had a huge ego, being in the middle of everything all the time worked very nicely for me.

Troubleshooting

When things go wrong on an ecommerce site during it’s busiest weeks of the year, any minute of outage is a potential disaster. So every second counts. What I loved about the holiday season is that we ran at a fever pitch, so when anything went wrong, the best troubleshooters in the company were all collected together to figure out what was wrong and how to get it fixed.

At the age of 27, that was one of the greatest experiences I could have asked for. Not only did I learn how to troubleshoot better than almost any professional I have ever worked with since, but I did it with other brilliant, creative, talented people who were also good at it. Part of me wishes I hadn’t taken that skill for granted so much back then. It would be years later before I understood how remarkable a team we had, and how amazingly gifted they were at it.

Making Things Happen

There is nothing I find more gratifying than progress. Like many project managers, I love making lists — simply so that I can cross things off of them. It’s something I find profoundly satisfying. One of the greatest things about the holiday season in my ecommerce days was that suddenly process took a back seat, obstacles were knocked down, priorities were re-oriented and all that mattered was getting something DONE.

Friends

To this day, I have never worked in an environment where I had as many close friends. It was the foxhole mentality. It’s common in the military and political campaign teams. And startups.

Those of us who used to deal with the fires spent insane amounts of time together: we ate together, we argued, we got punchy with each other, we got punch-drunk until we cracked up laughing at 3:00 a.m., we worked 24+ hours straight together, we called each other in the middle of the night to get help with issues. We made each other crazy, we made each other laugh, we made each other smarter. It was awesome, and I’ve missed that rare combination of talent and circumstance ever since.

Like many people, the older I get, the more nostalgic I get about times gone by. I’m lucky that for much of the craziest part of those times, I actually really loved it in the moment — not just after the fact.

It never fails now, though: I see the polished world that ecommerce has become — all marketing and very little tech — and I see the predictions about what kind of sales Cyber Monday is going to see, and I think back to my late 20′s when that was my life.

It makes me proud to think about all the crazy things we managed to pull of with no safety net. It makes me sad that I don’t go to work with those same phenomenal people every day. And it makes me happy, now that I’m a little older and a tiny bit wiser, that I don’t have to be on-call, anymore.

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In Deck the Halls with Pink Slips I discuss the November round of layoffs at several big companies. Of course, part of what brought these to my attention is that a dear friend of mine got caught in the pre-holidays cut-backs at Adobe.

Even worse, however, was the fact that my friend loved working at Adobe. It was the first time she’d worked for a large company, so some of the perks that big company people take for granted — training, resources, perks, etc. — were all relatively new to her, and she was taking advantage of as many of them as possible.

While it’s probably unlikely that my friend is going to go off and start her own business at this point, I got to thinking about the hundreds of people who got the ax: what that meant to their holidays, their lives, their plans and their next steps.

Since a great many of the layoffs were in my beloved Bay Area, it’s unfortunate to realize that the already over-whelming glut of talent on the market is now going to be competing with an even larger pool of newly “free” talent for an extremely small number of jobs. Especially as we head into the end of the year, where many places are in a holding pattern until the beginning of Q1 (though, admittedly, many of those who do not intend to bring anyone on until after the first of the year, will be looking and identifying their new hires now).

I wonder how many entrepreneurs have just been unleashed. Maybe they are people who have wanted to start their own business for a while, but who weren’t ready to walk away from a steady paycheck to make it happen. Or how many are like me: reluctant entrepreneurs responding to circumstances first and foremost.

I look back on this past year, realizing that my journey has landed me somewhere I never imagined: happily self-employed. I certainly didn’t start out that way. I fought it, kicking and screaming, making my husband crazy, making myself miserable, worrying my friends and family, and generally resisting being knocked out of my comfort zone.

And now I wouldn’t trade it for the world. I don’t want to work for anyone else, and I can’t think of anything less appealing.

My holiday wish for the people who found themselves on the receiving end of some holiday uncheer is that they find the courage to take advantage of the opportunity. The era of big business is over. Now is the time to either start your own business or join someone else’s startup. And if you can do it while you’re still getting a severance, then even better: let your former employer help pay you to get a new business off the ground!

Self-employment isn’t for everyone. But I do believe that, for those of us with a strong inclination to take charge (and/or a strong aversion to following directions from others), eventually the opportunity will present itself and, given the right circumstances, it’ll prove a far more enjoyable road than the same-old-same-old.

Besides, we’re in the Information Age now. The same-old-same-old is dead. Thank gods.

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Some questions are just a trick. The interview process is full of these: there really is no right or wrong answer. The point is just to read something into which option you pick. My favorite of these is the famous one: “Which is more important to you: being liked or being respected?”

As a boss, project manager and organizational leader, the problem is that this question is a bigger trick question than for the average person. I am someone who is expected to get things done. Now, the reality is, most of those things I do not do myself. I get them done by organizing and mobilizing a team of specialists to execute against a plan of action. So that means that my success is dependent on other people.

One of the first lessons I learned as a 24-year-old project manager was that it does not matter which I prefer. What truly matters is what my team needs. And the real danger to this question is that different people need different things.

I used to have a gentleman on my team who was notoriously prickley. Being friends was not part of his MO when it came to work. He had a job to do, he was there to do it. Fuzzy friendly stuff was of no use to him. What was important for me was to understand that. Who cares if what I want is to be liked? The fact is that trying to get that guy to like me was not what he needed from me. All he cared about was respect — whether he felt respected and whether he respected the people around him. “Like” was not part of his equation, and people who wasted time on it were not ones he respected.

Conversely, I had another person on my team who needed a ‘big sister.’ He needed a boss (to be sure), but he needed one with velvet gloves: someone who could be sensitive to his needs, who could guide and advise him, who could encourage and support him, who could help him make plans to meet goals, etc. Yes, he respected me. But that was only possible because he liked and trusted me first and foremost.

One of the biggest failures I see in leaders is assuming that one-size-fits-all leadership works. It doesn’t. People are not IT systems. You can’t configure them to your convenience, turn them on and then walk away.

If you have people on your staff, they are individuals working for an individual — and you failing to meet their need as a manager is the single biggest cause for their departure. So the best way not to fail, is not to assume that everyone responds to the same carrots the same way. Some really do prefer the stick.

So these days, my answer to the question of whether I think it is more important to be liked or respected is simple: “Who cares what is more important to me? The question that really matters is, ‘What’s more important to my team?’”

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As the old joke says, “There are two kinds of people in the world…” In my corner of the universe, there are those who love working in/with startups and those who don’t. Those to love it never question why someone else likes it. Those who have either never done it or who have low tolerance for chaos rarely understand it.

This question came up again today, and I found myself — once again — struggling to provide sufficiently insightful answers to the questions about why I like highly chaotic startup environments. And, once again, I have found that the people I speak to are often convinced that their startup is the most chaotic in the world. There is often enough of a badge of honor built into that assumption that I try to avoid disillusioning people by pointing out that it’s probably pretty unlikely that their brand of chaos is any “worse” than that of other startups.

But the fact is that everyone assumes their brand of chaos is the worst. I spent five years at a self-funded ecommerce startup and most of the time I was there I had two official jobs. Every couple of years I would change roles, but yet it would take more than a year to offload my old one. But, I was young and hungry for opportunity, eager to prove myself and perfectly willing to take on that insane level of work (despite my staggeringly small paycheck).

Later in my career, at another startup — this time an airline — I found myself (along with all other employees who worked in HQ) standing at JFK international for five days dealing with irate customers in the most face-to-face manner you’ve ever seen in your life. Those five days cost the company over $30 million. The results of that, of course, were more chaos: the Board ousted the CEO, and the entire organization set about a massive set of initiatives designed to prevent that level of chaos from ever impacting customers again.

And yet, despite years of sleeplessness, no social life, below market rate salaries, extreme stress and constantly disrupted vacation plans, I keep coming back to startups. Why? Because, as one of my former bosses always used to say, there is opportunity in chaos. Tons of it. There is always far more opportunity in chaos than in calm.

People who seek out calm, mature, stable environments do that because it is important to be able to walk out of the office every night at 5:00 p.m., it’s not because they are looking for unforeseeable opportunity born out of crazy left turns and unpredictable technology shifts.

Everyone I’ve ever known who has an attraction to startup environments does so because the surprises and opportunities are addictive. Knowing that things can change on a dime, that a large new client can change everything, or that a new product will open up all new markets, knowing that the person on your left is the entire sales team and the person on your right is the entire QA team means that some days you’re going to have to pitch in an help someone who does something different than you do just to make it through the day.

To be sure, people who like clear roles and responsibilities, defined priorities, clear-cut areas of expertise, and a regular, stable schedule that they can easily predict and painlessly plan around should avoid startups.

But in all my years of going from startup to startup to startup, the two kinds of people I have seen who thrive the most in highly chaotic, rapidly changing startup environments are:

1. People who bore easily, and who need a constant influx of stimuli to stay interested and engaged. These people are usually extremely smart and creative, and seek out environments that are unlikely to box them into anything too confining.
2. People who don’t know what they want to do. I most frequently see this among recent graduates who are not yet sure what career direction they want to take. They are often interested in a number of different things and are looking for a professional buffet they can sample from for a while before settling in on something specific for the long haul. This is often easy to maintain while you’re young, single and full of energy. But often this group settles into a discipline, gets a little older, starts a family and becomes a little less drawn to the chaos.

I fall into both camps. I started off in the second group: young, eager and entirely unclear what I wanted to be when I grew up. And then after doing it for a while, I discovered that was the type of environment that was providing me the level of stimulation and motivation I needed in order to really love going to work every day. And the times I’ve tried working in environments that did not meet that need all ended quickly, because no amount of cushy paycheck could make up for being bored out of my mind.

Of course, I’m not 27 anymore; 18 hour days take their toll more than they used to and I’ve got a husband who is most certainly not a workaholic and has this crazy expectation of actually seeing me from time to time. One could generally argue that I should have probably grown out of my addiction to the chaos by now.

Perhaps. But the fact remains that until I can find another type of environment that provides even a fraction of the array of opportunity, I’ll keep gravitating back to startups specifically for their chaos.

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Definition of “Command” from StrengthsFinder2.0:

Instinctively, you earnestly apply yourself to seeing things as they really are. You bring a practical, matter-of-fact, and unsentimental outlook to various discussions, projects, or planning meetings. It’s very likely that you seem willing to take chances. You frequently venture into unknown territory when that can make the difference between capturing first place and finishing in second or third place. By nature, you like advancing on your own. You enjoy defying the odds. You find limited satisfaction in pursuing the easiest, the most popular, or the accepted course of action. Driven by your talents, you approach most win-lose situations in a practical and realistic manner. When you are intent on being victorious, you automatically extinguish any sentimental feelings you have toward your rivals. Chances are good that you might enjoy assisting certain groups by sharing your innovative thoughts with them. Perhaps people rely on you to present more creative proposals or solutions than anyone else.

Strength #5, according to the assessment. This would be the heart of my allergy to the path of least resistance. It would also be the heart of my ability to avoid getting sentimental, even when most other people around me are.

This one is interesting to me, because it’s the one that I see other people respond to the most — even when I don’t realize I’m projecting it. It’s also the one that I least often recognize that I’m manifesting in the moment, until I see someone’s reaction.

On the other hand, again, I think this one is part of what has made me a good project manager. One of the weaknesses I often see in my vocation is a predisposition towards one discipline at the expense of the others — e.g. development, engineering, design, etc.

I see the success of a project manager as being critical to that objectivity, specifically to avoid being drawn into any political tug-of-wars between different teams. It was years into my career before I started realizing that I tend to walk that line more rigorously than many of my peers. I also suspect that walking that line is why there have been times when I’ve found my chosen profession to be highly taxing and frustrating.

My aversion to following the crowd definitely comes from this strength, though. My need to prove that I can do something on my own and my overwhelming need for it to stand out among my peers is rooted in this one.

This one is probably the one that gets me into the most trouble — because it can both get me in over my head and be highly off-putting to other people. But it’s also probably the one that’s opened the most doors that have led to the most fun — both personally and professionally. I think this one is largely where my innate ability to inspire confidence in others comes from. And that skill has served me better than most.

My other StrengthsFinder2.0 Results:

• Activator
• Strategic
• Significance
• Focus

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Definition of “Focus” from StrengthsFinder2.0:

Instinctively, you are industrious, diligent, and persistent. You naturally set difficult-to-reach goals. These normally demand a great amount of your time. While your work ethic is evident, you question whether the promotions, titles, opportunities, or status symbols you desire could exact too high a price. Driven by your talents, you typically immerse yourself in intense activities. Preferring a fast pace, you thrive on excitement. You appreciate being surrounded by like-minded individuals. They motivate you to expend even more energy accomplishing whatever needs to be done. You stay busy and work hard whenever it is necessary. It’s very likely that you have little difficulty giving intense effort to projects, problems, or opportunities that capture and keep your attention. Because of your strengths, you use your mental and physical energy for hours when the situation demands such effort. You generally persevere and push yourself to keep working on assignments until you finish them. You refuse to quit until you reach your goal. Chances are good that you sometimes improve your chances of reaching desired goals by making a list of them. Perhaps you progress more efficiently when you take time to attach a written explanation to each objective.

This is my #4 strength, according to StrengthsFinders2.0. According to my husband, though, it’s #1. This is the thing that always gets his attention the most.

Ironically, this is also the quality that I think has made me a good project manager in startup environments throughout my career. The fact that I thrive in precisely this type of environment is why I’ve never had any luck fitting into more structured, corporate environments.

Of course, the irony is that the first thing I do in a chaotic environment that demands this level of intensity is to work on ways to tame it enough to be a little bit less strenuously demanding. And, typically speaking, once I’ve been successful at that, the environment becomes innately less appealing and it’s time for me to move on.

That one may be a subject for a therapist.

My other StrengthsFinder2.0 Results:

• Activator
• Strategic
• Significance
• Command

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