Early in my career, I made an embarrassing mistake.
I'm not proud of it. In fact, I still shudder when I think of my arrogance and cluelessness. But, like most mistakes and wrong turns, it taught me lessons that have helped ever since.
It happened more than 30 years ago, when I was in my mid-20s. As part of my work-advice series, I'll tell you about it.
It began when I realized that the "adventurous" career path I had chosen after school was no longer working for me and that I needed to look farther ahead than the next 12 months. It involved a well-researched and well-considered decision and then a hasty, uninformed one. It culminated in a humiliating dressing-down by the famous and controversial TV anchor Lou Dobbs.
It's not a short story. But it contains other career lessons, too, so I'll share the full context. Thank you for reading! And if you're just here for the part where I get schooled by Mr. Dobbs, scroll down to "Lou wants to see you"…
For years I 'followed my bliss'
Back in the early 1990s, I was four years removed from Yale University. My career to that point had been, well, improvised: I had taught English for a year in rural Japan and then taught tennis in San Francisco to pay the rent while I wrote an unpublished (unpublishable) memoir about my time in Japan. I did stints as a freelance reporter for a tiny newspaper in Massachusetts and fact-checker and proofreader for magazines in New York.
I didn't regret those choices, and they hadn't been difficult ones to make: I had done what I thought I was supposed to do — "follow my bliss."
Unfortunately, I didn't yet know that "follow your bliss" is actually bad career advice. I also didn't know how little I still knew about the "real world" — the world of work and life — as opposed to the world of school. Of course, not knowing much about the real world hadn't stopped me from developing rigid views about what was wrong with it and how it should work and what my place and purpose within it should be. These views included which jobs and careers were acceptable and which were, well, selling out.
"The world doesn't need any more lawyers or bankers," I told myself. So, whatever I did, I wasn't going to be one of those.
I was, of course, hardly the only recent college graduate who still had a lot to learn, but my idealism was particularly stubborn. And, in any case, by my mid-20s, my choices had led me to a challenging spot.
The theory underpinning "follow your bliss" is that, if you do what you love, the money will follow. I had tried that. But it wasn't blissful. And the money definitely wasn't following. I didn't love freelancing — I found it lonely and difficult, and I wasn't as gifted or accomplished a writer as some of my peers. And always being broke was making my life increasingly unsettling and difficult.
By now, my peers were doing things like getting promoted, going to grad school, buying cars and apartments, and getting married. I was still living out of a duffle bag and schlepping between sublets.
So I started doing what many of my college friends had done much earlier: researching the world of work and careers and trying to figure out what I wanted to do.
To be fair to myself, I was also dealing with a tragedy. When I was 25, my mother was killed in a fire that also destroyed our house. I didn't think the family stuff was affecting me — it didn't feel like it was — but one of the many lessons I learned in this period is that you can't always trust your feelings. In hindsight, I was a mess.
You want to work on… Wall Street?
My discomfort with living hand-to-mouth led me to consider many possible next steps, including an industry I had sworn off: finance. My dad was a banker, and I knew a lot of people who worked on Wall Street. Also, despite the fact that the world didn't need more bankers, there seemed to be a lot to say for being one.
For six months, I did my homework. I read and learned everything I could about every path I was considering. Surprisingly to me, the more I learned about Wall Street, the more excited about it I got. The industry seemed fast-paced, fascinating, entrepreneurial, and fun. It also paid well, an attribute that I found increasingly attractive.
So I began to take the idea of working on Wall Street more seriously.
Of course, a lot of people want to work on Wall Street — including a lot of well-qualified people who have been preparing for years to work there — so Wall Street jobs are hard to get, especially when you have no relevant experience and know almost nothing. Getting in the Wall Street door also required skills that I had yet to develop — such as making a compelling pitch for yourself during a job interview. So, in addition to learning the basics of finance, I had to learn how to do things like network, dress for success (or at least for less embarrassment), and present myself and my "experience" in a way that might make people actually want to hire me.
All of this was challenging. Not surprisingly, most firms rejected me sight unseen.
And when I did finally manage to get an interview or two, they were short and perfunctory. Aside from formulaic ding letters, I never heard back.
But an interesting — and telling — thing happened. Instead of being deterred or demoralized by this endless stream of rejection, or concluding that it was preposterous to think that I could or should ever work on Wall Street, I got energized by it. Suddenly, I really wanted to work on Wall Street.
Learning how to sell yourself is, of course, the most basic job skill there is, and learning how to deal with rejection and objections is part of it. If you can't convince a busy human that you will be helpful to them and their mission, better than all the other people who want the job, and worth more than they will be paying you, why would they hire you?
Anyway, over many months of networking, research, and interviews back in 1993, I gradually learned how to sell myself.
And you know what else I learned?
I learned that I liked the process of getting a job. It involved researching the industry, meeting people, figuring out what customers (employers) wanted, developing the product (in this case, me), and then selling it. That was fun!
(Later, not surprisingly, I gravitated to jobs that allowed me to do work like this for a living — building a following as a Wall Street research analyst, for example, and then building a company as the founder and CEO of Business Insider.)
The job-hunting process was so engaging, in fact, that months later, when I actually got a job offer in the research department of a bank, I wondered whether doing the job would be as fun as getting it.
But wisely, relieved to finally have not just a job but a salary — and telling myself that, even if I didn't love the job, I could do it for a while, learn some skills, and then decide what to do next — I accepted it.
My new career didn't last long
Unfortunately, and fatally, my Wall Street job didn't start right away.
And the several-month hiatus between my landing it and starting it left me a lot of time to think.
Having a lot of time to think, it turns out, is not always helpful for me. When I don't have an all-consuming, brain-occupying challenge (like looking for a job), I brood. And when I brood, I sometimes get lost in my own head.
While I waited for my Wall Street job to start, I brooded about the whole idea of working on Wall Street.
Wall Street might pay well, but it was the very definition of "selling out." It would mean working 70-80 hours a week. It would mean wearing suits and being trapped in hermetically sealed office towers. It would mean swimming with sharks, who might chew me up and spit me out. It would mean devoting all my waking hours, passion, creativity, and energy to making money.
Making money didn't seem like a worthwhile use of a life. And the world didn't need any more bankers.
Working on Wall Street would also put me on course to maybe suffer the same fate as my father — namely, eddying in middle-management, getting pushed out of his company mid-career, and then feeling like a failure.
This last concern didn't feel like what it was — fear. But, again, my feelings were leading me astray. It would not be until later that I realized that part of what was making me ambivalent about taking my next big career step, to Wall Street or anywhere else, was the fear that I, too, would fail.
I should have called the Wall Street firm and asked if I could start immediately. But I didn't. Instead, I kept brooding. And, slowly but surely, to the dismay of my family and friends, I talked myself out of the job.
Two months after accepting the Wall Street job, I called the bewildered research director who had hired me and told him I was going into TV news.
With my recently-learned job-procuring skills, I told myself, anything was possible. I could work in lots of fields — including ones that were better for the world (and a better fit for me) than Wall Street. For example, I thought, in a sudden and weird burst of inspiration, I could work in… TV news! TV news was journalism — an acceptable career for people who didn't just want to make money but also wanted to do good. TV news was exciting and glamorous. And TV news was even lucrative: TV anchors made a lot of money!
I, of course, knew even less about TV news than I knew about Wall Street. But never mind. I had found my new dream job.
So instead of proceeding calmly and open-mindedly through a run-of-the-mill mid-20s career transition, I threw a giant roadblock in front of myself. Two months after accepting the Wall Street job, I called the bewildered research director who had hired me and told him I was going into TV news.
Welcome to TV!
I knew almost immediately that I had made a mistake.
Not because TV news isn't an excellent career — it is. If I had taken the time to research the industry and its career paths, it might even have been an excellent career for me. I know this because, over the past 20 years, I've been fortunate enough to have done a lot of on-camera and production work, and I've enjoyed it a lot.
It was a mistake because I hadn't done my homework and didn't know what I was getting into. And also because, for personal reasons — which are real and important factors in career decisions — what I needed at that time in my life was not another prolonged, uncertain, and impoverishing job search but a stable and predictable job.
But, by then, it was too late.
Getting a job in TV news proved less fun than getting one on Wall Street. But many months later, after going through another networking and interviewing process, after learning that jobs in TV news are just as hard to get as jobs on Wall Street — and after asking for a referral from a well-connected friend — I managed to land a three-month internship at a New York-based offshoot of CNN called CNN Business News.
I was, of course, relieved to have finally found something — it made my decision to pass on the Wall Street job seem less idiotic. But the details were sobering.
The salary, for example, was less than half of the one I had been offered on Wall Street — with no benefits. Even after I moved from an intern to staff, it would be less than I had cobbled together as a freelancer.
And the hours?
Well, my shift started at 5 a.m. So I would have to get up at 3:30.
And the work?
Well, I didn't really know much about the work, because I hadn't done my research.
But at least I wasn't selling out.
Paying my dues
TV news production, at least in those days, was what might be described as an "apprenticeship" business. They didn't just hand you a microphone and fly you off to cover a war. Instead, as in many fields, you had to "pay your dues."
This process of "dues-paying," moreover, didn't take into account the ambitions of any particular employee — such as me — who might have preferred to pay all his dues in, say, an afternoon.
Instead, the typical career progression went something like this:
three months as an intern
two years as a production assistant
two years as an associate producer
two years as a "news updates" producer
many years as a "show" producer
After all that, if you were lucky, and had the face and voice for it, you might get a screen test and the opportunity to go report some stories.
I estimated it might take me five years to earn my way into the salary and benefits I had just sniffed my nose at on Wall Street.
And then there was the work.
Interns at CNN Business News were responsible for:
"Ripping wires" — monitoring the endless scrolls of news stories that got pushed out of printers, tearing the scrolls off, and rushing the ripped-off pieces to the producers (who would scan the stories and decide what was worth reporting).
Copying market and stock levels off quote screens and putting them in scripts.
Running up and down stairs delivering scripts to the control room and studios.
Scrolling scripts through teleprompters at precisely the right speed. (This was surprisingly difficult — you had to read along and listen to the anchor and make sure you didn't throw the anchor off by getting ahead or behind).
None of these tasks involved "getting coffee," at least. And they all had to be done.
What none of the intern jobs were, of course, was creative or intellectually challenging. And neither, it seemed to me, were the next jobs up the ladder. Rather, these jobs seemed to involve an unpleasant combination of intense time-pressure, painstaking logistical management, and kowtowing to the stars of the TV news business — the reporters and anchors.
Wait, this job sucks — and it's CNN's fault!
"Paying your dues" is worth it when you want the next job up the ladder.
Unfortunately, by the middle of my first week at CNN Business News, I had realized that I didn't want the next job up the ladder, or even the ones above that. I had also realized that none of the jobs up the ladder (or the one I had) included things I liked to do or was good at. So I would have a hard time matching the enthusiasm and skills of other dedicated interns and production assistants, who really wanted those jobs.
So I had to face reality:
I had walked away from a job that I had done my homework on, worked hard to get, and would have been a good fit for me… for a fantasy.
At that point, there were two mature courses of action, both of which required me to take responsibility for my decision and act like a professional.
Do a great job as an intern, learn as much as I could about the TV news business, and, ultimately, try to find a compelling place in it, or…
Do a great job as an intern, and — on my own time — try to find a job that was a better fit.
Unfortunately, I didn't do either.
Instead, I brooded. How could I have made such a dumb mistake and now have to do such boring work and get paid peanuts? Worse, I blamed CNN: I was a smart guy! I could do more than rip wires and deliver scripts. If CNN would only let me do real work, I could be out covering stories by now!
More importantly, distracted by my frustrations, I did a lousy job.
How?
Well, for example, when I wasn't busy with the tasks above, I sat at the intern desk and leisurely read newspapers instead of seeing what else I could do to help — in full view of the stressed-out producers.
I slept through my alarm and came in late. Twice.
I scrolled the teleprompter at the wrong speed, annoying anchors.
And I inaccurately transcribed numbers off the quote machine, causing an anchor to report that the Dow Jones Industrial Average was trading at a level that it was not, and, thus, misinforming viewers and hurting CNN's credibility.
These mistakes — and, I assume, my surly demeanor — soon got me called into my boss Lisa's office. Lisa was admirably direct — something I later learned is a hard but critical skill for a boss. She enumerated each of my mistakes and said that I needed to do better. She also suggested that I step up my energy level — after all, I was working in a roomful of busy people I might want to impress.
I told Lisa I would do that.
And then, despite being embarrassed at having been called out for my incompetence and bad attitude, I slept through my alarm and got the numbers wrong again.
'Lou wants to see you'
The next time I saw my boss Lisa was a day or two later, when she asked me if I had a minute. (Uh oh.)
"Lou wants to see you," she added.
Lou?
I hadn't met Lou, but I knew who he was. Lou was Lou Dobbs, the head of CNN Business News and the anchor of the premier nightly business show, "Moneyline." In later years, Lou would become a controversial Fox News host, but thirty-five years ago, he was a top business journalist. He was also a successful executive in his own right. Lou had built CNN Business News. He was living proof that TV news could be lucrative, at least for some people. Word on the intern desk was that Lou commuted into Manhattan from a horse farm in New Jersey and made $6 million a year.
Lou, naturally, had a corner office. My boss Lisa led me into it.
When I entered, Lou was standing behind his desk, dressed to the nines. Lou motioned for me to sit in a chair in front of his desk. My boss Lisa not only stayed in the office but, unnervingly, took a seat directly behind me — the same place a mob captain sits while waiting for the boss's signal to garrote a traitorous underling.
I wasn't a suit expert, but the one Lou was wearing looked like it cost a fortune. So did his shoes. I got to examine Lou's shoes up close because, after settling into his chair, he leaned back and put his feet on the edge of his desk, with the soles facing me.
If this feet-in-your-face alpha move was intended to remind me who was boss, it did. I was terrified.
Lou lifted a piece of paper off his desk. For an agonizing minute that felt like a century, he read whatever was on it. Then he put the paper back on the desk. Glancing down, with horror, I saw that it was my resume.
Lou put his feet back on the floor. Then he looked straight at me.
"I have a question," I remember him saying.
I was extremely ready to answer whatever question Lou might have.
"Why is it," Lou asked, "that a guy who graduated from Yale University can't transcribe numbers correctly?"
Lou let that question marinate in the air.
There was no good answer, so I began stammering.
Lou let me stammer. (He was a pro).
Then Lou asked me another question.
"Why is it that a guy who graduated from Yale University can't be bothered to show up at work on time?"
There was no good answer to that question, either. So I stammered some more.
It went on like that. Despite my stammering, I apparently did not answer Lou's questions to his satisfaction, because he asked me again, more directly, what I thought the problem was. And, stupidly, I answered more directly.
I talked about how I thought I could handle more challenging work than I was being given, about how I thought I could learn and advance faster…
Of course, we both knew what I was really saying.
What I was really saying was: I'm too good for this job.
Lou nodded. Now we were finally getting somewhere.
I kept talking. And as I listened to myself, I realized what an entitled asshole I sounded like: By suggesting that I was too good for the job, I was also suggesting that I was better than all of my hard-working colleagues — who, unlike me, were professional, competent, and eager to please, and busting their asses every day to pick up my slack.
Lou let me have my say.
And then he had his.
Lou's say, which he preceded with another prolonged inspection of my resume, went something like this.
"I can read your background in two ways," Lou said. "On the one hand, I can see a smart guy who has done different things and is just having a hard time getting going in life. On the other hand, I can see a checkered history — and, possibly, a character problem."
I was grateful to Lou for suggesting that, despite my slow start, I might still have a promising future. But the "checkered history" and "character problem" remarks exploded like bombs.
Instantly, the fantasy story I had been telling myself — that it was somehow CNN's fault that I was doing a crappy job — evaporated. And the truth was laid bare:
Regardless of how little I liked the work, regardless of how frustrating it was to have to "pay my dues" — I had chosen this job. CNN hadn't forced me to take it. If I didn't want the job, there was a line of people around the block who would fight each other for it. Any of those people would be more grateful for the opportunity— and be applying more of their energy to it — than I was.
By taking the job, I had implicitly promised CNN that, in exchange for the money they would be paying me, I would provide the high-quality and professional service that they expected and deserved. And, of course, because they were the ones paying me, they would get to determine what services they wanted from me — not me.
More broadly, I saw the tremendous privilege and good fortune that my education, parents, country, and friends had bestowed on me — and the responsibility that went along with it. I had more excellent career options than almost anyone else on the planet. So it was my responsibility to make good, informed decisions, own the consequences, and do my absolute best.
In other words, a job is a privilege, not a right.
And no one — least of all me — is too good for anything.
Lou finished his speech by saying something to the effect of, "we're not going to rearrange things around here for you, so get it together or work somewhere else." Thankfully, I had already decided to get it together. I got to work on time the next morning, and I made sure I got the numbers right. I also thanked Lou and Lisa for setting me straight. I'm still sorry I put them in a position to have to do that — that was my most embarrassing mistake — but I'm grateful for their candor. I also apologized to my friend who had helped me get the job. Eventually, I think he forgave me.
Lou Dobbs's version of the shape-up-or-ship-out speech was more theatrical than the one I would later use when I had to deliver the same message to people working for me. But, hey, TV is show business. And it was certainly effective.
A few weeks later, I told my boss Lisa that I would not be expecting or asking for a staff role when my internship ended. It's better to have a struggling employee quit than to fire them, so she was relieved. Lisa shook my hand and wished me well. And then, I assume, she picked the next resume off the stack of thousands of people eager to work in TV news and replaced me that afternoon.
After taking a break to screw my head on right, I resumed the course I had settled into before my detour: I began looking for another job on Wall Street. Fortunately, by then, I knew how to get one.
Mistakes are OK
So you see: You do not have to have your whole career and life figured out on day one.
As you try to answer the hard but critical question about what to do, you can — and probably will — take wrong turns and make mistakes.
That's ok.
Research helps. So, do your homework.
But the only way to really learn what you need to know to make good career decisions, especially the part that concerns you — what you like to do, what you're good at, and what really matters to you — is to actually do things.
You'll know when you're on the right track, because you'll like at least some of the work you're doing, and you'll feel competent at it. You'll want the next job up the ladder. And you'll be patient with the dues-paying, because you'll enjoy the journey.
And if you veer off course, the way I did?
Well, you'll know that, too. And as long as you learn from your detour, you will have a much better idea of what kind of job and career will be better for you.
And with the job-hunting skills you developed while taking that wrong turn, you'll be better able to go make it happen.
By the way, I'll leave you with another career tip: Paths often recross. So try to be good to people.
Seven years after Lou read me the riot act, when I had become a well-known Wall Street analyst, he had me as a guest on "Moneyline." And, later, one of the CNN producers who had handed me scripts to run up and down stairs, Diane Galligan, hired me to host a show for Yahoo! Then, still later, I hired Diane to build our video business at Business Insider.
Life can be long and strange. And we learn as we go.
So, go get 'em!
Send your work-related questions to askhenry@businessinsider.com!