Have you ever found yourself doing something mundane where your mind had time to wander and for a split second thought, Wait. This isn’t right. This is not how my life is supposed to be. What am I doing?

There’s a scene in Seinfeld where George and Jerry have this “who are we?” moment. It starts at 1:55 of the video below if you want to jump to it:

Their moment is a bit more light-hearted than most peoples’. Truthfully, I think all of us have felt like this at some point in our life, and it’s not a pleasant feeling at all, which is why we do our best to shove it down as much as possible. Far, far too many people spend the majority of their lives trying to avoid admitting to themselves the extent of the disparity between what their life is and what they wish it was. As Thoreau said, “The mass of men lead lives of quiet desperation.”

Side note: If this is not you (and it may very well not be), then this post is not for you. But be aware that most people are unwilling to admit that they fall into this category. Be honest with yourself.

This is the part of the post where I start talking about motivation and making your dreams come true and blah, blah, blah. You’ve heard it all before. At the end of the day, the only thing you can ask yourself is why not?

• Why not quit your job and travel the world?
• Why not go back to school to get that degree that you dreamed of?
• Why not allow yourself to be vulnerable and ask that crush out?
• Why not risk everything to start that business you’ve always dreamed of having?
• Why not be brave enough to share your art with others?

I can give the answers to every one of these, and they’re based on simple odds. The truth is that the odds are against you. You will probably fail. Traveling will likely not be as romantic as you think and the financial burden of not having a job will probably make it worse. That degree will probably not be as interesting or as helpful as you think. The crush will probably turn you down. The business you start will most likely fail. The sad reality is that your art is probably not very good and most people won’t like it. Most things that you try at, you will fail at. If not, you’re not stretching yourself very far.

But why not try? The truth about failure is that it hurts. Badly. But it also makes you realize something: it usually doesn’t hurt as bad as you thought it would. You can start another business, ask another crush out, paint another picture. All is not lost. And hopefully you learned a few things the last time around. If you never try, you know where you’ll be in a decade? Right where you are now. Right where you are now. Look back a year. Five years. Ten years. Did you think this would be it? Did you think your life would look like this?

Why not just do it? Right now.

Why not?

Look back over the last week, the last month, the last year, and ask yourself this question: did I accomplish what I thought I would? Am I happy about the progress I made during that time? Am I likely to accomplish what I think I will over the next week, month, or year?

Truthfully, I can’t say that I’m unhappy about the progress I made over the last year, but it’s definitely less than what I had hoped for. I tend to look forward a year and imagine that things will have changed much more than they have. I imagine that my progress towards various goals will be much more substantial, that my life will look more different than it inevitably does, that I’ll have changed more than I have. Why? Well, probably because I’m an optimist. But also because change is hard.

There’s nothing really profound in this post, just some lessons that I need to remind myself of on occasion. Earlier this evening, I was sitting at dinner, pondering some conversations I had today about opportunities in the real estate market. The real estate market has taken a beating, and right now is a fantastic time to buy if you can make the deals happen. But financing those deals is hard, lenders are wary, and cash is scarce. On top of that, the general feeling in the real estate market right now is one of fear and dejection. The vast majority of people (even experienced investors) would conclude that this is a good time to sit on the sidelines for a bit and wait for sanity to return. But I wonder if times like these separate the timid from the titans. I spent some time today on the phone with lenders and people who are out there doing deals, and I’m much, much further along than I was at the beginning of the day, though perhaps still a long way from doing any deals. But the thing I realized tonight is that lack of capital, connections, experience, etc, etc. are not what’s holding me back. The only thing holding me back is me. The only thing keeping me from diving in 100% and making something happen is my unwillingness to do so, for whatever reason. Sure, lack of capital, connections, experience or whatever else will slow me down and make it that much harder. But it definitely can be done. I just have to want it badly enough.

As I think about what’s truly and honestly holding me back, I’m reminded of a quote:

“After a lifetime of making money and observing better men and women than I fall by the wayside, I am convinced that fear of failing in the eyes of the world is the single biggest impediment to amassing wealth.”
-Felix Dennis

What’s holding you back?

Ok, this video is old, but it’s a good reminder of some important lessons that are to be kept in mind if you want to start a company in this economic climate. If you thought it would be easy, you were wrong. If you thought you could ignore things like revenue, profit, and customer service, you were wrong. If you thought you could cash out for millions in a year, you were wrong. Entrepreneurship isn’t about the quick and easy road to riches. It’s about building something that has value, being in control of your destiny, and hopefully being rewarded for your hard work. If that’s what you’re after, this is a great time to start a company. If not, better hang on to your day job.

Don’t worry though…the next bubble is probably just around the corner

With the economy in shambles and the outlook for the next couple years looking pretty bleak, is now a good time to leave your safe job to start something of your own?

It depends.

VCs and angel investors are telling their portfolio companies to batten down the hatches and prepare for the worst, which doesn’t bode well. Money is going to be very tight and every company out there is going to have to do some serious belt-tightening. Getting investment is going to be even tougher. Exits are going to be extremely difficult and rare for awhile. We’re going to see layoffs, consolidation, and lots of bankruptcies as companies are not able to raise the cash they need to grow or sustain operations. It’s going to be very ugly.

That being said, downturns can be a great time to start a company, depending on the type of company you want to start. If you want to start something that’s focused on getting lots of eyeballs on the back of millions in venture funding, with little thought of profitability, now might not be the best time. On the other hand, if you’re starting something that truly adds value, has a clear revenue model, and helps individuals or companies be more efficient, then perhaps now is a great time. The key is going to be keeping things lean and understanding that the odds of a fast exit for untold millions just got a lot slimmer.

One practical note: throw a touch of realism into your plans. If you’ve got a great job with good benefits and no savings, now might not be the best time, especially if you have a family to support. Take the next six to twelve months, build up some reserves, build your company on the side, and then strike out on your own if it’s working. It’s very, very difficult to build a startup on the side (I speak from experience), but you don’t want to get into a situation where you quit, it doesn’t work out, and you’re homeless because you didn’t have a safety net and there are no jobs available. Think ahead and think defensively.

Tighten your belt, put your head down, and just keep trudging towards the goal of adding value at maximum efficiency. It’ll pay off eventually.

Well, I can’t believe it, but we’ve soft-launched BlueSwarm.com. We’ve been working on this project for a few months now and we’re proud to finally have something that the general public can play with. This is still a relatively early beta, but it’s functional! So what is it? BlueSwarm allows you to track your brand through online social media all in one place. With BlueSwarm you can see what people are saying about your brand on Twitter and blogs (many more services to come) all in one place.

Not only does BlueSwarm collect that information and display it in one easy to use location, we also do sentiment analysis and calculate an authority/popularity score (called a buzz score) for both the author and the item. This way you can see what’s important to you. You can sort by positive or negative items, by how popular the item is or by how much buzz the item has. That way you can get to the information that matters to you most, quickly and easily.

Once you have a chance to see what people are saying about your brand, you’ll want to be able to easily respond to these items to keep the conversation going. BlueSwarm makes it easy to flag items for later follow up or to respond to them via twitter without having to leave the site (and we’re going to be adding even more ways to respond soon).

This is just the start. We will be adding more services in the next few weeks, more ways to respond, display and interact with the data, as well as more ways to collaborate and share that data. We hope that you find BlueSwarm useful, please don’t hesitate to contact me directly or anyone else on the BlueSwarm team if you have any questions, feature requests or bug reports.

When I first heard that Yammer (the “twitter for business” startup) had won TechCrunch50, I had mixed feelings. On the one hand, I’ve been using Backpack’s Journal feature to do something similar with an agency that I do work with, and I immediately saw the value. It’s interesting to see what other developers or designers are up to. For a freelancer, Twitter itself is almost like working in an office, and I can see the value of doing something like a mini-twitter just within your organization.

On the other hand, it doesn’t seem that innovative or impressive from a technology standpoint, just a slightly modified take on a concept that’s been around for awhile.

But then I heard about Yammer’s business model. I’m sure this is a big part of why Yammer won, because it’s brilliant. Basically, users sign up to this thing using their corporate email address, which makes sense since they’re using it for work. It’s completely free for any employee to sign up, and they can do so without the knowledge or blessing of their employer. However, if the company wants to “claim their network” and have administrative control over the user account that their employees have, they have to pay $1 / month / account.

Here’s why this is brilliant: in a typical corporate environment, tools and services are imposed in a top-down fashion, and then HR spends tons of effort trying to get people to use them. I used to work at CNET, and we had this terrible internal productivity tracking tool that everyone was supposed to use. The interface was awful, the integration was terrible, and probably cost CNET a ton to use the service for thousands of employees. But it would have been worth it if it actually increased productivity by 1/10th of a percentage point, or allowed CNET to ferret out their most productive employees. But I doubt that it did, because the person using the system and person gaining value from the system were not the same person. Employees didn’t get much extra out of it, and largely saw it as what it was: more work so that management could keep an eye on them. All the value was to the organization, not the users.

Contrast that with Yammer. A couple people from CNET sign up, they want to see what their colleagues are doing at work, so they invite them. Some of those people sign up, invite more people, and so on. Pretty soon, hundreds of people at CNET are using Yammer to share what they’re working on, ask questions, etc. Then the organization finds out that there’s all this value locked up in Yammer, and they can pay a measly $12 / year for each employee to access that value. Think they’ll be willing to do so? You bet.

The problem with many enterprise tools is that the organization is the primary customer, and then they have to push their employees to use the tool, because the employees view it as just more work. But the brilliance of Yammer is that they’ve built a tool that infiltrates value into an organization, then charges the organization if they want to unlock that value. If you hit the users first and add value and then layer on features that the business wants, you’ve got an irresistible combination. Employees will sign up and use it on their own, without any prompting or cajoling from the organization, and the business will find that it needs to pay up to unlock all the value that employees are naturally creating because they want to. It’s a classic bottom-up strategy, and one that I’ve started to think about for some of my own entrepreneurial pursuits.

In August of 2007, I quit my job as a product manager at CNET Networks and started freelancing full-time. I do mostly web development and social media consulting, and I’m really enjoying it. I thought I’d share a few of the lessons that I’ve learned along the way.

1. Working at home sucks

Maybe it would work if I was always working at home by myself, had a separate room that was just for work, and had everything setup just so. Maybe. But I find that being at home has too many distractions, from TV, to my wife, to our new puppies. I get 2x - 4x as much done at my office as I do at home. What that means in practical terms is that paying a few hundred bucks a month for a small office or co-working space is well worth the price. Even a coffee shop is usually an improvement for me over being at home.

2. Working from anywhere you want rocks

On the other hand, having the freedom to work from home, or a coffee shop, or the beach on a tropical island, is one of the best things about working for yourself, especially in the line of work that I do. My wife and I have travelled a lot over the last year, something we never could have done if we were holding down jobs.

3. Everything takes longer than expected

From finding new clients to signing contracts to finishing projects to getting paid, everything seems to take longer than you expect. I guess this is because I’m an optimist by nature, but it’s something I’ve definitely had to adjust to. My advice: make sure you always have a decent reserve of time, money, and goodwill. You’ll probably need them.

4. Process is important

I guess this isn’t limited to freelancers, but I’ve just realized how important it is. When you do development work, you find yourself doing the same types of things over and over. I find it hard to force myself to take longer the first or second or third time around to setup shortcuts and process enhancements that will enable me to do it faster in the future, but it’s definitely worth it. If you find yourself cutting and pasting the same piece of code, then making a bunch of adjustments to change minor details, consider making it a class or a library that’s more flexible. Organize, optimize, and review your processes regularly. It takes more time now, but it saves a lot of time in the long run.

5. Small gigs > large gigs

All else being equal, smaller jobs are far better than large ones, in my opinion. It’s the same reason that small entrepreneurial projects are better than large ones: they tend to get finished on time and under budget much more often. Large projects have more room for error, ambiguity, scope creep, and miscommunication. Additionally, I find that I get fatigued when working on projects that stretch on for weeks or months. It becomes more of a struggle to get excited about working on the same thing yet again, whereas for a small project, you can maintain your interest and excitement through most or all of the project. The best project is one that you can knock out in a day or two.

I’d say that the one thing I have learned is that if you’re doing a large project, break it into phases and try to think of them as discrete mini-projects in themselves. But small projects are still better.

6. This is a stepping stone for me

I never intended to stick with contract work long-term, and the last year has just reinforced that in my mind. The hard part about freelance work for me, a born entrepreneur, is that it vacillates between two extremes: either I’m working on projects that I’m not particularly passionate about or interested in, usually because they’re not going to go anywhere and I know it (and I tell the client), or I’m working on really interesting projects that I know in my heart will succeed or continue to be a success. That sounds awesome, I know, and I’m fortunate to work on more projects like that than those in the first category, but the problem I have is that I’m helping another entrepreneur achieve his or her dream, rather than achieving my own. I love helping people, and I especially love helping people accomplish their goals and dreams, but I hate the feeling of being a hired hand when I should be whipping up my own success. Does that make sense?

As a result, I’ve started aggressively pursuing more entrepreneurial projects of my own, some of which you’ll be hearing about in the coming days and weeks. I’m enjoying freelance work and I’m very grateful to all my clients for the opportunity to work with them, but I’ll be really glad to eventually be done with freelance work. It’s just not as free as I’d like

If you’re a freelancer, let me know how this lines up with your experiences. I would love to hear from anyone considering making the plunge who has questions or comments.

So I’ve got this new idea for a little social web app, and I’m really excited about it because it’s in an area that I’m passionate about, it’s got lots of viral expansion possibilities, and it’s a pretty simple idea, at least in v1.0. Really simple. Like, knock it out in a weekend simple. So I’m going to try and move forward with it over the next few weeks, but I’m having trouble deciding whether I should launch a standalone site or a Facebook application first. My eventual goal would be to have the app as both a Facebook application and a standalone site, as well as iPhone, Android, OpenSocial, and wherever else it fits. But the question remains: which do I launch first?

Arguments in favor of a standalone site first:

• More straightforward development process, whereas developing for Facebook is a pain
• Platform isn’t changing while I’m working, unlike Facebook
• I own my users
• Integration with 3rd-party services feels more natural for some reason?
• May be a better fit than the Facebook audience

Arguments in favor of a Facebook application first:

• Faster development time
• More social integration points, like News Feed, Notifications, etc
• No competition at all on Facebook right now, unlike the web, which has one with a similar idea
• Faster viral growth
• Joyent’s free Facebook application hosting

I’m leaning towards Facebook at this point, but I would love to hear everyone’s thoughts on which approach I should take, and what other questions I should be asking. I’ll be sure and post my decision in the next couple weeks and I’ll be excited to hear what you all think of my little project. Thanks for your feedback below! (hint, hint

I want to be rich. There, I said it. Ever since I was a kid, I always knew that I would be wealthy one day, and I’ve been steadily moving in that direction ever since. I’ve made a lot of mistakes along the way, learned a lot about myself, and spent a lot of time thinking about why I want to be wealthy. In particular, I’ve spent a lot of time thinking about being rich in the context of my faith (I’m a Christian), and in the context of being a good steward of what I’m entrusted with. My good buddy Ben Rasmusen pointed me today to a blog post by John Reel about the lessons learned by getting rich and then losing it all. It got me thinking about this subject, so I’d thought I’d share eight reasons I want to be rich:

Support worthy causes

The way I see it, the more I have, the more I can give away. There are so many organizations and efforts in the world today that need money, and I’m excited to have the opportunity to contribute. I guess when I analyze the rest of the items on this list, many of them are more specific examples of this point.

Give my kids great opportunities

I have been blessed with two wonderful parents who taught me everything I need to know about the things that matter most in life: faith, family, marriage, integrity, etc. However, I don’t come from a wealthy family. My parents are smart people, but neither had the opportunity to go to college, nor did they have the resources to pay my way through college. Thanks to the Navy, I was able to attend a decent school, but I sometimes wonder how things might have turned out differently had I gone to MIT or Stanford out of high school, instead of enlisting in the Navy. I would have had trouble paying for it, and perhaps that’s part of the reason why I didn’t consider those schools to be options. I want my kids to have great opportunities without finances being what’s holding them back. I want to help them pay for school, buy a house, start a business, etc. There’s no guarantee that they’ll have success later, but the least I can do help them take the first step.

Give the underdog a chance

One of my friends just got a job at a company out here in San Francisco and he blogged about their values as a company. One of them is to “help outsiders and underdogs win”, and I can’t stress enough how much I believe in this. I have observed over the last few years that the maxim of “It’s not what you know, it’s who you know” is very true, at least out here. I’m incredibly grateful that someone at CNET saw my resume on Craigslist and emailed me to offer me a job as a product manager. I was just out of college, had pretty much no experience, no connections, nothing. They took a chance on me, and I hope they would say it was a good choice in the end. Money opens doors, and I hope to use any influence I have to hold the door open for other people who may not have the right background or connections. Someone gave me a chance, and it made all the difference.

Own my time

The most valuable resource that any of us have is time. We only get so much of it (and we don’t even know how much), and there’s only so much you can do to maximize the amount that you get. Even if you eat healthy, exercise, be careful, etc., you’re unlikely to live much longer than a century, at least under current life expectancy (this could change, though). The point is, I hate selling my time. I hate that there are things in life that I need and currently, the only way I can get them is by selling my time in exchange for money. Granted, since I’ve started freelancing, I sell my time for a lot more. And I’ve read about people who sell their time for hundreds or thousands of dollars per hour. But in my mind, that’s still slavery. It’s a much more palatable form of slavery, but slavery nonetheless.

My goal is to reach a point where I can live a comfortable life through passive income sources. I will never have to get a job, take a client, or borrow money unless I want to. I can spend my time pursuing the things in life that matter to me. And as a side note, I’m not entirely sure that kind of financial security can’t be considered happiness that money can buy. John agrees with me.

Explore the world

You know that saying about how the things you own end up owning you? Well, it’s true. If you want proof, just try moving frequently, ideally into gradually smaller and smaller places so you have to get rid of stuff. It’s so liberating to get rid of junk that you don’t need or even want anymore. My wife and I sold both our cars when we moved to San Francisco, and I’m so glad. Is it a pain sometimes? Yes. But aside from the financial benefits (which are huge), just the peace of mind of not having to worry about a car is amazing.

I say all that to say that what I’ve come to value more than stuff are experiences. Stuff doesn’t make you happy. My wife and I were blessed to be able to spend eleven weeks trekking around Asia earlier this year, and it was one of the most amazing, enriching experiences of my life. I think travel is one of those things that just fundamentally shifts your perception of the world the more you do it. I want the opportunity to live in some of the world’s greatest cities, explore the world’s cultures, and broaden my horizons by getting out there and seeing how the other six billion people live.

Create wealth for others

I read this fantastic essay about wealth the other day by Paul Graham, a noted angel investor who has funded dozens (or hundreds) of startups, mostly in the technology space. In the essay, he talks about how many people view the world’s wealth as something that’s fixed, and they accordingly view wealthy people as having taken more than their fair share. But entrepreneurs are not working in a zero-sum world. Entrepreneurs actually create wealth, and when they do, lots of other people get wealthy along the way, from the investors, to the employees, to even the customers. Think about how much richer our lives are thanks to the work of Bill Gates, Steve Jobs, and the Google guys. They’ve been rewarded with billions for the work they’ve done, but they’ve given the world a lot of wealth, too, both monetary and in terms of technological advances. I want to create wealth for others and help make their dreams come true.

Change the world

This brings me to the next point: entrepreneurs change the world. The innovations that they create make our lives richer in countless ways. I believe that the next few decades will foster in so much innovation that the last couple centuries will pale in comparison. In particular, I believe that advances in artificial intelligence / robotics, genetics, and nanotechnology will change the face of the world beyond recognition. I want to be a part of these paradigm shifts and wealth will give me the opportunity to fund great startups in these and other spaces, as well as start companies of my own.

Master myself

Finally, one of the best things about getting rich, I’ve heard, is not the destination, but the journey. Becoming a millionaire is something that most people can technically do, but statistically, few of them will. It’s just too hard. Controlling your finances, investing, starting a company, and other paths to wealth are all difficult and require a lot of personal growth and development for most people. One of the best lessons in John’s blog post is the first one: “I can get rich.” Once you’ve done it, it’s much easier to do it again, because you believe in yourself, and because you’ve mastered yourself, at least to some degree.

Conclusion

I’m not waiting until I’m “rich” to do any of these things. I believe that building wealth is a process. There aren’t shortcuts, per se, though there are methods to get there faster and smarter, but they usually require more risk, more dedication, and more time. Regardless of how I get there, I hope that if and when I do, I’m able to keep these things in perspective and be a good steward of what I’ve been blessed with. I’d love to hear your comments on the subject.

Geez…I have to get on here more often. The last few months have been crazy, and as usual, I’m juggling a lot of projects and ambitions. My latest projects are two eight-week-old beagle puppies that my wife and I recently acquired. They’re a handful, and the last two weeks have blurred by, but I think we’re finally starting to get into a routine with them, which is a relief. Hopefully I’ll be able to start getting up at 415am again and knocking stuff out.

One of the things that I’ve been meaning to do for the last six months or so is come up with a unified goal plan for my life. I’m a pretty ambitious person, sometimes too ambitious, and I’m an optimistic perfectionist with procrastination tendencies, which is to say that I have good ideas, turn them into HUGE ideas, decide they have to be perfect, put them off, and then get depressed because I’m not meeting my goals. That’s a bit of an exaggeration, but you get the idea. Anyway, over the last few years, I’ve learned a lot about myself and my own shortcomings and I’ve come up with a few systems that work well for me, when I’m disciplined enough to use them.

1. Goals - Having a solid path is crucial for me
2. GTD - Managing my time
3. Involving other people in my goals

Over the last year, I’ve adjusted to freelance work, but there’s a lot of things that have slipped a little over the past twelve months. It finally really hit me a couple weeks ago that it’s time to stop messing around. It’s time for me to get those things under control, and Project Goalpost is my code-named attempt to do that.

Project Goalpost is an effort to unify my goals from all different areas of my life, streamline them, align them with my current projects, devise a plan for goal review and habit building on a regular basis, request accountability, and incorporate a GTD workflow that includes these higher priorities.

Every six months or so, I put together a new list of goals, based on what’s going on in my life. This means that I have lots of lists of goals and priorities, spread throughout my life…in notebooks, on Google Docs, on my hard drive, in my email, etc. These goals are often in conflict, are rarely reviewed, and many are not SMART.

On top of that, my use of GTD has really fallen by the wayside over the last 6-8 months. The difference in utility from using GTD at 80% and using it at 100% is incredible…in order to be truly effective, you must use it constantly and consistently. I have not been, and thus most of the utility is wasted.

What I’ve decided to do is take the following actions:

1. Collect all my goals and lists of things I want to accomplish from all the various places they’re stashed
2. Consolidate, eliminate, and add any new goals to the list
3. Break the list into major categories (Personal, Physical, Real Estate, Career, etc) and time frames (short-, medium-, and long-term)
4. Ensure every goal is SMART
5. Ensure all categories have roughly the same amount of goals, to help ensure well-roundedness
6. Compile into a master document
7. Destroy or archive all source materials to avoid distraction
8. Add all initial steps towards goals to GTD system
9. Devise a schedule for goal review (daily for short-term, monthly for medium-term, every six months for long-term, etc)
10. Determine what projects have relevance to goals, and ditch the ones that don’t
11. Ask five or more people to review my list and help hold me accountable
12. Post my list here and ask my readers to keep me accountable

These are typically the kinds of things that I would do on my own, without telling anyone, but I need some accountability. I need someone to ask me how my goals are going, so I’m laying it all out there. With the possible exception of a few very personal goals, I’ll be posting the results of Project Goalpost hopefully within the next few days.