What happens after you design the life of your own making? What then?

the new work

Boomers will be our ruin, was our constant refrain in the late 90s. This was a time when we actively practiced our apathy, regarded the internet with a mixture of interest and suspicion, and carried cellular phones the size of small bricks. We survived grunge (barely), witnessed a 70s comeback (no thanks), and shirked off our over-generalized Gen-X moniker. We weren’t fragile unique snowflakes, but we didn’t aspire to be our parents either, and it would take a new generation of upstarts to fix the mistakes we initially made with the internet (remember the epic implosion of 2001? My unemployment checks sure do) and show us that everything we were taught to believe about work, success, and life, was far from gospel.

For seventeen years, I worked in an office. I did what I’d been told to do or mimicked generations past — I worked hard and paid my dues, knew my place in the hierarchy and adhered to it, and believed an Odyssean commute and a matching 401K were the “only way”. I never conceived of a career outside the confines of a cubicle until I learned that corporations couldn’t guarantee a safety net or protect you from market and industry volatility, and even though you were constantly reminded of your value and worth during the annual corporate retreats and holiday potlucks, your livelihood was predicated on a P&L. You were only as valuable and indisposable as a company was profitable. You existed for as long as a company could bear the weight of you.

In 1997, I graduated college with a plan: work in finance for 10–15 years, get married, have kids — the whole whitewashed nine-yard. Just stick to the plan, I told myself because this singular version of a dream, one that had been photocopied by multitudes, was the only way. Right?

Until I learned that I loathed finance. You could be good at something and still cry in bathroom stalls. My work didn’t challenge me, the dress code (yes, back then we had a suit dress code with only Fridays as a reprieve) was daunting, my coworkers all hailed from the same Northeast schools, and I became curious about this “Internet thing”. I spent nights and weekends navigating AOL and dial-up service (remember when no one could reach you because you were online? Good times.) and using my financial and accounting skills, I launched a small business where I bought designer clothes and accessories from outlets and samples sales in New York and sold them online. I did this successfully for two years, but still didn’t believe in the safety of going out on my own. I’d relegated my business to a side project, that thing that would steer me away from finance and I could mail my paper resumes to new companies in new industries. During this time, I managed to fit in getting my master’s degree in Fine Arts — the antithesis of my “safe” Bachelor’s of Science degree.

My plan in 1997 was a graft that didn’t take, an implanted organ rejected by its host. My views on marriage shifted — I cared less about the white dress and the fanfare and confetti and instead wanted a partner, regardless of the paperwork. I also realized that I didn’t want children, which made marriage at the time a trickier proposition. Instead, I wanted my career and my novels. I worried less about the whitewashed life and figured that a partner would eventually materialize.

By 2013, most of my views of success were usurped. Millennials annoyed me initially with their impatience toward hierarchy and their seemingly abnormal professional velocity. There seemed to be an urgency in this generation that hadn’t existed previously. I kept thinking know your placeuntil I began to wonder what is “your place”? I was reminded of how I hated being silenced in the room when I had good ideas simply for the fact that I was under 30. I wanted to work hard, true, but I also wanted to contribute and be respected even if I hadn’t yet gone gray. I’d spent time around smart and creative millennials, who had great ideas and worked hard, but believed one could take control of one’s success, that one’s identity was not inextricably bound to their title. I saw them leave and start their own ventures and at first, I was shocked (though mostly afraid), but that fear turned into envy because I thought: I could do this too. So I left a job that made me unhappy to venture out on my own.

At first, I thought, oh, I’ll probably consult for a few months and get a job. Fast forward three and half years later.

There are hundreds, if not thousands, of articles that will instruct you on how to be successful as a freelancer. I’m not here to add to that noise, other than to say yes, it’s important to discern if this kind of work is right for you as opposed to being seduced by the glamour of working from home (it’s not glamorous, rather, it’s often isolating), getting experts like bookkeepers and lawyers are tantamount, and being smart about your offering and value proposition (i.e. what you do and why you do it better or differently than the freelancer down the block), know you have to have multiple projects going as a hedge and you have to always be pitching, closing, etc — these are all important and elucidated elsewhere in excruciating (and necessary) detail.

I turn 41 this weekend and it took me a really long time to be okay with not having a plan, of playing the days as they lay. That I’m not a failure because I didn’t cleave to what I had thought defined one’s personal and financial success and realized that definitions aren’t binary. That you can fail and fail better.

Sometimes I look at my peers or those who are younger than me and I think: they have it together. They bought a house, they live debt-free, and their life isn’t an artful navigation of student loan officers, creditors, and creative accounting. And for a moment I step into that comparison trap and before the claws snap I fall back. That’s their life, their definition of happiness, their path — not mine.

Would I love to be out of debt? Absolutely. Do I regret going to a fancy Ivy League school for a graduate degree when I could’ve saved money and gone somewhere equally good and local? Sure. But right now, right this moment,I have a business that makes me jump out of bed in the morning, I write the books I dream of writing, and I’m healthy (finally), sane, and the things I want will come…eventually. Right now, I focus less on a “plan” and more on living the best and most mindful life I can live. Right now, I focus on giving back and using my privilege to help others. Right now, I focus on living.

I read this quote today (I’m not a fan of Kerouac, but felt it appropriate):

And I will die, and you will die, and we all will die, and even the stars will fade out one after another in time.

You could look at it and think, that’s morbid, or you can view it as a call to live.

some thoughts on professional etiquette because some of you really need it (part 1).


People, we need to talk. About your etiquette, or lack thereof. I’ve been in offices for over twenty years, and I went from an intern who filed papers in metal cabinets to an executive who built businesses and lead teams. I graduated arrogant and over time I became humble. At the beginning of my career, Morgan Stanley sent me to “listening classes” and now I’m the sort of person who simply doesn’t listen just to wait for my turn to speak. I went from ferociously networking to becoming more strategic and thoughtful about the kinds of people I wanted in my life. I used to work with the crazies and now I’m too old for the hysterics. Although I started my career in an environment where the internet was a novelty and have since adapted to the rhythm and pace of what people term the “digital age,” there’s something to be said for good old-fashioned etiquette, because technology is not an excuse to disrespect people or waste their time. If anything, we live in an attention-deficit economy, and the more you create value for yourself and others, the more you’ll prosper.

Since I’ve become a consultant, I’ve had to contend with income instability (love that deal flow), expensive health insurance costs, but I also have control over my projects, can run my errands on a Tuesday morning, and can spend time with the people who matter most. This life has made me abundantly present, and as a result I’ve become more aware of wackness. There are many people who are not acting right, and I’m planning a series of brief posts on professional pet peeves and business etiquette.

Also, the cookies I made for the blog post I intended to write for today didn’t turn out that great, so there’s that. Instead of cookies you’re getting gospel.

1. The Very Nebulous Pick Your Brain/Be My Mentor Request: Can I pick your brain for 3 hours and 15 minutes in exchange for a $2.19 cup of coffee? I want to figure out my life! You seem to have it figured out, even though we’ve only met once! Then, can I milk you for all of your LinkedIn contacts? Then, can you mentor me? I can write a whole treatise on the ubiquitous “pick your brain” requests and why so many people are failing miserably. Let me pause here and say that although I’m an introvert who prefers to reside in the confines of my ultra-warm apartment (would you leave in 1F temps?!), I have lunch or coffee with at least one person a week whom I mentor (formally or informally). These are people with whom I have a vested relationship–they’re either former colleagues or people I admire in some way–and I know how they think and work.

My mentor lives by this axiom: Be brief. Be brilliant. Be gone. When I receive vague requests or long-winded emails, it tells me you haven’t done your homework and you’re looking to me to fill in the blanks and assemble the pieces. It also tells me that you don’t understand that time is the most valuable commodity we know of. Every request need not be met with hours spent in a coffee shop. Sometimes all it takes is a phone call, a Skype session, or an email connection/gchat. I’ll always help someone when they send a brief email outlining specifically what they want. Don’t underestimate the smallness of a request because specificity will make inroads faster than me issuing a team of private investigators to decode your email.

For example: a friend (and peer) recently made a dramatic career shift, leaving one industry for a not-yet-identified other. The friend sent me an email asking that I connect him with people who might be able to help him. I was happy to do it but I didn’t know who would be of value, so I wrote back and asked for more specificity, and he ended up taking the path of having conversations with a group of smart people across various disciplines. He knew that being around people who loved what they do might inspire him on his path, and then at that point I could offer him a more specific connection.

In short, don’t waste anyone’s time. Offer to reciprocate in some way beyond the coffee (of which I always pay for, especially if the person whom I’m meeting is younger–I’m old-school that way, I suppose). Over the past few years I’ve experienced the value of reverse mentorship, and sometimes I’ll send g-chats or notes to people who were my direct reports asking about the latest technology, changes in Facebook algorithms or to get their POV on a cultural trend. Even if you don’t know how you can help someone, tell them what you’re good at and offer to recip down the road. Even if I don’t take you up on it, I think it’s pretty cool that you want to help me, or someone I know, too.

Also, realize that trying to land the most seasoned professional as a mentor may not be your smartest bet. While I can counsel people on strategy, business, management, leadership, there are a lot of things for which I’m not equipped to mentor. I’ve often forgot about what it’s like to manage a direct report for the first time, or navigate a shady team dynamic, so sometimes it’s better to find someone who’s been where you’ve been in the not so distant past. Someone with 3-5 years your tenure can be more valuable than someone like me, who may have 10-15.

This isn’t Moby Dick. Catching the big fish may not be the soundest strategy.

2. The Blind Intro: Hey, Felicia! Meet my friend, X. She wants to work in marketing and since you work in marketing, I thought you’d hit it off. She’s also looking for a job, FYI. Attached is her resume.

Don’t do this, ever. I mean it. Never do this. Are you listening? I don’t care if you’re my closest friend–I will end you if you send me a blind introduction. It’s the professional equivalent of a group chat ambush because no one is really thinking about the person who’s being asked for a favor, rather, they’re thinking of themselves and their own self interests. Blind intros put people in an uncomfortable position of fulfilling a favor they either don’t have time for or simply don’t want to do. No one wants to appear as if they don’t want to help, and blind intros capitalize on this social tension. Why put someone you respect in an awkward position unless they explicitly say they don’t mind blind intros?

People know that when I email them with an inquiry for an introduction, I’m not wasting their time. They know that I’ve done the legwork to assess how both parties could mutually benefit from the connection. In an email I outline the specific ask, share some details about the recipient of the favor (LinkedIn link, blog, etc), my assessment of the situation and how I think this connection could be valuable–if not now, but in the near future.

If I get a refusal I harbor no hurt feelings because I get it–my email is yet another to-do and sometimes people just don’t have the time. Also, I’m strategic about my requests and how often I make them. Quality > quantity, always.


3. The Let Me Scan the Crowd for Someone More Connected Than You: Felicia, it’s so great to see you! (whiplash ensues, neck resembles that of an ostrich). I want to hear everything that’s going on in your life (neckbrace now required), but first I have to say hello to X.

Recently, I tried to make an introduction between a good friend of mine and a friendly acquaintance, and the acquaintance had her sights set on a more attractive prey. The introductions were brusque, all eye contact avoided, and my friend, who had considered my acquaintance for a project, in the end decided against it.

There’s a special place in hell for people who are predominantly consumed by those who are “good to know.” People who want to be part of a specific crowd without understanding the appeal of a crowd or “It” person is ephemeral. Playing the long game is tantamount. Befriending people because they have integrity, are kind, smart, and honest should be valued above any perception of equity or popularity. In short, playing the cool kid game makes others feel demonstrably less cool, and how would you feel if you were ignored for the bright shiny object just beyond your reach?

When I was in my 20s, my first mentor was a man named Bob who spent the greater part of his career at AT&T. He was old-school, and was the first person to shape my career. He told me once that I’d better be nice to everybody. Stop and talk to the receptionist, thank the people emptying your bins, and be graceful to your direct reports simply because it’s the right thing to do. Be good to everyone because you never know when you might encounter them again, when the power dynamic might shift against your favor.

I don’t care about your blog’s popularity or if you were on the cover of a magazine or on some ridiculous 30 under 30 list. I don’t care that you spin with that VIP person or you know everyone worth knowing. If I can’t endure a meal with you I don’t want to know you. If you can’t look me in the eye, I don’t want to know you. If you can’t give the people I respect and admire the time of day, I don’t want to know you. If you’re with me and scanning the room, looking to better deal, I don’t want to know you. Because there are plenty of people like me who only want to surround themselves with people they respect, admire and trust, and feel that those feelings are reciprocated.

An extension of this, I’ve learned, is try not to be an asshole to people. I’ve learned this the hard way having burned some bridges earlier in my career and finding people from a previous life suddenly reappear in a present one. We’re all human and prone to bad days and rage-filled outbursts, but apologize for your mistakes, try to be kind, and make reparations when you can.

4. The I Won’t Respond Because Your Request is Beneath Me/I’m Way Too Cool for You: Over the past two years, I’ve received offers to help a startup build their Instagram channel or manage their Facebook page–even though I’ve built brands, businesses, and have been working for nearly 20 years. Do I give attitude or get all huffy? Absolutely not, because at least people have been kind enough to think of me. And if my pipeline is horrifying (this hasn’t happened yet, knock on wood), I’m not beneath anything to pay the bills. Often, people don’t know the extent of your service level or offering, so they’ll just send you whatever sounds like a fit for you. I always graciously thank the person for thinking of me, politely pass with specificity on the kind of projects I’m taking, and an offer to help find someone to take the lead. Not only does this help in terms of me paying it forward to other freelancers, but I’ve helped someone who was generous enough to extend me a potential project. Often I’ve received, as a follow-up, more appropriate offers because of my specificity and humility.

In short, don’t give attitude. Get over yourself. Don’t act like you’re above anything, because you never know when you may need the work and people always remember that one freelancer who had the TITANIC EGO.

5. The Failure to Thank: Nothing, I mean, NOTHING, enrages me more than ingratitude. This year alone I’ve helped two people secure big contracts and neither of them have said a word of thanks for the intro or for the sizeable project they acquired as a result of my connection. Always be graceful, always be thankful. If someone makes an intro, thank them. If someone gets you a project, thank them. Even if you didn’t take on the project, thank them. I don’t need a meal; I don’t need your gratitude tears; I don’t need a % referral–I just want to know that I didn’t recommend an entitled asshole. Send me an email with these five words: Thank you so much, Felicia!

Karma has your direct dial, people. Don’t feel like you’re entitled to connections and projects. Send an email, a handwritten note or a creatively-sourced cat image. I can’t believe I’m even telling people about basic Emily Post please-and-thank-you etiquette, but apparently ingratitude feels more like the norm than abnormal, and that frightens me.

Photo Credits: Death to the Stock Photo