Career Change – Ask and You Shall Receive


You will often hear me saying that fortune favors the bold. Even though I really believe this, and have experienced it first hand more than once, I was shocked with the results of telling my boss that, after a year of being the company’s sole Finance and HR person, I was not only not interested in going full-time, but wanted to do something completely different.


The Setting


Let me give you a bit of a background here: I had just returned to work after six weeks in Europe, where the boss let me work remotely. Six weeks. Full pay.

A year ago, I got the Office Manager job by agreeing to go full-time in 2015. I also said that, no, I would not get bored with the administrative work, nor want to go to PR (my Marketing Manager’s guess!) or anything like that.

In short: odds were slim that announcing my new career plans to the boss who hired me for administrative work, and whose business very much relies on my position, would go over well.

The odds of him giving me a job in my desired field that I had no experience in – at the tender age of 42 – were slimmer.

It was not going to be a smooth conversation, either. Sure, I have a truly great boss, but he is also a no-nonsense CEO and engineer, with a silent but definitive manner of conveying that you really really don’t want to make him unhappy.


The Bold Move


And yet, on the call that was going to be a formality in which I accept the full-time Office Manager position, I instead announced that I wanted to do something completely different.  I also told my boss that I love his company and would love to stay in a writing or communications capacity, if at all possible.

What do you think he said? 

  1. (sarcastic smirk) “Well, this comes as a surprise, but I can’t do anything other than wish you good luck” and, “What is your timeframe for leaving?”
  2. (nice smile): “You have to do what speaks to you”, and “Let me talk to our Marketing Manager and see if there is anything in-house for you”.


The Outcome

If you had asked me to guess, I would have gone for a). That is what I was planning for, and made the career change announcement  mostly as a way to start transitioning out of the company.


However, my friends:Fortune Favors the BOld

Four business days later, I was offered a part-time position as the Product Manager, creating all communications related to sales, messaging and positioning around the company’s product.

How crazy is that?

Now, you wonder, why on Earth am I telling you all this detail?

Because I know that there are so many of you out there who cannot fathom a scenario like this. Who believe that we are not allowed to make bold career demands, particularly at a certain age. Who don’t realize how much our workplace demeanor, loyalty and intelligence makes us highly valuable for ANY position.


How do I know? Because I am one of you!

The best outcome of the talk with my boss – an unlikely but decent one, I thought – was that he offers me a low-level, paper-pushing, event-planning job in marketing, taking two years to prove myself before I move to a position I really want…while underpaid and unmotivated to death.

Instead, I got a job in my field that I did not even know existed! A stretch job, yes, an uncertain job, yes…but a job in my field never the less!


What Made the Difference


That low-level marketing job that I would normally embrace with gratitude and see as a great entry opportunity? I had to work hard to prepare myself to say “no” to it.

I thought hard about what I wanted, and decided that, while a nice and potentially safer path, a position where I do things that bore me would be a waste of time and energy, and that I’d rather go elsewhere, or freelance.

Being prepared made it easier for me to say: “I want a writing or communications position”, which made it easier for my boss and the Marketing Manager to place me in the only position they had open.

I have since had two weeks of nail biting, little sleep, anxiety about what happens to the job, and whether I’ll succeed 


I rush to the bus every morning. My workday flies by. I am learning so much! I am a part of a great team. I find everything else in my life (except this blog) an absolute distraction and nuisance. I have to force myself to get away from the computer…see – I can’t stop writing about it even though all I really mean to say in this particular post is:


Fortune Really Does Favor the Bold


As I write this, I remember every successful career change story I heard about (many great ones here) and, let me assure you, it rarely involves tiptoeing about.

It is almost alway about taking big gutsy steps, putting ourselves out there with ideas and plans that seem crazy to everyone, risking our finances – sometimes even relationships, hearing a lot of naysaying, and generally going against the odds.

Which is why I had to do it, and why you must do it too. When next tempted to go with your instinct for settling for less, think hard about what you want to do and where you want to be, and go for more, even if the result is a gut-wrenching experience of beginning at an age when we are supposed to be experts.


My next missive will be about that experience, and about the differences in handling – emotionally, intellectually – this turmoil and change in one’s forties.


Meanwhile, it is all about you:


What bold moves have you made in the course of your career change?

What bold move are you going to make this week, so Fortuna knows where to turn her attention?

  2 comments for “Career Change – Ask and You Shall Receive

  1. January 19, 2015 at 6:45 am

    Great, insightful post and kudos to you for being so bold! My bold move is to go to the SF Writer’s Conference next month and learn more about the publishing industry, look for a mentor and network with like minded people :)

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