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What Was Your Best and Worst Career Move?

October 21st, 2009 @ 5:24 pm

8 Comments

Categories: Best Practices, Board Management, CEO, CEO Succession, Classic, Compensation, Entrepreneurialism, Executive Focus, Hiring, Management, Strategy, Technology, Tips and Tools, Wisdom, Workplace

Tags: Professional Development, Career, Startup Companies, CEO, Management, Executive, Job Search, Career Lessons, Steve Tobak

Regret is a bitter pill to swallow. That’s why, in terms of your career, it’s a good idea to understand opportunities missed and mistakes made in real time. They don’t age well.

Unfortunately, when it comes to career moves, insight can be elusive. And the good moves can be just as perplexing as the bad ones. I’m not sure what’s worse: having one success and being completely unable to duplicate it because you don’t understand how or why it happened, or not facing the fact that you made a bad decision and blew it all on your own.

That why you really have to take a hard look at both the good moves and the bad for them to be of any value. To that end, here are my best and worst career moves and lessons learned. They’re amusing and insightful all by themselves, but in exchange, we’d all like to read and laugh at … I mean learn from yours. That’s the deal, okay?

Best Career Move

I graduated from college in 1977 with a B.S. in physics, but there were no jobs, my grades were so-so, and I had no idea what to do next. I was dating a girl whose father just happened to be chairman of a semiconductor startup. He drove a Porsche, showed me around his very cool company, and I was hooked. So I went back to school, got a master’s degree in electrical engineering, and the rest is history.

Lessons learned: I remember being really down because my career had hit a dead end even before it started. Still, I never gave up hope, probably because, for whatever reason, having a successful career was imperative to me.

So when the opportunity arose, I pursued it like a starving pit bull, which meant bugging my girlfriend’s dad about how to get a job in the industry, then getting the graduate engineering school to admit me part time (they wouldn’t admit me full-time until I demonstrated I could pick up my grades, which I did, bigtime), and on and on.  

Lessons Learned:

  1. Set your goals and don’t let anything stand in your way
  2. Pursue opportunities to the end, no matter the odds
  3. Trust your instincts - when they say go, you go and don’t stop until you get there, wherever there is

Worst Career Move

In 2000, I was a senior VP with a late-stage startup company when the tech bubble began to deflate. Instead of hunkering down and sticking it out, I left to take a CEO job at an early-stage startup in need of a second round of funding. That’s when the bubble really burst and we ended up shutting the doors just seven or eight months after I got there. Four years later, the company I originally left went public and, well, let’s just say I left a lot of dough on the table.

Lessons learned:

  1. The Value of Stick-with-it-ness,
  2. It’s way better to be the number two guy at a company with a good chance of success than the top guy at a company with little-to-no chance of success
  3. Early-stage startups suck (for me, at that stage of my career, anyway)

Okay, now it’s your turn: Best and worst career moves, let’s have ‘em!

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  •  
    1

    keb-1

    10/22/09 | Report as spam

    RE: What Was Your Best and Worst Career Move?

    My worst move was going from the telecommunications industry to for profit health care. I learned too much about the financial side and it challenged my integrity so much that I left after a year.

  •  
    2

    AnitaGen

    10/22/09 | Report as spam

    RE: What Was Your Best and Worst Career Move?

    My best career move was to become an independent
    consultant to non-profits. I work from a home office, set my
    own schedule and income, and have the independence and
    income I want. My "worst" career move was not doing it a few
    years earlier -- but the truth is that most of my my client base
    needed to catch up on technology first to be comfortable and
    have the capacity to benefit from off-site assistance.

  •  
    3

    andrew.

    10/23/09 | Report as spam

    RE: What Was Your Best and Worst Career Move?

    Best move was to leave a company where I had been for many years and become stale to go overseas and try my luck. Found lots of opportunity and career development.

    Worst was one of those overseas positions. Was headhunted into a major global multinational to set up a new division. When joined was told that my late entry type was valued as they had a problem with people joining from school and staying through to retirement. Problem with this was people became part of the culture and company found it difficult to innovate hence why I and others were being brought in. Was gone within 18 months and found out at exit that this was normal. Also reason for leaving was very standard. Could not handle a work environment where every decision even to change the brand of pen used in the office was overseen by at least 2 committees. Also it was all very nineteen fifties public service in that you could not talk to people too many grades above you and even where you sat, the size of your office, did it have curtains or a chair for visitors etc was determined by your grade.

  •  
    4

    NicoleinON

    10/23/09 | Report as spam

    RE: What Was Your Best and Worst Career Move?

    My worst career move was made, fortunately, just a few years out of college. I moved to Connecticut and began working at a local AM radio station, as it turns out for an insane general manager who made me appreciate for the first time how abused wives must walk around on eggshells trying not to set someone off. I then cluelessly jumped from the frying pan into the fire working for the local newspaper, taking a hefty cut in pay (seemed worth it at the time!) The manager of the team quit shortly after that and I was, despite being the newest team member, the one most qualified to run the department, in the sense that Sarah Palin in a room full of third-graders is the most qualified to be President. I didn't know the job well enough and had never been a manager and my boss was dishonest, condescending and just downright incompetent.

    My best career move was when I decided I wanted to live in a free country again and I chucked it all in & move to Canada, where I got a job far more quickly than most immigrants, at better pay than I was making in CT, even taking into consideration the value of a weak loony at the time (hey, my checking account balance rose 25% when I moved the Merk money up here!) and I was able to get rid of my car and get around via public transportation. Today I have a *better* job with more money and lots of surplus cash at the end of the month that isn't being sucked into a four-wheeled wallet monster. It's also nice not having to worry anymore how I'll pay for it if I get sick.

  •  
    5

    Tricia21

    10/23/09 | Report as spam

    RE: What Was Your Best and Worst Career Move?

    My worst career move was not pursuing my writing career as I wanted to do coming straight out of university. I came out of uni with student loans, rent and other bills that ALL needed to be paid so I went into a field which neither inspired nor interested me and after a while began to drain my energy and sense of confidence in myself. Over the past 5 years I've switched jobs 4 times in the same field and have just found myself sinking deeper into the same pit. Also, the money I was making was being sucked into bill paying - so on top of not enjoying my job, I was not enjoying life!
    My best career move I've made is still ongoing - last year I decided enough was enough! I started actively pursuing freelance writing opportunities which brought back my sense of creativity sorely lacking in my other jobs. I'm still holding down my current "day job", but it's great to have some creative writing to look forward to doing and I intend within 1 year for this "day job" to be my last and to get full time into my freelance writing. And the money? I've stopped worrying about that and downsized my life considerably! So hopefully I'll soon be able to live the dream - enjoy my work and life too!

  •  
    6

    Tiaaguilar

    10/23/09 | Report as spam

    RE: What Was Your Best and Worst Career Move?

    I'm the model for "did I make the right career move?" I
    was working for one university and things were going well
    in admissions. Then I had a serious family issue I needed to
    relocate for to find some resolve. I took that promotion with
    that university-biggest mistake of my life and career with
    this university! I'm truly disappointed. The manager was a
    wackjob, bipolar lesbian and you never knew what
    personality you were dealing with, the employees were the
    worst I have ever seen. From day one I was told don't trust
    anyone. This was even a poster one employee made and
    had posted on her wall of her office! What does that say
    about a company? Not a positive environment. My family
    issue resolved, I quit my job, sought legal consultation for
    sexual harassment, filed a wrongful termination suit and
    moved back to my original city. Taking a job with another
    university in admissions whose manager, well, I think she
    just knew people in high places to get hired because she has
    not idea how to manage people and definitely has no idea
    how to train people. Honestly, I am going to look for outside
    sales position and get out the education field.

    Why don't companies invest in training managers how to act
    and treat employees? It does cost an organization a lot of
    money for training and rehiring. Why can't managers
    recognize talent and nurture that talent instead of treating
    employees like disposable commodities.

    I earned my degree in business management and am almost
    finished with my MBA, I want to teach management courses
    and return to outside sales. I'm so disappointed in my
    decisions and have a lack of trust about transitioning again.

  •  
    7

    sgiles3

    10/26/09 | Report as spam

    RE: What Was Your Best and Worst Career Move?

    @ Tiaaguilar -- I wouldn?t despair? I started my professional career in enrollment services and from what I learned ? turn over is always high. As a matter of fact, it was mentioned to me that if you wanted to ever get your just due salary in that profession, you HAVE to relocate or change careers. I was in the same situation, except in my office we had consistent managerial changes ? 3 years and 3 different managers. Ugh.

    Anyway, outside sales is always one route or you can continue your career in higher ed. Most Universities make money thru tuition (admission office), royalties (R&D/technology transfer office), foundation gifts (alumni relations office) and grants (office of sponsored research/gov?t relations office). With your MBA and admission experience, you are poised to make a smooth transition. I?m currently in tech transfer and credit much of my transition to my admission experience.

    Good Luck!!

  •  
    8

    R. B.

    10/30/09 | Report as spam

    RE: What Was Your Best and Worst Career Move?

    My worst career move was staying in an environment where I wasn't valued, appreciated, or allowed to be involved and where the person I reported to was abusive (verbally and in the way they back-stabbed and undermined me). I was treated like an enemy and every comment I made was belittled. I was frequently screamed at for making a suggestion, even though I was always careful to be extra respectful. I was treated so horribly, looking back, I can't believe I stayed as long as I did. It affected my health, self-esteem and confidence. I started doubting myself and felt totally worthless.

    My best career move was getting out of there.

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