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.)

The report goes on to highlight that over the past six months that TARP recipients have been required to report their lending activity, “the banks have cut their collective small business lending by 4%.”

It’s impossible not to recall WorkingPoint CEO Tate Holt’s recent blog articles entitled, “Main Street vs. Wall Street,” in which he asked the question, “Rather than making it easier for banks to access funds, why not make it easier for small business owners to access funds?”

It sounds a lot like the “too big to fail” argument, doesn’t it? At best, it’s extreme and reckless hubris. Small business employs 52% of the American workforce, and is routinely responsible for providing the majority of new jobs generated in this country. And yet 3 of the 22 financial institutions that got TARP money do not provide loans to small businesses at all, while the other 19 continue to cut back.

Entrepreneurs are a profoundly important element to our economic recovery. While the large financial institutions continue to try to mitigate their risk by denying small business loans, there are a few things that small businesses can do to help ride out the credit crunch:

1. Use a community bank. (Kelli recently discussed this in her WorkingPoint blog post titled, Managing Your Cash (Pt. 3).) Just like in your small business, a community bank is owned and operated by local people who understand local needs, trends and conditions. Building a relationship with your community banker is the best way to help build in some insurance for yourself, because local banks make decisions locally, instead of across the country where no one knows you, your business or your reputation. If you need an idea of where to start, CNNMoney.com has a list of banks by metro area that have recently made SBA loans.
2. Find (or form) a local entrepreneur or small business network. Networks of entrepreneurs can often help share resources, collectively negotiate rates for goods or services, and offer creative problem solving solutions that you’ve never previously considered. Think of it as local, small-scale crowdsourcing of ideas and services.

Other possibilities to consider:

• Do you have a local college through which you can bring on interns to help supplement your staff or work on special projects? College interns can often help with a lot of the areas outside of your core business functions, such as marketing, advertising, website design and development, etc.
• Have you considered the myraid of online crowdsourcing opportunities? Crowdsourcing is a powerful way to parse out discreet tasks, especially those that you need to get done quickly, but for which you do not have the in-house talent to manage yourself.
• Do you need to rent your own office space, or do you have local co-working facilities or sublet spaces that might be more affordable? Obviously not all businesses can share space, but far more can than do. Is yours one of them?
• Do you have a network of other entrepreneurs with whom you can partner to bid on larger opportunities than you would normally be able to support alone? A couple of bigger clients can make the difference during a downtime; and businesses that do not have the contacts or the requisite formal relationships to get a foot in the door can still partner with someone else to have access to some great opportunities.
• Have you gone back to your existing vendors and attempted to renegotiate your current rates? Everything from your cell phone provider, to the interest rates on your credit card are potentially re-negotiable if you continue to be persistent.
• Do you have a local adult or community education program through which you can teach a course? Often times, this is not only a great opportunity to help supplement your income (a little bit, anyway), but it’s a great marketing opportunity, since community education providers see an increase in attendees when the economy is down.

Finally, get creative. Obviously there are some things for which cash is essential, and there is simply no way around that. But there are a lot of things that may come with more options than you’ve previously considered.

(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?

The “interesting” conversation I had afterward was because one of the attendees (in a private conversation) busted me for never once using the word “Agile” in my presentation. I’ve told him that it was deliberate, and here’s why:

What’s in a Name?

“Agile Development” is bullshit in and of itself. I don’t like or use this phrase because it’s a dangerous misnomer. As I’ve written about before, either your entire organization is going to be “Agile” or none of it is. You can’t just have “Agile Development” and expect that Project Management, Design, Testing and everything else won’t be impacted. The trouble is that Agile is all too often discussed, described, evaluated and generally understood as it applies to development only, leaving other aspects of the project lifecycle out in the cold.

The Methodology Myth

I have been in startup development environments for my entire career. And if there is one concrete, immutable fact I have learned it is that no startup environment is mature or stable enough to completely adopt and implement any pure methodology within any discipline — not requirements, not development, not project management, not testing. It simply does not happen — nor should it. While most development environments will dabble with some aspects of Agile, the fact is that — like all process — it is typically really a hybrid between a couple of different approaches, in combination with some home grown goodies, that is all tossed together to come up with something that fits the organization. Any other approach is folly.

You Say Potato, I Say Potaaaaaaaaaaaaato

One of the problems that has evolved over the years when it comes to Agile is at the heart of it’s value. As a methodology, Agile is specifically about results more than form or procedure. As an execution-oriented person in startup environments, I praise the focus on results. However, as a project manager, I also have to say that I have seen far, far too many developers use the methodology as an excuse for being lazy and sloppy about writing documentation. I used to debate with one of the Development Managers/Architects at JetBlue all the time: he was a huge advocate of adopting Agile methodologies, and I would always tell him that he needed to be careful of the language he used, unless he wanted to see a backlash from project and functional managers who’d been burned by this in the past.

He Said, She Said

Another problem with the language we use to describe Agile (in combination with the myth that it is or should be a dev-only consideration) is that, grammatically speaking, the word agile and the name Agile are often used interchangeably, even though they are not identical. This is particularly problematic when it comes to non-tech executives who hear “agile development” and think that means they are just going to get their project executed more quickly. All too often, I’ve seen Agile evangelists “sell” leadership teams on the idea that Agile is the way to go, without ever really explaining (in business-speak) what that means, what that will take and why it is of value. Even worse, most of the time, those evangelists actually think they really did explain it well.

Pragmatic Agnosticism

In the end, however, my biggest reason for not including the word “Agile” in my presentation is because, when it comes specifically to the core project management disciplines of communication, documentation, change management and entry/exit criteria, methodology agnosticism is key. This is never more true than in a startup where things are guaranteed to change before you have your Gantt Charts unpacked. Some of the tactical details may be different — whether it’s roles and responsibilities, sequence of events, etc. — the the underlying tenets are the same. And any project manager who says that communication, documentation and change management are fundamentally different in an Agile environment vs. a Waterfall environment are blowing smoke.

In the end, project management is a disciplined centered around the concept of integration. And integration is about effectively combining the efforts and products of multiple different disciplines into a final product of value. That can’t happen without communication, which includes at least some degree of written artifact (often around entry/exit criteria), and managing the inevitabilities of change. So, in a 45-minute presentation, it made more sense to me to skip over the great and eternal methodology debate, and move straight on to the basics that universally apply, regardless of what approach a team is taking to getting the work done.

I’m not entirely sure that the person I was speaking with agreed with my approach. And, in hindsight, I should have taken a moment at the beginning to state that I was going to be speaking from a methodology neutral standpoint. Definitely my over-sight there. I’ll be more conscientious of that in the future.

But people who want to get religious about a methodology can espouse whatever they like, but in the end, you have to be pragmatic in order to deliver a project (much less a recurring series of projects). And zealotry is never pragmatic.

When the bubble burst back in 2000 it was because speculation had driven realistic performance expectations, sanity and reason out the window (keep throwing endless piles of money at most people, and eventually most of us will get stupid). The industry itself, as well as those watching and investing in it, had bought into its own hype, and then it was crushed under the weight of it’s own hubris and lunacy. (Not unlike what is currently happening to the financial services industry.) Critical lesson: watch the hype and don’t drink the KoolAid. (A caution I would also issue to the current level of hysteria going on in the social media space.)

What this meant, of course, was that companies that had not yet become profitable or did not yet have a self-sustaining business model were S.O.L. VC money evaporated over night. Gone were the massages and catered lunches and lavish holiday parties. Suddenly we were awash in pay cuts, layoffs and absorbing the workloads of people who’d left because we couldn’t afford to replace them.

We were lucky. At that point, we were still a services company (though we were working on our product; it just wasn’t done yet), and that bought us a little bit of time. Not a lot, but — as it turned out — enough. And we sold our asses off. Everything we did for clients was billable. Everything was custom. Everything was a one-off.

Naturally, this presented problems in the scheme of things, because while this was providing us with live-saving revenue, this was not at all scalable. And our leadership knew it. So we continued to push forward with our plans to transition into being a product-based business that offered additional, ancillary services.

The troubles here were strategy, communications, education and execution. For those of us who were living on the services side, we had a culture that was services-centric — not product-centric, and there is a huge difference. In a services-centric culture, your answer to clients is always “yes.” And clients expect your answer to always be “yes.” It never occurs to either of you that the answer could or should be anything else. There is a culture of expectation that must be transitioned, and it must be done thoughtfully and carefully in order to avoid alienating the very people who are keeping you in business.

Now, to be sure, you aren’t going to have a business if you get in the habit of saying “no” to your customers, but there is a big difference between being an order-taking organization whose response to “Jump!” is always, “How high?” and an organization that provides expertise and consultation to customers, as suppliments to a core product offering. The culture, the relationship, the value brought to the table are all very different. And shifting from one to the other is a significant change that needs to be managed carefully in order to keep both your staff and your clients onboard.

Furthermore, our problem was compounded by the fact that the product team was very insulated from the rest of the business. That include socially. They literally sat in a different building. The two groups barely knew each other, so not only did both sides feel misunderstood and taken for granted, but we did not have the opportunity to really find any solid common ground. The services teams thought the product teams were snobs; and the product teams thought the services teams were cowboys. And we were probably all at least a little bit right. But what we weren’t seeing is that each group had a different mission, and that we were each very much in-line with what we needed to be doing at that time.

What we didn’t do was actively execute against a long-term strategy to bring both teams in-line with each other. To whatever degree that did ultimately happen, it was more by brute force of circumstance than by much in the way of active planning or cultivation. Looking back now, so many of the conflicts, headaches, and missteps are painfully clear. And, since hindsight is 20/20, I see so many opportunities that were missed, that would have made all the difference — both when it came to the internal culture, as well as in our relationships with clients.

Of course, looking back, I also now realize that this was one of the early seeds that sparked my interest in change management. This was a big change that had do-or-die implications for the business. The sense of urgency and relevance needed to be truly understood by the services team to get their buy-in, and it simply wasn’t. Without that comprehension, managing client expectations was an endless series of bungled missteps that were constantly needing to be corrected. The services teams needed a roadmap; and we didn’t even have a compass.

Another reason that I love startups is that, given enough time, I know that I’ll have the opportunity to tackle this type of problem again, and be able to apply some of the hard-won lessons from last time to doing it better.