Eventually I stopped fighting the inevitable, but I remain constantly aware of the fact that my husband and I have two very different relationships: one as spouses and one as business partners.  And there is no way to avoid the fact that there are times when the needs of one relationship create tension in the other.

A post on Forbes, When Siblings Don’t Pull Their Weight by Gene Marks, showcases an example of how one family business found a resolution to some of these challenges: a set of three siblings bought the family business from their parents, and eventually ran into a problem because one of them wasn’t pulling their weight.

The solution Gene discusses is rather clever, but it’s a long-term solution.  In my experience working with family-owned businesses, there are two common challenges that surface in situations like this:

Avoidance. This was, predictably, part of the pattern Gene discussed in his sibling example: the problem festered for quite a while before a solution was found, because no one wanted to rock the boat.  Everyone was afraid of upsetting their parents and generally causing family strife, so the two siblings who were carrying the heaviest burden of the business avoided saying anything for as long as they could stand.

Urgency. Often this becomes an issue because of avoidance — though it can also be a matter of size.  The longer you avoid a problem, the more likely it is that it will get worse until you have no choice but to deal with it.  And usually, by the time that happens, you’ve got a much bigger mess on your hands than you would have had if you’d handled it sooner.

Small businesses in particular are often cursed with tight enough living conditions that too big a crisis can quickly sink the entire ship.  One of my clients owns a business with his wife, and after a few years of growing it, they decided to bring her daughter in to help run the daily logistics.  The idea made sense for all concerned, and so they got started.

Unfortunately, over time, the daughter’s idea of “a full work day” did not jibe with her step-father’s.  Since the point of bringing her on-board was to off-load as much of the burden from the parent’s as possible, the fact that they were shelling out an enormous percentage of their revenue to pay her salary while not seeing any real reduction in the number of hours they were putting in started causing a problem.

It didn’t take long for my client to get very frustrated: his wife was responsible for managing her daughter, but she didn’t want to be the bad guy.  Unfortunately, she didn’t want her husband to do it, either.  Relationships all the way around quickly grew strained, until the point that family events were palably uncomfortable for everyone.  The situation went on for more than two years before outside circumstances intervened, and the daughter left the business of her own accord.

Now, while they still maintain the same workload as they always have, their financial burden has dropped by more than 20% since they no longer have to pay her salary.  In a small family business with extremely narrow operating margins, that 20% has been a huge relief.  But the real problem was avoided, instead of resolved.

Working with family presents a set of challenges over-and-above the normal assortment that comes standard in most small businesses.  Earlier this year at Austin’s South by Southwest Interactive conference, I asked Wine Library‘s Gary Vaynerchuck about his experience joining (and ultimately taking over) his family’s business.  My specific question was how they all got through it without hurting each other’s feelings.

His answer, of course, was that they didn’t.  He said they constantly hurt each other’s feeling in the beginning, and it took a long time to make work.  But the important thing was always to remember that, no matter how hard it was to integrate their different styles into a rational working relationship, they were family and they loved each other.  They wanted to work together, so they just kept trying until they got it to work.

The answer is different for every family.  Some businesses are too delicate to withstand the turmoil that comes with family strife; other businesses may be too delicate to withstand replacing a family member.  The only real key is to find a way to be honest and don’t fall into the avoidance trap.  It’s possible to be honest about difficult issues and still be kind.  But the longer you let something fester, the harder that becomes.

The old saying, “Bad news doesn’t get better with age” holds true here: if you keep something bottled up, eventually you’ll explode.  It’s bad enough to have a fight with someone you love.  But the last thing you want is to wait until it’s so bad that your business can’t bounce back.

So remember, bite the bullet, be honest and remember that they are your family.  Working together may not be the solution you had originally hoped for, but I guarantee, your holiday dinners will be much better if you don’t have to rely on the lawyers to intervene when it’s time to pass the cranberry sauce.

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

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.

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.

Tim hits the nail on the head right out of the gate: the absurdity of that recommendation is the idea that once a business is successful, it is somehow going to miraculously be easier for an entrepreneur to walk away from it to start building a life.  He gives a list of very useful things to do to avoid falling into this trap.

For me, though, the real problem with this advice is the assumption that it is only business that it hard — having a life is easy.  Anyone who says that has never tried to shift gears and go from being a workaholic to being a romantic partner.  As someone who has spent five years working on that transition, I’ll tell you: it’s much harder than it sounds.

If you spend your twenties — and worse yet, also your thirties — focusing on building your business while neglecting your life, why would anyone assume that suddenly starting to focus on having a life at 40 is going to be a cake walk?  There are days when I am convinced the reason we live so long is because that’s how long it takes to practice to even start getting our lives right.  If we don’t even begin until it’s half over, then we’re out of time before we begin.

One of my favorite bloggers, Penelope Trunk, writes about this regularly: as a serial entrepreneur, she moved her family from New York City to Madison, WI for their life.  She founded a tech startup in a city with virtual no tech industry because that was where it made sense for her family to live.  Has it been a struggle?  Sure.  Was there reasoning in her logic?  Absolutely.

Everyone wants to know that their legacy has an impact — for some people having kids is enough.  For others, leaving behind impressive business accomplishments is enough.  But if what you want is both, then you can’t delude yourself into thinking that you can ignore one for half your life and suddenly make up for it in the second half.  Time doesn’t work that way.

So many entrepreneurs I know start their own business because they want a lifestyle that allows them what working for someone else never has: opportunity and flexibility.  And most of the reasons they want those things are because they have, or want to have, a life.

I’m with Tim: waiting until your business is successful to start building a life is asking to have a lop-sided legacy.  And that may be fine for you, but make sure you know that going in.  In business these days we spend so much time discussing how hard it is to build the necessary relationships to be successful.  Does anyone really think it’s easier to build successful relationships in the rest of your life?

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

Associating: The ability to connect seemingly unrelated questions, problems or ideas from different fields.

Questioning: Innovators constantly ask questions that challenge the common wisdom. They ask “why?”, “why not?” and “what if?”

Observing: Discovery-driven executives scrutinize common phenomena, particularly the behavior of potential customers.

Experimenting: Innovative entrepreneurs actively try out new ideas by creating prototypes and launching pilots.

Networking: innovators go out of their way to meet people with different ideas and perspectives.

I find the results of this study interesting, if not earth-shatteringly shocking.  What’s even more interesting, however, is that CNN’s article also comes with some recommendations about how to develop those skills, even for those of us who don’t consider ourselves tremendous ‘innovators’ to begin with.

Recommendations:

• Teach yourself to think differently by deliberately taking opportunities to act differently
• Identify a problem and writing nothing but questions about it for 10 minutes a day for 30 days
• Identify a business, customer, supplier, or client, and spend a day or two watching how they work so you can better understand their issues
• Build a diverse network, and understand people’s backgrounds, interests and strengths; and then make sure to remain in touch with them regularly

Since most of us are creatures of habit (to one extent or another), taking opportunities to break behavioral patterns and act differently can be hard.  But it is the corollary to the old saying, “The definition of insanity is doing the same thing over and over again and expecting different results.”

So, sane or not, if you want different results, then make sure you do something different.

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

Family
Universally cited by women who get off the corporate ladder as the biggest reason to start their own businesses, opportunities for stay-at-home parents (mostly targeted at Moms, though also often applicable to Dads) are everywhere. Whether it’s Brazen Careerist founder, author and blogger, serial entrepreneur Penelope Trunk, Forbes magazine’s “Mompreneur,” Lisa Druxman, or dedicated online communities, such as Work-at-Home Moms, opportunities for parents to build a family-friendly business only continue to grow, as does their recognition as truly viable business models.

Geography
As someone who likes to pick up and move a couple of thousand miles away every couple of years, this is one of my biggest motivators: being able to work no matter where I am. In the age of the Internet, a laptop and an Internet connection are a mobile entrepreneur’s best friend. Author of the best selling book, The 4-Hour Workweek, Tim Ferriss, blogs about the his misadventures abroad, while communities like Location Independent offer advice to entrepreneurs building geo-neutral businesses.

Schedule
The single biggest complaint I hear from anyone who has ever worked for themselves and has then gone back to working for someone else is about the schedule: being told what hours to work, not having the luxury of picking your own routine and needing to account for your hours. Whether you are a night owl, a highly social power-networker or just someone who likes to be able to take an afternoon nap, having at least some measure of control over your daily schedule can make all the difference between enjoying your week or dreading it.

For most of us, I think it’s ultimately about time: we have limited time on this planet, limited time to do the things we want with the people we love, and limited time to see and explore all the experiences we want to take in. While there are definitely always times when being your own boss is more time-consuming than working for someone else, knowing that your work is going towards allowing you to have some measure of control over your time so that you can spend it on your priorities is often worth the sacrifice.

I know entrepreneurs who are motivated by a desire to spend time with their grandchildren, those who want to volunteer with their church, some who never want to have to wake up before noon and one (other than me!) who wants to be able to have time to water ski every single day. Whatever the reason, these entrepreneurs want a lifestyle first, and are willing to make the sacrifices necessary to support that goal.

So out of all the lifestyle reasons to be your own boss, which matters most to you?

There is Ross Dawson, who writes Trends in the Living Network, which I love because he addresses the juncture of technology, business and society in a way that is uniquely in-line with my interest in that intersection and no one else covers it in quite that same way.

Scott Ginsberg from HELLO, my name is BLOG is another one whose articles I always read because he breaks things down into bite size pieces (which makes implementing change so much easier), while operating from the basic premise that being approachable is a learnable skill, and just because someone may not be born that way, doesn’t mean they have to spend their life being considered unapproachable.

Eric Ries of Startup Lessons Learned writes one of the best blogs on entrepreneurship, and of course, there are a few others, such as MyVenturePad, which comes in handy for aggregating a ton of content from different places that makes it easy to sort through when I have the time to block off for it.

Umair Hague writes the Edge Economy on Harvard Business, which I love because his view of society and economics is one of the only ones I have found that recognizes that the Industrial Age is over, and that the rules of the Information Age are different.

But while all of those are good intellectual stimulus, there are two bloggers whose writing is far more personal, and who routinely manage to strike right to the heart of things, even if they don’t know it.

Penelope Trunk, Brazen Careerist
As a workaholic female ENTJ entrepreneur from the tech sector with a knack for being problematically honest who moved her family from NYC to the middle of the country for lifestyle reasons, I have met very few women I can truly relate to.  Penelope is just about the only one.

What I love most about Penelope is that she is every bit as blunt in real life, and you can’t predict what she’s going to say next.  She cuts straight through normal bullshit that people are used to just putting up with (like the fact that making Christmas a national holiday is divisive and inappropriate), doesn’t turn to jelly apologizing profusely when she offends someone (like her notorious miscarriage Tweet) and always manages to spark a realization just by being direct (like pointing out to me, when we met at SXSW in March, that I should be doing a better job of making sure that my network included people younger than me, not just older).

The even more valuable thing I get out of Penelope’s writing, though, is the fact that for some of us, work really is easier than a personal life.  Even once we have an actual life, it’s still easier to hide in work and neglect it, avoid it and pretend that it doesn’t make us crazy.  While I definitely don’t necessarily like or want many of the same things in life that she does (such as kids and living in a cold climate), she reminds me that I’m not as anomylous as I often feel for being a confident, successful Gen X professional who doesn’t take direction well and who is always going to find clients, conference calls and project timelins far easier to navigate than the messy interpersonal relationship stuff that comes with being married.

Joshua-Michele Ross, Opposable Planets
Josh is one of those people who comes into your life and who, from the moment you meet, is obviously and clearly a far more powerful, creative and interesting force than even he seems to understand.  I first met Josh almost ten years ago, and we worked together for nearly three years — the last one of which we shared an office.  As we all always knew was inevitable, Josh has continued to do very cool things, demonstrating his brilliance and being both insightful and motivating to the people who know him.  And, all the while, being ethically-centered, well-grounded and astoundingly humble.

It doesn’t matter whether he is doing video interviews of technology and business leaders, whether he is in front of the camera doing videos for Forbes, whether he is meeting with clients about their online strategy, or whether he is finding a new and particularly incisive turn of phrase to distill an amazingly complex thought into something readily digestable, what makes Josh most incredible is that he’s got the rarest of all possible talents: he makes the people he interacts with feel smarter, just by being around him.

While I know many people who have paid Josh many compliments over the years (both directly to him, and in the third person when he wasn’t around), over time, I think what they all boil down to is just that.  No one leaves a conversation with Josh feeling drained, stupid, patronized or diminished in any way.  That’s his strength.  You can’t help but like who you are and how you feel about yourself after you’ve spent time with Josh. (Even if that means, these days, that I only get to do that long-distance, via his blog.) And because of that, there is no one whose success I find more inevitable than his.

And they are both great reminders to me about how I know I can be better at a wide range of things.

Between getting settled into the new project and speaking to old friends at former companies (some of whom are now unemployed, while others only wished they were), I’ve been thinking about a number of things that seem to have dovetailed together in a way I wasn’t expecting.

First and foremost is career management. Long a favorite topic of mine, what I’ve been thinking of recently is how sadly common it is for a boss to be totally useless when it comes to helping their employees with career management plans. More than a few of them don’t think it’s part of their responsibility (which I find inexcusably lazy), but even more of them seem to simply not think of it.

This got me thinking of the series I wrote at Christmas, “A Christmas Card to My Bosses: Thanks to Three Very Wise Men.” While I wrote blog posts on the great lessons I learned from each John, Robert and Dave, the thing that I didn’t state explicitly (but which was implicit) was that each of them cared about and was focused on making sure the people on their staff were getting the career development support, encouragement and pushing that they needed. They were all acutely aware of the role they played in developing their people; they took that responsibility seriously and they executed against that.

I see so many talented people who do not have that. And when they finally have someone actually demonstrate some interest and some focus on helping them define and reach their career objectives, they are often so stunned they can hardly believe it.

Why is it so hard? Most people who have been successful enough to be the boss have accomplished that because they know how to manage their own career, so why is it so hard for them to help give guidance and advice to someone else on how to do the same? It shouldn’t be — and I don’t buy that it usually is. I think the reason most people don’t do it is because they don’t make time to do it.

An important thing to keep in mind: statistically speaking, most people do not leave their job, they leave their boss. So are you doing what you need to do to keep your employees engaged and supported so that they stick around? If not, why not?

So that’s my challenge to bosses everywhere: have you worked with each of your direct reports to make sure you understand their career goals (at least as much as they do)? Have you worked on a plan for them that will help them make progress towards those goals? Are you checking in with them regularly to make sure that they are staying focused on at least some of the accomplishments they need in order to stay on track?

Part of being a leader is helping make sure the people you are leading are getting where they need to go. If you aren’t doing that, then where are you leading them?

And then I got a job — that ultimately turned into a career — at a start-up. Pay dirt!

The transformation that sparked in me is still an endless source of amusement among my friends. It took me a while to realize why, but eventually it was clear: the problem with school is that there was an upper limit on what I was capable of achieving. It was an artificial cap on how well I could be scored. I found that inherently disincentivizing. In business, however, there is no upper limit. You can take something as far or as high as you can push it (given the right environment, of course).

And, even better, in a scrappy, entrepreneurial, risk-taking startup (especially one trying to survive an economic downturn) someone who is hungry, talented, teachable and willing to dive into the deep end of the pool head first has tremendous opportunity for growth. The first three years of my career were the most educational, exciting and energizing time of my life — all of my years of school combined couldn’t compare to those three years. Everything was new, everything was interesting and I never once had the slightest bit of doubt that I could conquer anything that came my way.

Ah, the hubris of youth!

Of course, there were downsides. Like many young people, I didn’t know my limits and was constantly pushing the envelope in ways that I probably shouldn’t have (and in ways that I’ve since learned not to do). Whereas many 26-year-olds may be more inclined to do that with parties, I did it with work. I ended up missing a lot of important events in the lives of friends and family because of that.

I was also still extremely idealistic about a great many things. Instead of The Pragmatic Contextualist, an appropriate blog title would have been something along the lines of The Snarky Idealist or Bring it On and Get Out of the Way! (Which, ironically, is still how some people tend to view me, though I have toned down considerably with age.)

But that idealism was invaluable to me, because it made me fearless: if anything is possible and I’m extremely capable, then what do I have to be afraid of? I don’t tend to be very risk-adverse in general, but I have become more cautious with age (though, not quite enough for either my husband or father’s tastes). Back then, though, it would never occur to me that I wouldn’t figure out a way to succeed at whatever I did — which meant I was a hopeless volunteer junkie.

My biggest rush came from fixing problems, and in a post-bubble burst start-up, there were plenty of things to be fixed. So I had an endless supply of opportunity, and endless confidence in my own success. Happily, I also had bosses who went from having nothing to lose by letting me try, to truly believing in my ability to make a positive difference.

As was inevitable, a few kicks in the teeth later, and I stopped being quite so cocky. The pragmatist in me was ultimately born of those experiences, and the eternal idealist retreated to the back, only to come out for the occasional political event.

One of the biggest, most valuable lessons I learned was how to deal with chaos. More recently in my career, I had a bizarre moment when a senior IT Director — who was easily 25 years older than me — groused that we were working in “the most chaotic environment” he’d ever experienced in his life.

I wanted to laugh and call him a weenie (I restrained myself — though barely). The environment we were working in at the time was easily the least chaotic environment I’d ever experienced, and his inability to roll with the punches made him a particularly weak and frustrating leader in my opinion, because he got frazzled very easily, whined constantly and was tremendously rigid. It never occurred to me until that moment that my ability to handle chaos was all that unique.

Naturally, one of the dangers of getting a bit too used to high volumes of chaos is that you can become a drama junkie. This did happen to me, and it took me a while (and outside circumstances) to curb it. But what I have seen of most drama junkies (and trust me, I wasn’t the only one I knew) is that, the older we get, the less tolerance we have for that same constant fever-pitch of insanity.

This is another reason that I have often recommended aimless twentysomethings seeking career advice to explore startups: because by the time people are settled in their career, married or have kids, startups can be a bit too rough on the lifestyle. So if you’re going to do them, best give them a shot while you’re young, energetic, single and have as few external obligations as possible.

But when I look back on that time now, I am profoundly grateful. I was drinking from a fire hose, and it never occurred to me there was any other way to work. I got to sample a spectrum of potential opportunities and figure out which ones held some appeal, and which ones didn’t. If I had found myself in a more stable, structured environment back then, I can’t imagine where I’d be now, because the lessons I learned there, and the all-you-can-eat-buffet of opportunities that I had available to me at the time are how I found my way into a career.

In the scheme of things, I look back on the most pivotal, impactful decisions of my life and the day I left the famed O’Reilly Publishing — which is where I thought I’d wanted to work for years — and went to MarketLive (at the time it was still called MultimediaLive) was one of them. And since then, I have found myself encouraging twentysomethings who do not know what they want out of a career to look at startups, because as long as they can develop a bit of tolerance for chaos (which I firmly believe everyone should do), they’ll usually find opportunities they never knew existed.

What do you think? Are startups a good or bad place to start out your career?

Specifically, I’ve been thinking about how early career choices can really set the stage for the directions we take in life. As is often the case, many of the largest influences on our lives are not obvious until many years later. And while I am as likely as anyone to take them for granted, every once in a while something will happen to make me stop and consider the series of events that brought me to where I am now, and what the unintended consquences of seemingly small actions or events have ultimately provided.

There were three defining elements of my early career that I have been noodling on, because they had much larger impacts on me than I ever would have predicted at the time:

• Getting your start in a startup. What is the value to launching a career in a startup environment?
• Being in the ‘wild west’ of a new market space. What does it mean to be in a new space?
• Transforming a company from being “a services company” to “a product company.” What are the differences and why are they important?

Undoubtedly, the first two of those are a bit sexier than the third. However, all three ultimately shaped me in ways I never fully realized at the time. The lessons learned were a bit rough sometimes, but when I compare some of my experience to that of my peers, I realize that I had the opportunity to be involved in some things that have served me extremely well and that I wouldn’t trade in for anything.

Over the next couple of days, I’ll cover each of these topics in a separate post (each one is too long to combine them).