As noted in my previous blog post on this topic, the first quality I believe is necessary in a great speaker is for them to be educational in some way. In my recent bout of conferences, I have seen speakers who fall all over the quality spectrum, but the ones that were truly good ensured they shared something new with an audience.

In the interest of a clean comparison, I will use the same list of speakers — covering the spectrum of topics — across all three categories. A few of these speakers I saw more than once, in which case my ranking takes into account each time I saw them in a public speaking setting, even if the format changed (i.e. if they were a solo speaker in one case vs. on a panel with others in another).

	Charlene Li Educational Value of Content: B Details:Charlene’s background as Forrester analyst gives her access to a lot of information. This is certainly helpful when pulling together a presentation. While there wasn’t anything tremendously earth-shattering in her information either time I saw her speak, her content was solid and her examples were clear and well-presented. Particularly in her main address at SXSW, however, she made at least one leap of logic that she was clearly hoping the audience would share, and seemed a bit surprised and unsure how to respond when there was a difference of opinion. Her assertion was that Google “wouldn’t dare” violate their user’s trust by compromising their personal data. She left this as a blanket statement without explaining on why she felt this was the case. An audience of 1,300 people were not as universally quick to buy into her belief as she was.
	Chris Anderson Educational Value of Content: A Details:Though probably best known as the Editor of Wired and the author of The Long Tail, Chris was on-stage at SXSW (with Guy Kawasaki) principally to discuss his new book, Free. From a content standpoint, Chris knows his stuff. And I was in a constant scramble to jot down notes of things he was saying that I wanted to research in more depth later, because he was making some great points and doing some very interesting historical and economic comparisons. He clearly had the material for a graduate seminar that would have been very interesting, and it was too bad the schedule and format did not allow him to share more.
	Chris Brogan Educational Value of Content: D Details:In the multiple times I saw Chris speak in the month of March, I am not sure I honestly remember once where he shared a piece of new information. He gets props in other areas, but educational value was very low. He had a couple of anecdotes that were insightful, and the questions he had for Guy Kawasaki during their “fireside chat” at PubCon elicited some good discussion, so he gets a bit of credit on that front. By and large, though, the strengths Chris demonstrated during the times that I saw him were not in the educational value of his content.
	Gary Vaynerchuk Educational Value of Content: B Details:Gary is a sneaky devil who walks the line on content. In a perfect situation, he will spend his entire talk on audience Q&A and entirely avoid the need to generate original content himself. He’ll ‘crowdsource’ his content by leaving it up to the audience and simply answering their questions. So I’d mark him down points on that, but then give him high marks for providing good, detailed, tactical answers that are chock full of actual educational content. And, as a person with a tremendous curiosity and range of interests (and deep expertise in some areas), he ends up being a font of juicy nuggets of information — assuming someone thinks to ask questions in the right areas.
	Guy Kawasaki Educational Value of Content: C Details:Aside from good anecdotes, Guy seems to reserve most educational content for his written efforts (Twitter, blog, books, etc.), and uses his speaking engagements for the “lighter-weight” aspects of personal branding. To be sure, some of his anecdotes are phenomenal, but they usually play more towards humor and simply being “good stories” than being truly valuable, reusable lessons or insights. Though, to be fair, he did toss out a few gems here and there, and out of the handful of times I saw him speak, I did get a few particularly good ideas — though these seemed to be very tool-specific, based on the opinion of a self-avowed technology lover. He did also do a good job of eliciting good content out of Chris Anderson during their shared event at SXSW.
	Larry Lessig Educational Value of Content: A Details:Larry is a lawyer, a professor, a writer, an activist and the founder of Creative Commons. He is all about the content (literally and figuratively, as a matter of fact). I’ll cover style in a subsequent post, but his content was detailed, specific and entirely relevant to the topic at hand. If you could write fast enough to keep up with him, you’d easily get valuable information when he speaks.
	Matt Cutts Educational Value of Content: A Details:Matt knows his stuff cold. Inside and out. And he is there to share information. So Matt gets all A’s when it comes to content. As a developer, Matt can give super technical information (and did); but as a smart speaker, he knows how to de-geekify his content when his audience is not developer-centric. So he gets double-points on content: not only is it valuable, but he also de-mystifies what could easily be intimidating material and makes it extremely accessible for non-technical audiences. He also has a great advantage over some speakers when it comes to content: because his main topic (search) is a constantly evolving field, his material is always being updated, so there is no real danger of content stagnation with Matt.
	Tony Hsieh Educational Value of Content: A Details:From what I heard from people who’d seen Tony at previous speaking events, his content didn’t really change much, so if you’ve seen him once, you may have already heard most of what he had to say, but if you haven’t seen him yet, make sure you do at the first available opportunity. His message on leadership, management, building a company, brand and culture is packed with valuable information. Like Guy Kawasaki, he uses lots of anecdotes. The difference is that his are targeting a point, rather than merely being entertaining. His stories are well-selected to illustrate his points, and his points are insightful and compelling. I found it common that he would speak on topics I knew a lot about, and still managed to say something new.

So these are my scores for the educational value of the content. As I’ve mentioned before, I saw tons of people speak over the course of conference season to date. I selected these examples here because they are well-known names most people have heard of. I also selected them because they represented a great cross-section of public speaking strengths and weaknesses in the three areas I outlined as essential: educational value, authenticity and emotionally connecting with the audience.

Have you seen any of these speakers and have different experiences about their content?

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I’ve been very fortunate recently: in my role as Managing Editor of Social Computing Journal (formerly Social Computing Magazine), I’ve been able to attend a number of conferences that I would not have previously been able to find the time or money to attend.

In quick succession, I have attended PubCon South, SXSWi and Web 2.0 Expo. And each of those conferences have provided me with great opportunities to attend talks given by people whose work I follow (to one extent or another):

• At PubCon I heard Guy Kawasaki, Chris Brogan, Lee Odden, Wayne Sutton, Matt Cutts and more.

• At SXSWi I got to see just about all of those, plus Penelope Trunk, Robert Scoble, Louis Gray, Charlene Li, Tony Hsieh, Chris Anderson and Gary Vaynerchuk.
• At Web 2.0 Expo, I got to see some of those same ones again, plus Peter Kim, Jeremiah Owyang, Stowe Boyd, Dion Hinchcliffe and more.

There were some stark and compelling take-aways for me as I reflect back on the past month and all of the conference activity:

The Social Media and Enterprise 2.0 space is an echo chamber.

There are a handful of smart people who keep saying the same thing over and over again to the same people. And, unless you just enjoy attending talks for the sake of attending talks, once you’ve seen them once, you can probably skip them at the next conference. I had really hoped that the people I saw at more than one conference would have something new to say; and not once was that the case, which was disappointing. While I understand that they do not assume there will be many people who follow conferences around all over the country (other than media), in an overly-blogged world, recycled presentations will fast become audience killers. This is something that professional speakers — especially in the tech/media space — are going to have to start recognizing and managing appropriately.

The people I was most looking forward to seeing are never the ones I ultimately find the most interesting.

Case in point: I did not even realize that Louis Gray was on a panel at SXSW, and yet his material has probably been the single most valuable of everything I got (on a personal, practical, daily level). Chris Anderson, Matt Cutts and Tony Hsieh also fall into the ‘not quite on my radar’ category. Each one of them I saw by virtue of fortunate circumstance, and each one of them proved to be a great highlight I never expected. The converse is also true: in almost all cases, the people I was most looking forward to seeing were the ones who ended up being the most disappointing — and always for reasons of style more than content.

Some people are just better in writing and should give up the delusion that they make good speakers.

As someone who has been online since 1996, I learned a long time ago that the ways in which someone presents themselves online is rarely a true reflection of their real life personality. And, in almost all cases, real life is the disappointment. This may be even more true now that more and more people are getting online and using “personal branding” as an opportunity to establish a bit of an online alter ego that is just smarter, funnier, more clever and more interesting than they are in real life. But before you get up in front of an audience, do a personal inventory to see if that’s the case. Because I saw far too many people speaking in public who were either disappointingly annoying or abrasive or, worse yet, simply boring.

The “Social Media Celebrity” phenomenon is gaining momentum and proving to be a bit nauseating.

I freely admit, I am not a celebrity hawk. In fact, when it comes to pop culture, I deliberately practice Tim Ferriss’ “low information diet” technique. It took me months after the rest of the world started talking about it for me to have any idea who the Octomom was, and even then, it was only because my husband was recapping her insanity one night while we were walking the dog — and I was trapped, with no way to escape. In my youth I used to enjoy a bit of it, but after a few years as a fan geek, I got it out of my system.

And now, watching the celebrity that has erupted around different individuals in the social media space — especially the big ones like Guy Kawasaki, Chris Brogan, Robert Scoble, Charlene Li, etc. — is something I find a bit unnerving. Watching the fan reactions to many of these industry leaders at the conferences was a bit like watching the cast of Star Trek walk on-stage at a Sci Fi Convention. It was never clearer to me the extent to which this new space is a complete convergence of business and entertainment. Because, while I may be there because this is my business and these are business leaders whose insights I am looking to learn from, other people are there as fans. And we’re all mixed in as part of the same crowd, which is a very unusual — and not altogether pleasant — dynamic.

All in all, it has been an interesting conference season. Interactive Austin is coming up in a few weeks, which is another small local one that I am particularly looking forward to (and speaking at). Whether or not I attend Enterprise 2.0 in Boston in June remains to be seen, though I would be very interested to see first-hand how some of this plays out in an enterprise-specific environment.

So, which was the best of the conferences from the past month? Since Pubcon was so small, it’s probably not a fair comparison. (And, in all honesty, the size of PubCon made it an incredibly intimate experience, which was great; and because it was affordable and local to Austin, it was absolutely the best local networking event I have attended since arriving in town last fall.)

Which just leaves the two big ones: SXSWi vs. Web 2.0 Expo.

No comparison. SXSWi was the better experience. Higher energy level. Higher attendance level (at least it felt that way). Higher activity level. A broader spectrum of topics, speakers, activities, etc. And I can say that, even though I didn’t attend a single party. (Socially, I took more advantage of Web 2.0 Expo, since it was my first visit home to SF in a year, and saw a ton of friends.)

What about you? Any interesting insights from conference season so far?

My Conference Season 2009 Posts:

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This book review was written for Joyful Jubilant Learning‘s March book reviews. I am posting it here for my own personal timeline.

Barbara Stanny‘s “Prince Charming Isn’t Coming: How Women Get Smart About Money” is a great story with a problematic title. Unfortunately, it is also billed as a How To book, which is where it falls a bit short.

Title Turn Off

While the title of the book is provocative, it is a bit of a turn off for the two types of women who most need it:

• Those who – like Ms. Stanny herself – are waiting for Mr. Right to come along, take care of her (and her money) and leave her to idle away her time at luncheons and charity events without a care in the world.

• Those who – like me – are self-sufficient, never expected anyone to take care of me, and yet have some very destructive and unhealthy financial habits that haunt us, no matter how high an income we ever have.

For those who are expecting Prince Charming, the title is frightening. For those who scoff at the idea of Prince Charming, the title is insipid.

The Story

What Ms. Stanny does do well, however, is outline a great story: her own. As the daughter of one of the founders of H&R Block, not only was she a woman who should have never had to worry about money, but she was also someone who should have had enough exposure to good money management practices that she could have avoided finding herself in a financial mess.

Of course, the problem is that Ms. Stanny was raised by parents who brought her up to find a good husband who would take care of her, and to whom they could pass over the keys to her trust fund, and pat her on the head and send her on her way. That all worked just fine until it turned out that her Prince Charming was more of a frog with a knack for expensive – and unsuccessful – market speculation that eventually wiped out her cushy trust fund.

The How To

Ms. Stanny falls a bit short on her objective to make the book a great How To lesson for women. She does a marvelous job conveying precisely why women need to take care of their own financial destiny, but she does a less concret job explaining how. Authors like David Bach and Suze Orman offer much more tactical and actionable advice.

However, where Ms. Stanny hits a home run is making the case that learning these things are something that every woman should do as soon as possible. As a result, I have given a copy of her book to just about every woman I know – from friends with six-figure incomes and compulsive shopping problems, to my 16-year-old neice.

The only problem is that everytime I give it to someone, I feel compelled to talk fast to get them past the title.

The good news, however, is that in recent years, Ms. Stanny has written more books that are also worth reading (including Secrets of Six Figure Women), and has built our her online presence to include a blog where she does often offer the tactical advice her book was lacking.

The End Result

Like many authors, Ms. Stanny’s first real effort showed promise and some value, but didn’t quite hit the mark dead-on. “Prince Charming Isn’t Coming” would be one of those. However, it is still a quick, worthwhile read and something that most women will be able to relate to at least a bit – no matter what their relationship with money. It also does a great job of laying the foundation for much of her later body of work, which holds increased value.

What is More Useful?

How many of us know exactly what we need to be doing to get our finances in order, but just don’t do it – out of laziness, habit or denial? How many of us feel overwhelmed with anxiety at the prospect of dealing with our finances and chose to play ostrich instead? How many of us just really don’t have the first idea where to start and are truly baffled at how to begin to dig ourselves out of our financial hole?

Where I give Barbara Stanny the most credit is in tackling – and sharing her own experience with readers – the embarrassment of being a woman who “should have known better” but chose denial and avoidance for as long as possible before taking control of her finances herself. She could have taken a different approach to getting her message across, but she did a compelling job of sharing her own journey, including the embarrassing parts, to help her readers get past the intimidation of a subject that doesn’t need to be as crippling as it often is.

So, if you are looking for a step-by-step plan to turn your finances around, this book wouldn’t be your greatest resource. But, if you are one of millions of women who knows that she needs to tackle her issues with money, but lacks the motivation to truly dive into such an overwhelming and unappealing pool, this book could be a great place to start. By the time you’re done, you’ll feel like you just left a session with a great cheerleader urging you on to the next goal. And sometimes that is what we need before we can start planning next steps.

So what is it that you need? Detailed actions to take? Or merely the motivation to do what you already know you need to do?

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I recently put my “Sex and the City” DVDs on while doing some work around the house, and was reminded of the two things about the show that — no matter how much else about it I loved (and there were plenty of things in that category) — that bother the daylights out of me every time I watch the show.

1. Almost Everything that Comes Out of Charlotte’s Mouth
Charlotte is a hard one for me throughout the course of the series, because while I appreciate the take that Kristin Davis expresses about her (that she ‘aims high’ and goes after what she wants), I find so much that she says and does really offensive and clinging to painfully frustrating sexist cliches — many of which I thought were completely dead until I moved to New York.

There are a few quotes in particular that stand out, and which — every time I hear — make me want to shake her until her teeth rattle. “It’s normal for the man to make more money!” (which is not actually true). And, “If you own and he rents, then the power structure is all off. It’s emasculating. That’s why I rent!” And, “Everybody needs a man!” Grrr.

2. Carrie’s Fiscal Irresponsibility
This, to me, is the bigger offense in the history of what was generally a very good show. While Charlotte pisses me off on a regular basis, my recent time in New York made it very clear to me that sexist cliches about women that I had always thought were long dead were, in fact (much to my horror), still very much alive. And while I may find them offensive and retrogressive, I can appreciate that as a character, Charlotte represents an archetype that (sadly) is still in existence.

Carrie’s bad financial habits, however, are another matter. What I find most aggravating of all is that there were points during the course of the six years the show was on the air that the topic did come up, and where it was at least acknowledged. Unfortunately the writers took the cowardly way out, and never actually dealt with the underlying issue directly. And because it is one that is a major, major issue for “successful” women, it’s something I find very sloppy in a show that spent so much time focusing on the things that impact women’s lives.

At the end of Carrie’s relationship with Aidan, she was faced with the prospect of being evicted from her apartment unless she could come up with the money to buy it. This was the only point during the series where her (bad) habit of racking up extensive credit card debt buying over-priced footwear was even acknowledged as something that went beyond irresponsible, but was out-right hazardous to her financial and personal stability. And in an uncharacteristic display of convenient fairytale writing, a year later she got a book deal that suddenly made her financially secure; and then she ultimately ended up with two different wealthy men, who took care of her, and made her financial bad habits non-issues.

I detest this cliche. And while I appreciate that there is a desire for fantasy that is a huge part of any show, this one bothers me simply because it is so destructive to women. While there are plenty of arguments to be made for the damage that women inflict on their own earning potential by opting-out of a career track to live on a Mommy-track instead, that is something that — while I don’t understand — at least is an actual choice. And while plenty of women may regret it later, the fact is that they make a choice to do what is best for their family in the moment, and in the end, they have to live with the results.

What is so insidious about the financial management question, though, is that so many women are still taught (either implicitly or explicitly) that they don’t need to worry about managing their own money. And that just makes me crazy. What is worse, is that in a country where less than 10% of all women make more than $100,000/year, so many of them still live paycheck to paycheck.

Now, to be fair, there are some environments that encourage that behavior more than others. And, in Carrie’s defense, New York City is probably the biggest offender. There is no city in this country that is more readily positioned to quietly absorb your money without you ever realizing what is happening than NYC. Want a cab home after a long day? No problem. Ten bucks. Want to grab some Chinese food instead of trying to cook in a ridiculously small and impractical kitchen? No problem. Ten bucks. Want a cute purse this street vendor is selling? No problem. Fifteen bucks. Want to go out with some friends after work? No problem. Ten to fifteen bucks per drink. And a Manhattan studio apartment (depending on the neighborhood) can commonly be counted on setting you back around $2500 per month — and that’s for rent! Before you know it, a $100k salary is gone and that’s even before you factor in ridiculous shoe-buying habits.

Now, let me be clear: I also have a weakness for shoes. I have over forty pairs, and take endless grief from my husband about them. I also have a rather ridiculous number of both hats and purses, which, frankly, are even bigger weaknesses for me than shoes. However, make no mistake: if you are spending $1000+ on a pair of shoes when you can’t pay off your debt and you have no savings/retirement, that IS irresponsible. Period.

In her very good book (with a positively insipid title), “Prince Charming Isn’t Coming,” author Barbara Stanny discusses the real danger to women who don’t take control of their finances: they end up at the mercy of the forces in their life that DO control the money — quite frequently a father or husband. But what happens when that person is no longer there? Or, worse yet, what happens if the person you were counting on to ‘protect you’ turns out to be the one from whom you need protection? I gave this book to my niece when she was 15 and told her to think very carefully about what she wanted her life to be like.

I’m a big fan of David Bach. The first book of his I read was, “Start Late, Finish Rich” (ironically, a Christmas gift from my father). But the book for which he is actually more well-known is “Smart Women Finish Rich.” One of the most valuable points he makes (and the one for which he’s become the most famous) is, what he calls, “the latte factor.” By that, he means those little nickle-and-dime things we spend money on that add up to significant amounts of lost money over time. They are the habits we don’t think about, but they are some of the things that hurt us the most. And whether your weakness is shoes, $4.00 lattes, bottled water, cigarettes, or (like me) never quite getting around to submitting expense reports (and ultimately having to eat expenses that would be reimbursable if you just got them in on time), it doesn’t matter. His point is that we all have some habit somewhere that is costing us more than we usually stop to acknowledge.

Penelope Trunk argues that it’s always wise to be a rock star at work, because it ensures more options and control over your life. I would go a step further and say that no matter how successful you may ever be at work, if you are letting your finances control you instead of the other way around, then you are a hamster on a wheel who is undermining her own success. And while this is certainly an issue for men as well as women (especially in NYC, where it is a pervasive problem), since professional women typically face a consistent and predictable list of obstacles when it comes to attaining success in the first place, it’s a simple case of shooting ourselves in the over-dressed foot.

I had a brief moment where I had been truly hopeful that the “Sex and the City” writers would actually show a theme of Carrie trying to cut back as she juggled two jobs and then worked to repay the loan she ended up taking from one of her best friends in order to buy her apartment. Sadly, the show disappointed me and did not revisit any of those points after showcasing the question in a single episode. And since Carrie’s spending habits never changed, I was ultimately disappointed that such a great opportunity to make a valuable point was neglected by a writing and production team that typically demonstrated such willingness to tackle all kinds of other difficult issues.

I love the Jimmy Choo store on Madison Avenue as much as the next shoe junkie. But there is something I love even more: having options. I don’t have to put up with a boss that I hate. I don’t have to pass up a great 24-hour sale on a vacation package that comes my way. I don’t have to lament needing to pass on a tremendous business opportunity that is presented to me. I can pack up, leave New York, and move half way across the country to Austin, TX without having a job lined up if I decide that’s what I want to do. The choice is mine. And no matter how good a pair of $1200 shoes could ever feel, they can’t ever compare to that freedom.

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In my recent quest to collect as much information as possible to educate myself about finances and investing (and area in which I am negligently ignorant) I came across a book that has proven to be highly valuable, if not a bit unsettling. It’s “Prince Charming Isn’t Coming: How Women Get Smart About Money” by Barbara Stanny.

Now, having spent my life as a highly contrarian, radical feminist with HUGE aversions to the idea of marriage, I have never in my entire life succumbed to the ‘prince charming’ fantasies that are apparently still rampant among women. In fact, I am often surprised when I meet women who have them, because the idea seems so out-dated to me that I find myself feeling like I am looking at an old hand-crank record player: it’s one of those things I know existed at one point, but I never really thought I’d see one in real life. So imagine my surprise when, while reading Stanny’s book, I discover that — though my motivations may not always be the same — I have spent my entire adult, professional life demonstrating the same type of behavior as the women she writes about (including herself) who spend their lives being financially short-sighted because of an underlying belief in the myth that one day ‘Prince Charming’ is going to show up and financially rescue her.

Truly, the realization is shocking. And more than just a little appalling.

I recall very vividly a year and a half ago, when my partner and I were meeting with our financial planner for the first time. The meetings would leave me feeling so blatantly hostile and antagonistic than I’d want to scream at someone just for the hell of it. I wanted him to lead dealing with all of this stuff, and I didn’t want to have to do anything more than sign my name on the dotted line.

From not long after we started living together, we’ve had a joint bank account and combined finances… which he has mostly managed. The second I handed everything over to him, I mentally checked out. Intellectually I know better than that. And if someone had told me I would do that, I would have been offended and argued that I would never be that stupid, “girly” or irresponsible. I am the primary breadwinner. The idea that I would voluntarily turn into a mental marshmallow and hand the reigns for EVERYTHING over to someone else is utterly preposterous!

And yet, shockingly enough, that’s precisely what I did.

I recently started reading David Bach’s book, “Smart Couples Finish Rich.” I like David Bach’s books a lot, but this one I have not yet been able to finish, and now I realize why: Bach strongly argued that a couple must deal with their finances together, and the idea of having to do that again was so monumentally unappealing that I stopped reading the book.

Now, my reasons were not always the same. I never specifically wanted a man (husband, boyfriend, partner, whatever) to manage my money, I just wanted anyone who could/would do it. I always just figured it’d be a bookkeeper or financial planner.

Much like I never intended to do my own housework, I just expected that I’d have a housekeeper. In point of fact, one of my underlying reasons for being so career-driven has always been so that I can hire the help that I need to manage the daily tasks that I thoroughly dread. I’m really not kidding. Most little girls grow up wanting to find a rich husband who will take care of them. I grew up wanting to be a highly well-paid professional who could just hire whatever personal staff I needed to deal with life’s unpleasantries.

It’s actually only been in the past year that I’ve started learning how to deal with domestic chores. Because I hate them so much I have spent my life avoiding them, and I’ve finally come to realize that dealing with my money is precisely the same as dealing with the dishes (which is the household chore I hate more than all the others combined). And, amusingly enough, now that I’ve learned to manage how I approach it, I’ve started discovering that they are infinitely less miserable than they have ever been before. Ditto, once again, my feelings about dealing with money.

One of the other things that I’ve recently realized is that I’ve always used being a workaholic as an excuse to not deal with my money. Educating myself and getting up to speed enough to deal with it intelligently would detract from work, and — just like a love life — anything that detracted from work was not welcome in my life for years. I tend to view my time as valuable, based on the rate that my employer pays me. So, at about $50 per hour, I didn’t want to squander that time on something that wasn’t directly valuable.

Admittedly I can be a bit slower than I like to admit sometimes, because the absolute STUPIDITY of that logic only just fell into place. My time is worth far MORE than $50 per hour. And yet the only way I am going to have a net worth greater than that is if I make sure to create it myself. If my employer if paying me enough to come out to $50 per hour, then that’s our arrangement and that’s fine. I will give them the time they are buying. But they don’t get “freebees” thrown in on top of that! Not when taking that time I have been donating to someone else’s bottom line can be re-shifted to my own education and financial future to INCREASE the over-all value of my time.

My other big obstacle is political. I am a socialist. As such, I’ve always been highly conflicted about having (as my Mom used to say) a “champagne appetite on a beer budget.” It’s actually taken until a couple of different events converged recently that I’ve been able to reconcile my internal conflict on this topic.

I recently told someone that, just because I am a socialist who doesn’t buy into the notion of money-worshipping, didn’t mean that I don’t know how to play the capitalist game. And that, as long as that is the world in which we are living, then those are the rules I need to excel at unless I’m going to drop out of the race entirely and be content to live on a commune somewhere.

The truth is, that would be an option. My younger cousin actually lives on a commune. But that is absolutely up her alley. For all of my political ideals, I do have expensive tastes, and I like certain creature comforts that simply require money. So a long time ago I decided (mostly unconsciously) that I was going to attain a level of success and financial independence that would be required to have the lifestyle I wanted. I have done that. But what I haven’t done is the conscious work that goes along with it to properly manage and grow my money in such a way that I would not always be in jeopardy of being beholden to an employer.

So, now it’s time to do that.

If there is one thing that I know it is that my political inclinations drive me to wanting to do certain types of work that do not pay what I am accustomed to making. As a result, I have always had to make a choice: do the type of work that truly excites and invigorates me and make shit for money, or find ways to be motivated to do work that pays well. Now, as I learned from one of my former employers, I can only push that envelope so far in the “whore” direction before no amount of money is worth supporting an organization I just find offensive. So I look for places that are politically in line with my beliefs for the most part, so there is nothing out-right egregious about my working for them. Yet on a daily basis, this is not the truly fulfilling work I would most like to be doing. So I am making a compromise. It’s a perfectly tolerable one (for the time being), but it’s still a compromise.

I know myself well enough to know that eventually the compromise will no longer be worthwhile and it will be time to go. So I can move to another job, but it will be the same thing all over again. And eventually that will be too much, too. In the end, the only thing that is going to make me happy is to be able to do political and socially-valuable work… the kind that pays shit. So in order to prepare for the day when compromising is no longer acceptable to me, I need to take advantage of being paid well in the meantime to build up my own financial status to the point that when that time comes, I can take a job without having to worry one way or the other about how much it pays.

And, the fact is that I am a socialist, but I am also a pragmatist, and I fully acknowledge — perhaps resentfully — that money is the key to having the power to make your own choices and not being trapped. And if there is one fear I have in the entire universe, it’s being trapped. I’ve always only ever considered that fear on an emotional level and in the context of relationships, but it’s equally true of finances. And now that I see it in the same way, it is crystal clear to me that I’ve spent the past decade putting myself on a course that is going to take me to my worst nightmare: being (financially) trapped.

For the first time in my life, I am actually excited about the prospect of tackling this. It is no longer innately intimidating or aggravating or antagonizing or too tedious to have the patience for managing. It’s part of what I need to do for me. And it feels bizarrely good.

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