One of the biggest assumptions I make is that the only real learning — in both life and business — is attained by doing. And usually doing is a constant experiment. Do, make a mistake, re-do, and repeat as needed.

But what about people who actually do learn in a more academic way? People who want and need to first read, then discuss, then process, then internalize and then try? And is it possible to be successful in life — and especially in your own business — if that’s the process you need to go through to learn?

That’s a perfectly fine solution for a 19-year-old, just getting started, who is still in school. But what about a mid-life professional in a career change, or launching a new venture? What do they do? If you’re trying to get a new business off the ground, you don’t get the luxury of pulling to the side of the road and going back to school for a couple of years.

For some of us, that’s ok. In fact, for some of us, that’s fabulous. But for others, it’s overwhelming, upsetting, frightening and debilitating. What is their solution?

The only thing I can think of is finding a mentor. But how does someone who needs an immersive learning experience find a full-time mentor to come into their new business for 3-6 months, and walk with them as they learn to navigate the treacherous world of a startup? Is it possible? And how does an unfunded startup compensate for that?

I’m genuinely curious and truly want to know how to blend a more traditional academic learning aptitude with the daily chaos of a startup business venture. The two feel mutually exclusive to me, but I feel confident that it can’t be an entirely unique problem, either. Someone somewhere must have solved it. But who? And where are they? And what did they do?

Of course, part of the reason that I find this decade’s list so interesting is because almost every company listed has touched my life — some more directly than others.  And, quite rightly, most of the entrepreneur’s Inc. calls out have created brands whose influence has become deeply baked into our culture in ways we never would have predicted in 2000, but which we take for granted today.

1. Steve Jobs of Apple
2. Jeff Bezos of Amazon
3. Jack Ma of Alibaba.com
4. Martha Stewart
5. John Mackey of Whole Foods
6. Leslie Blodgett of Bare Escentuals
7. Marc Benioff of Salesforce.com
8. Mark Zuckerberg of Facebook
9. Tony Hsieh of Zappos
10. Peter Theil of PayPal
11. Reed Hastings of Netflix
12. David Neeleman of JetBlue
13. Nick Denton of Gawker Media
14. Stefan Persson of H&M
15. Evan Williams and Biz Stone of Twitter
16. Nandan Nilekani of Infosys Technologies
17. Larry Page and Sergey Brin of Google

Aside from some of the more obvious companies that made this list — e.g. PayPal, Google, Twitter, Facebook, Apple and Amazon — part of what I love about this list are the non-tech companies that make an appearance: Whole Foods, Bare Escentuals, JetBlue and H&M.

Coming from a tech-centric background, it’s often easy to forget that “innovation” is not synonomous with “technology.”  I think this is something that is often forgotten, particularly when it comes to startups.  The focus is often put on technology, instead of on creating innovative solutions.

Zappos and Netflix are two of my favorite examples, because they are often lumped into the category of “tech companies,” yet in reality, their true market differentiator has almost nothing to do with the actual technology itself.  The technology they use — in both cases ecommerce, and in Netflix case especially, a super-heavy dose of social commerce — is a means to an end, but their real innovation is around service.  Because, let’s face it, there is nothing about either of their core business that is new: Zappos sells apparel items and Netflix rents movies.

Yet in a world where apparel distributors are operating on razor-thin margins while eating enormous costs in real estate and related overhead, Zappos stands out as a customer service example to etailers everywhere.  And while Blockbuster is closing down stores by the hundreds and the movie studios scream about online piracy problems, Netflix continues to demonstrate that there really is money to be made in renting movies. (And we will skip the extent to which both companies continue to be examples of great business cultures with enviable employee engagement levels.)

The greatest thing about this list, though, is how much of it represents massive change to the small business arena itself.  Apple, Amazon, Salesforce, PayPal, Twitter and Google have all been phenomenally disruptive influences that have helped set the stage for the new era of small business opportunity.  Whether they all started out with that intent or not, each of them has helped build a new set of business models and standards that foster more opportunities for small business success.

At what prior point in history would a list like this have included so many amazing influences that have helped entrepreneurs have access to more tools and services, and help make them more successful?  None, really.  So the real reason I love this list is because it continues to show that, even the biggest success stories we can find, are successful because, in large part, they are continuing to fan the flames of entrepreneurship far beyond their own front doors.

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

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.

The single biggest issue I find when I come into an organization to help get things back on-track, is that when leaders are entirely pre-occupied with a strategic vision, there is a tendency to ignore employee development and management activities.

The irony, of course, is that a good strategist understands that employees are the key to making their strategic vision come to life. Yet time and time again, I have found that groups with the most strategically-focused leaders are the ones where the employees are the most neglected.

The problem, I believe, is in the misalignment of how a leader identifies — and what they actually like to do — versus what is part of the responsibility of the role. How many people who consider themselves innovators, visionaries and strategists are placed in the role of manager? And, honestly, much about managing people is terribly “innovative”? Very little of it. Managing people is down-n-dirty work.

Someone who manages people has to deal with messy details like:

• team members who don’t get along
• people who are not living up to expectations
• talented people who are bored thanks to being under utilized
• political entanglements with other departments
• hiring freezes that prevent backfilling vacated positions
• low morale among teams
• budgetary constraints that prevent a manager from paying an employee what they are truly worth
• helping form a career development plan so team members don’t stagnate
• being honest with a staff member when there is no future for them with the organization

Face it, none of that is sexy. But someone who can’t or won’t do those things is not someone who should be managing people. And yet it happens all the time: a strategically oriented leader is put in the role of a manager, because leadership likes the idea of having a strong strategic direction developed for the department.

Nothing wrong with that. Of course the best departments are marching towards a strategic vision. But if you don’t take care of your team in the process, who exactly is doing the marching?

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?

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).