The biggest thing about turning 35 for me is that I’m now either teetering on the brink or officially disqualified from  several emerging leader support systems that have been critical to me in recent years. Which is as it should be … time to send the elevator back down.

With the combination of birthday + writing exercise fresh in my mind, I wrote a letter to myself at age 25 when I was just starting out my career. And if I had read this when I was 25 I would have been all like “I am totally doing all this already.” Because I knew everything. Anyway …

Dear 25-year-old self,

It’s 2001, which means you are living in New London—boyhood home of Eugene O’Neill, current home of poets, puppeteers, playwrights and should-be rock stars. The Wailing City. It’s small and gritty and it’s on the water and you love it. You just started work at The O’Neill and you love it. You are directing plays with amazing creative collaborators and you love it. Not having any money is hard … but it won’t kill you. Not having heat will drive you crazy so move already! You will be so much happier.

You already know this, but these are the big years. You are nostalgic for these years and you are living them. There will never be more bonfires on the beach, late-night puppet shows, poems, exploring abandoned buildings, riding the subway, coffee in Brooklyn. Over time you will become less dazzled by someone’s job title or the fact that they live in The City. People will become less interested in dazzling you and more interested in opportunities for collaboration, less interested in romance and more restrained in their joy, less interested in dreaming and more interested in networking … so be dazzled by everyone and everything. Try to stay up late (although you are bad at it). Be alert, be inquisitive. If there’s an experience in front of you, have it. See as much theater and live music as you can.

I wish I could tell you, 25-year-old-self, to say yes AND no more often. To have difficult conversations before it is too late. To drink tea before asking for that raise because if you don’t you will start crying and it won’t matter that you prepared a letter detailing your expanded skill set and responsibilities. Make decisions. Commit. Stop trying to keep every door open, you can’t keep every door open, nobody can keep every door open. As your Russian acting teacher says, “be bravier.”

Savor lazy mornings and slow weekends. Be patient, the future will find you sooner than you realize. Don’t be bullied, and don’t be so hard on people. You don’t have to be nice to someone just because you feel sorry for them, that’s your Midwestern roots talking. You do have to be compassionate. Age and experience really do make a difference in this area.

And … although these are the big years, years of glamour and discovery and adventure, there will be other years. Years of deeper feeling, shared years, meaningful years, years of change. Be dazzled by them all, appreciate them, live in the moment. Keep learning and changing. As they say at The O’Neill, “risk, fail, risk again.”

Your friend,

Future Lex

*p.s. despite rules and guidelines, I think when we stop emerging, we stop living. Corny and true!

When I worked at the O’Neill Theater Center, one of our mottos was “Risk, Fail, Risk Again”. This especially applied to our student actors, but lately I have been thinking about risk in terms of career trajectories. As an emerging leader in my 20s, so much of my life seemed caught up in the first career choices I made, that it had all the drama of this (awesome) Judy Garland classic.

Feeling trapped in a dead-end job, or not getting the job of your dreams can seem downright tragic when you work for a nonprofit. We’re not just looking for a job. We are looking for our opportunity to Transform Lives Through The Arts. Or Education. Or whatever.

But inevitably, if you are taking risks and  reaching high enough and looking for all of the experiences that emerging leaders should look for, unpredictable and wonderful and disappointing things will happen. Some of my Bay Area peers—Evelyn Orantes, Maia Rosal, Marc Vogl and Ellen Oh—will be sharing their personal experiences at “Career Trajectories—Not All Straight Arrows,” as part of Americans for the Arts’s 2009 Creative Conversations series, presented by the San Francisco Bay Area Emerging Arts Professionals. It is next Tuesday, October 13 at 7pm at the Oakland Asian Cultural Center. It is $6. And, you can register in advance here.

Hope to see you there!

I’ve been thinking a lot about Yosi Sergant, and reading the debate on Jeff Chang’s blog. I’ve been thinking a lot about politics, and provincialism, and wondering if it is possible to write an interesting blog anymore if you are The Administration.

Why do we become The Administration? I say this, half-joking and half-horrified, because a grassroots leader I know is referred to that way by her staff. “The Administration” refers to just one person.

I know a lot of emerging leaders who want to be the director of an organization someday. I don’t know any who want to become “The Administration.”

Sigh … in a perfect world the Yosi Sergants would wield ongoing power and have infinite connections to serve their mission without joining the NEA. But that is a tough row to hoe. In a perfect world we’d all be making art in the service of an insurrection, by the people for the people. But in this world, we can’t even use the word insurrection without having to defend it. And the most talented insurrectionists I know are also talented at finding money and administrations to back them up.

Back to the blog–I guess I’m feeling a little doubt these days about what’s safe and what’s fair. I’m not giving up the blog. But it merits more thought.

And on “emerging leadership” … I’ll be giving a very short talk on behalf of the San Francisco Bay Area Emerging Arts Professionals as part of Friday Nights at the de Young, this Friday night. If you are wrestling with these same issues, come join us–it will be good times!

But a funny thing happened on the way to submitting that grant application. I started getting excited about marketing again. Specifically, the potential for breaking open a tired old myth (Full-Time Marketing Director + Hotshot Publicist=Stellar Attendance) and doing things more efficiently and effectively. I used to scour the newspaper and online listings for interesting things to see and do, but here in San Francisco, that means sifting through 435 listings on a lazy Sunday, and those are by no means comprehensive. The grassroots innovators rarely show up in the newspaper anymore, and the most compelling invitations come from artists, curators and collectives.

I get dozens of Facebook invitations each week and I’m still not sure I know a single person under forty who can entice even fifty people to an arts event where there’s not free booze. How large is the disconnect between new technology and true relationship building when it comes to arts participation? I hope the gap is narrowing, but I fear there is a schism that puts small and mid-size arts organizations at a disadvantage.

As a friend reminded me this weekend, going to the theater (or any arts event) is an adventure that requires effort and risk … and in an era of empty pockets and full schedules, the best publicist in the world can’t compete with word of mouth when it comes to filling a room. Logic would say that facts and accuracy count for more than opinion, but science is proving that wrong.

So … whether or not I attend Boot Camp, I am left with a few questions:

• Can relationship building with technology be taught? Who should do the teaching?
• How can Institutions (defined as: more formal organizations, often with more formal relationships and more liveable compensation to artists) blur the lines between marketing and art-making without sucking up all of the time + energy of artists, aka making them “jump through more hoops” just to have a show?
• What are the intergenerational  aspects of new technologies in marketing (positives and negatives)?

And, on a very micro-level … what does this all mean for my organization’s database, website, budget, et cetera?

Any answers out there? Advice, links, book/study recommendations welcomed.

As an added bonus, Rebecca is a trained life and leadership coach. This means that I also got to pester her with my friends’ (ahem) career conundrums, all in the name of journalism.

Seriously though, Rebecca gives some good advice, comments on Richard Florida, shares her must-read list, AND points out the bright lights of the leadership track at Convention.

Interview excerpted from The Art Agenda. Broadcast on 88.1fm, WESU, Middletown on June 12 2008.

As a relatively recent Massachusetts transplant, I have been impressed by the ability of state arts leaders to express the value of the arts, generate discourse, and successfully lobby for arts funding. Not everyone agrees that this new post is a good one, and future debates are alluded to in today’s Boston Globe, alongside accusations of “pandering to fads.” This job would be a challenge for anyone, but also an opportunity for exciting change and growth. I look forward to seeing what Massachusetts (and Jason) think of next.

(Thank you to Rebecca Borden at Americans for the Arts for the tip!)