An Ode to The Career

A Long-form Ditty

Photo Credit: Bates Communications

What do you do?

It’s a seemingly simple and innocuous question. But it also immediately frames you as a person; a potential pigeon hole if you will (that you didn’t necessarily ask for). There is rarely another opportunity in life for a response that starts with “I’m a…” to have so much impact or influence.

The answer to said question can range from very simple to overly complex. I’ve gone through periods where I had no response to the question as well as periods where my response was so long I never finished before the topic was changed or the woman walked away…

For me, one problem is that while I have done plenty of debate and public speaking, my elevator speech has been my nemesis. I either don’t know which one to give (see my background below) or never have the time to get all my shameless promotion in. I either need to pick the right elevator speech or find a taller building to ride an elevator and wait for someone to ask me “about me.”

Additionally, it’s getting increasingly harder for anyone to answer this query with brevity/uniqueness given everyone (at least here in the San Francisco Bay Area) is an entrepreneur of some sort or the “CEO of something” in addition to their regular “job” — irrespective if they are actually qualified or talented enough to do “CEO work”.

I’ve always been tempted to answer “What do you do for a living?” with what comedian Rodney Dangerfield said to a heckler (below) during his act but I never had the proper “liquid foundation” at the appropriate moment.

The greatest of all-time gives the perfect response…

I think the issue for me has been no one can get to know you in 5 minutes and to be judged for where you are getting your “full time” paycheck is silly — as if it is the only thing that defines you. Which is why some of my hobbies and personal interests have bled into my professional life. Either way, I hate to be put in a corner.

What’s in a Name?

All of this gets to the underlying theme of a “career” and what exactly that means. Yeah, yeah I know: Cue the standard thinkpiece insert:

Webster’s defines career as “a job or profession that someone does for a long time” or more explicitly defined — “a field for or pursuit of consecutive progressive achievement especially in public, professional, or business life; a profession for which one trains and which is undertaken as a permanent calling.”

My response to that definition is “Who gets lucky enough to have one of those? A Calling? Are you kidding me — who are those people??

Yes, apparently there is a large continuum out there for “career” definition— here is a sampling I was bantering about with a friend the other day:

  • Old reliable: The person who spent 30 years at their local big company; maybe it was even in a “one company town.” Never caused trouble, well adjusted, gold watch, pension, thank you very much…
  • The tradesperson — Spent their life learning a vocation, was very good at it and since the skill was always in demand — they had a nice living in an honorable profession.
  • The professional job-hopper: Always looking for the latest edge; Values experiences and self-worth; move up or move out mentality (I know someone who has worked for all four of the “Big 4 Accounting & Consulting firms #Masochist #WhyBother).
  • The “Love what you do; Do what you love” types: Über idealistic, happy — but not as happy as they appear (hey, they have to keep up appearances that they live by the mantra), and they stay up too late & watch too many infomercials (I tried to read that linked article, but gave up after the Namaste vibe overwhelmed me).

Obviously the above is not a comprehensive list, but notwithstanding Webster’s view (and the cheeky views above) — who REALLY gets to define “career” — You? Your family? Your boss? Random HR person? Society at large? Yes, they all have influences — but who is more important? And…who gets to say which definition or influencer is correct? At least Romeo & Juliet knew what they wanted…

My Resume? Is there a page limit?

I have a lot of professional irons in the fire and a few too many personal interests competing with those professional irons — but safe to say the common thread through it all is “advice.”

Save for a tour as Professional Services leader for a Silicon Valley Mortgage Technology Company, my main resume experience involves 20 years of advisory management consulting experience. I’ve gone from small boutique firms to the Big 4, to (in the last several years) independent work — I moved on (like the job hopper above) every few years for a variety of reasons (compensation, career advancement, company dynamics, boredom, etc.).

But I did (and still do) believe in my mantra: “I’m here to help.”

When answering professional queries, it usually was good enough for most people if I say “I’m in the consulting business.” It got more complicated when I further explained the many types of consulting disciplines in which I worked (and the “pigeon hole-ness” that goes with them — none of which are entirely true). Examples include:

  • Process Improvement (“Oh, you’re a rigid analytical guy” — sorry, have you spent 5 minutes with me?)
  • Financial Services (“So you’re a numbers guy” — Sorry, MBA School was 17 years ago, I forgot everything)
  • Change Management (“oh, you’re a soft skill guy” — I almost threw someone through a table for that one)
  • Strategy (“ah, a big thinker, no substance” — I kind of like this one. See video below…)
A typical consulting strategy

When I then include the fact that I’ve accumulated both a Real Estate Broker License and more wine education & certifications that I can keep track of, my party conversation/elevator speech starts to feel self-consciously longwinded and then guilt feelings creep in for doing those things.

I was torn since I’ve always been the person that people come to for advice, ideas, counsel, etc. I like consulting/working with clients and I have a passion for real estate & wine — why not make it all work somehow? How can I dispel the negative perception and still parlay all those interests and skills?

Why am I the way I am?

I grew up in Delaware (Yes, Delaware — famous for tax-free shopping, Joe Biden’s Senate career, and Ryan Phillippe). At the time I grew up in the 70’s and 80’s, Delaware (or at least my world within) was still very “traditional” from a career definition perspective. The message was: “Get a steady job, don’t cause trouble, retire, and get a pension.”

To illustrate, one Grandfather worked at the Chrysler plant until he “had to” retire with his pension and the other Grandfather worked his entire post-military career at Dupont until retirement & pension (The latter is now 91 and has been retired & receiving his pension longer than he actually worked at DuPont. My hero!).

But somewhere along the way, the idea of being non-traditional appealed to me. I worked (out of necessity) at just about EVERY GIG possible while growing up & going to school — I was a paper boy, pizza delivery guy, tutor, DJ, actor, lifeguard, and tennis coach (None of which were a “calling” unfortunately).

Maybe I was too much of a romantic, and idealist, or just watched too many movies — but in my post-college life I went for jobs that expanded my breadth of experience, not necessarily the depth — which, depending on which HR person you’re talking with, can be a blessing, a curse, or a bit of both.

Meet my friend — The Gig Economy

Have you claimed ownership of any of the “titles” above?

The Gig Economy has been a counterpoint to older perspectives and somewhat of a bridge to the newer perspectives. It has augmented the overall knowledge economy and, at least in larger cities, is responsible for an increasingly larger percentage of knowledge workers.

But the perception from the “mainstream” career makers (e.g., Big Company HR) is still mixed if you say you’ve done any of what is in the photo above — as in “Why did you NEED to do one of those if you just had a full-time job?” — as if there is no discernible difference between “need” and “want.”

For me, the gig economy has been great. Initially, it was a bridge from leaving a full-time role but became more of an affirmation of the “worth” of my skills, experience, and aspirations. It has also introduced me to clients and industries I may not have worked with otherwise, offered experiences I didn’t have previously and paid a more premium rate than an equivalent full-time role would (Albeit at the risk of not billing full time).

Shameless Financial Sidebar: Look — great full-time roles do not grow on trees — especially those that include both a suitable work environment and competitive pay package (aka — the pay trifecta: Salary, Bonus, Stock). Contracting (aka, Gigging) is more flexible from a schedule perspective and can be much more lucrative if you bill full time (even more so than doing the same full-time role) and can get your health benefits elsewhere (spouse, trade association, etc.). So the Gig Economy track is both an honorable lifestyle as well as a suitable alternative until that tree starts blooming with full-time jobs.

Still, for someone of my generation — going back and forth from the gig economy to a full-time position at a large company is not as accepted in the traditional sense.

Have you ever filled out an HR form for a background check where they ask for “7 years of employment” history? It can be a day long commitment if you’ve had enough clients.

The perception is that someone of my age should have a linear progression instead of more iterative career path or goals — irrespective if the latter actually makes me a better person or asset (from the company view). It seems kind of silly to justify utilizing your skills, adding value to clients, and making a premium salary to then have an HR representative throw up all over it.

This is the common (mis)perception of the Gig Economy

Alas, sometimes the gig economy is no bargain either. In addition to the perception issues, there are these lovely drawbacks:

  • Non-guarantee of “full-time” hours — so even if the hourly rate is a premium one, if you don’t work “40 hours per week” the rate is less of a bragging in a bar proofpoint.
  • There are instances where you have to work through a 3rd party, which lowers your “take.” Some 3rd parties are great — owners of small consulting firms who have their shit together and are fair to their subcontractors. Then there are the “body shops” who operate on “small” margins (since they pay “smaller” as well). Think of it as a pimp-like relationship since they add no value other than getting you in there and funneling the cash.
  • You sometimes work with partners that you cannot control and, add to that, You have Less than Zero* percent of the leverage that a large consulting firm would have with the client (i.e., you just have to sit there and take it when the client won’t listen to you, or puts away the presentation you worked for months on — knowing full well they will never look at it again).

The Influencers & HR Myopia

At another end of the spectrum, there are people that do 4–5 different things and that is perfectly fine in some societal circles. Here are a few profiles to review in case you’re wondering:

Gary Vaynerchuck

Chris Brogan

Guy Kawasaki**

These gents above do eleventy billion different things and are considered “thought leaders” or “tastemakers” or as Linked In calls them, “Influencers” — because they have achieved some notoriety.

These guys end up in Inc. Magazine (Well, maybe a bad article example, but hey, it’s my thinkpiece) while I sit and over-explain/apologize to an HR Generalist why I am part of the gig economy and spinning up a few businesses? I am calling BS on that.

And what happens when “not so famous guy” (or at least not as famous as I thought I was) attempts to have many non-traditional arms in lieu of a traditional career?

Well, the answer is it usually doesn’t go over as well or isn’t as readily accepted by the majority. Sure the people who get it, get it — but the random company HR person — the one is trained to look for formerly traditional items like “XX years doing the same thing in progressively higher org level capacity” is absolutely lost when encountering someone like me if I am not an influencer on Linked In.

*Shameless Financial Sidebar #2: The dreaded “What are your salary requirements?” question from random HR person for a full-time role. They never like the answer — and this is the ultimate irony. You tell them what you’re making at your “gig” and their response is usually, “oh, we can’t pay that for this role” (Well, at least you know you didn’t leave money on the table). That “career” role, I might add, usually includes 50% more hours and commitment than your gig does. They thumb-nose your gig but hold with endearment their more work, less pay “career opportunity.” Morons!

Going Establishment — A Cautionary Tale

Look, it’s like they say, if you’re not a rebel by the age of 20, you got no heart, but if you haven’t turned establishment by 30, you’ve got no brains. Because there are no storybook romances, no fairy-tale endings. So before you run out and change the world, ask yourself, “What do you really want?
— Buddy Ackerman (Kevin Spacey) from Swimming with Sharks

Recently I had the opportunity to (re)explore the magical world of Big 4 Consulting (First tour of duty 2003–2006). Yes, the world of big billings, fat expense accounts, 7 days per week attached to a computer, and a lower than expected bonus was but a few interviews away. Some of my former colleagues encouraged me to give it another shot at a different firm — and I initially liked what I heard — clearly there must be a catch?

And then…

After flying all over the country for (seemingly 400) interviews with top partners and doing well, I flew to meet with the head of the practice I was to work for…during Christmas week…in a cold city…only to have my resume (aka — Career) “progression” questioned:

I’d actually prefer this method…

“Well Dan, you haven’t worked at a Big 4 in a while and I am not sure how that would be for you.”

Really? What am I, 10? Was this my first interview ever?

Perhaps they thought I forgot how to do the job I was hired to do (at the same level) 13 years before at a different Big 4 — and had been doing since, just not at a Big 4? This was not an issue for all the others I met with during the process, but at that moment it seemed as if the person in the room was waiting for me to apologize for the choices I had made and admit their way was the best way.

I wanted to throw up — not necessarily for the statement that was made to me (Although I am fucking tired of justifying my career path to small minded people), but for the fact that I actually thought it would be different this time (There was a reason I left a Big 4 firm the first time). All I could think about was what time my flight was leaving to come home.

PSYCHOLOGICAL SIDEBAR — I think that, no matter how cool we are or want to be on our own, there is still that allure to being at a big firm. We all want to feel like “we’ve made it” and that we are important — and that importance can be exemplified with the opportunity to be “partner” at a Big 4 firm. For me — call it ego, proving something, or even “settling” — I wanted one more run at that life and I decided to go for it.

But that’s the thing — it only takes one. It takes one person to show you how you’re selling out your ideals for a paycheck or an ego trip. It only takes one person to remind you that you’re full of shit if you talk one way, but your actions are another.

And it only took one person to remind me of this: ”Just because others have a small mind, don’t assume that I do.”

I felt dirty & I couldn’t wait to get out of there.

La Verdad

The simple truth is — there is no right or wrong way to define one’s own “career.” It’s entirely up to the individual — and the only one who matters is the one looking back at you in the mirror.

So, if you’re like me (or how I have been) — on the edge of craziness because you’ve spent time in interviews or meetings having to explain why you’re doing what you’re doing, being made to feel less than you are, or being talked down to by someone less experienced than you are — then I have a new perspective for you.

Seriously, there is already enough self-loathing that happens (at least in the consulting profession) without being made to feel like you’re not “being all you can be.” I’ve spiraled in enough mundane work for clients (and I know what a spiral looks like) who either don’t want you there, won’t use what you produce for them, or ignore what you recommend for them.

The true identity killer for me was that I was starting to apologize for who I was — in all aspects of my life. So you know what I did?

I stopped apologizing. I’m taking the Tom Cruise perspective from the movie Magnolia.

If Tom Cruise said it — why can’t I?

I realized it is ridiculous to apologize for what I know, what I have done, and what I want to do — especially to people who don’t understand, cannot compromise, or are too fucking myopic to do either.

It was time to either do things on my own or if I partner with others, partner with people who get it…and, as a horse racing fan, I like to think it was a fine time to start “betting on myself.”

The new “About Me”

“This is not the old me…this is the new me…”

So, yes — I have multiple things that I do, am happy to be doing them, and I do them pretty well. Why be penalized because I have a basket of knowledge, skills, and interests that I want to focus on instead of being defined by just one? Think of me as a 2016 “Jack of All Trades” if you will (which means it’s ok).

I will no longer shy away from the “What do you do?” question for fear of judgment or ridicule . I accept that I am what I want to be & I know where I want to go. Do I call what I am discussing a “career?” I don’t know — To be honest, now that I’m thinking about it I usually associate the word “career” with the past. I’m looking forward.

So, shall we try it?

What do I do?

Well, I still give advice…but I do it on my terms without worrying about how my “progression” appears or chasing the approval of the HR community.

My elevator speech is now “I consult, educate, and make deals in the Financial Services, Real Estate, and Wine industries.”

Assuming you’re hooked a bit, I can explain further:

1. I recently joined an investment banking firm as a Managing Director helping with business development and deal oversight. If you need help (or know someone who needs help) with financial advisory services such as raising capital or Mergers & Acquisitions, contact me at and read about the firm here.
2. I am a licensed Real Estate Broker in California & have my own boutique brokerage company focusing on buyers and investors. Contact me at for your Bay Area Real Estate needs and you can view the website front page here.
3. I am a multi-credentialed wine educator & consultant. I partner with another wine educator to present and conduct seminars at conferences, corporate events, and personal gatherings. Contact me at for more information on service offerings and bookings and view the website front page here.

And…yes, since it’s impossible to get away from my early mantra of “I’m here to help,” I still do the occasional contract management consulting!

Connect with me on Linked In & I‘ll be happy to discuss how we can collaborate and how I can help you whatever your needs may be.

Now, pouring all the above out in this thinkpiece doesn’t mean I won’t be into something different next week either — but as they say “It’s my life” and yes — also my career.

So…now the question is…

What do you do?


*Robert Downey Jr’s most underrated role as “Julian” in Less than Zero

**Sorry, but anyone that leads with “evangelist” cannot be taken seriously and is lucky they don’t get beat up regularly

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