This is probably going to seem like one of the most big-headed questions you have been asked but I need your advice on finding a truly challenging job role.

I have applied to, and been employed in, far more jobs in my lifetime than can possibly be considered healthy. There is a common theme, if I am not initially overqualified I will always without fail come to terms with the job abnormally quickly. While in essence this seems like an advantage from the outside it is anything but; within a few weeks I will generally have mastered most aspects of the role, (assuming that the job contains no seasonal responsibilities,) in a few more weeks I start picking my duties apart in order to tailor them to my work style and within a few months I have the entire position down to a fine art. Which is where things get sticky, after this point I simply get bored and my motivation goes entirely downhill and I am either forced to take a new position or to exit the company entirely before my lack of focus begins affecting my performance.

This process has never taken longer than 6-7 months -often occurring even sooner- and as there are often no opportunities to move on to a more challenging position within the same company I end up leaving to find something else. While I have amassed several glowing recommendations in this fashion I’ve still never held a job consistently for longer than 8 months, and, it’s a cycle I can’t help but want to break.

Basically, I’m just asking what are the most challenging positions you have come across? (That don’t involve a start up. I’d rather save that rabbit hole for a few years down the line.)

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12 replies
  1. Penelope Trunk
    Penelope Trunk says:

    You mistake your job to be doing a task list. The job, in any job, is to make people like you. That’s how you get more control over your career so that you can have more choices about the work you do. So by the time you get your work under control so you can focus on making people like you, you leave. You are scared to do the real work of adult life which is getting along well with people and helping them in ways you are not paid to help them.

    Stick around and try to learn that, or you will find yourself largely unemployable after a while.

    If you cannot do that, then you need to work for yourself.

    Penelope

    • Brenda Craig
      Brenda Craig says:

      Penelope, you never fail to take my breath away with your laser-point insight: “the real work of adult life, which is getting along well with people and helping them in ways you are not paid to help them.” Which takes us back to homeschooling, and why this simple and amazing insight is NEVER taught in schools. You are awesome. Thanks.

  2. cortney
    cortney says:

    take the time before jumping to the next company to and find out if there is room to grow with them? i think it’s the norm that it takes years for new positions to open up within a company unless it’s a start-up, right?

  3. Janna U
    Janna U says:

    I think Penelope is spot on.

    Another thought – You didn’t say what line of work you’re in, but I wonder if you’d be more excited about a job that involved some kind of “problem solving.” When you solve one challenge, another is waiting for you.

  4. Pirate Jo
    Pirate Jo says:

    How large are the companies you have been working for? It has been my experience that the larger the company is, the smaller the job is. You might be happier in a smaller organization where you are closer to the top and where the scope of your position is wider and more directly related to the day-to-day changes and challenges that face the company. You don’t always see that if you work for a giant-sized corporation, buried beneath layers and layers of management. (Unless you want to manage people, in which case you might want to shoot for one of those management positions yourself.)

    How much ownership of your work have you had in the past? Have you been responsible for the outcomes of your work, or has that responsibility resided with your manager, where nothing is really being delegated to you but the mechanics of the job? If your job is to do the tasks assigned to you by people above you, then your job IS a task list and that’s exactly what’s wrong with it. Maybe you need to be in a position where you have real responsibilities of your own, or where you see more of the whole picture – the entire A to Z process rather than just a single letter, over and over. You may have more luck with smaller companies, if that’s what is really boring you, and not just the absence of a technical challenge.

  5. Lauren
    Lauren says:

    Become a consultant in “business process engineering”. Go to companies and reengineer their workers’ processes for maximum efficiency like you normally do with your own processes. Get paid big bucks, and then move on to the next company.

  6. Becky Castle Miller
    Becky Castle Miller says:

    Become a consultant, like a management consultant or a business intelligence consultant, for a consulting firm. Companies will hire your employer, and therefore you, to come on-site and solve a problem for them. The work is constantly changing – when you fix something for one client after several weeks or several months, you move on to the next client and the next challenge. It involves a lot of traveling, which you probably also enjoy.

    This would give you the benefit of constant new challenges AND would let you stay with one employer for many years, letting you take Penelope’s advice and work on making people like you.

  7. Lori
    Lori says:

    This is interesting. I had a theory that it took about three months to get comfortable in a new position and up to three years to make the job yours. Then I started my current position. I had to keep asking for more work, and creating more duties that would benefit the company – I was lucky I had that freedom. I have been working my current job 2 1/2 years now and I am ready for a change with new challenges, but there is literally nowhere else for me to go within the company. It is a sweet company with fantastic benefits, but I have recently started to read the want ads. But I have also learned that what Penelope says is true, you must make an effort to let people become close to you. I am NOT like that, I prefer to work with my head down and eat my lunch on my own, but after looking around at my office I see that is true.

    While I’m an INFP, I have a co-worker with less schooling and experience than I, and I affectionately call her “The Mayor” (to myself). . I love her – and so does everyone else. And I see that she is getting recognition in the office, despite no special talents except being able to amuse the crowds. She truly is nice as well as a comedian! So I think Penelope is right. Good luck getting to know your office, or if you decide to leave again – in finding your dream job.

  8. channa
    channa says:

    This. Been doing it for five years, it’s the best job if you are purely driven by learning and challenge. But there’s also a huge people skills component and if you aren’t good at that you’ll hate it.

    Alternative would be to join a huge, complex, political and rapidly changing organization at a management level. Then it will take you a year or more just to figure out the organization and where you stand.

    Or get a PhD and spend your life doing research that is unique in the world.

  9. Pete
    Pete says:

    I hate to admit it in this case, but your advice sounds correct.

    I’m not particularly people-oriented, but I’m not anti-social either. I tend to look at my work as a task list too, which is a common approach in technology-oriented roles.

    Many technology folks tend to prefer working with who can display specific skillsets and qualifications (and generate specific tangible results), and so it’s easy for truly social IT employees to be perceived as “brown-nosers”. Personally, I’ve always known that the work was about the people and not the tech to some extent, but the notion that “your job is getting people to like you” still bugs me on some level for some reason.

  10. Lorraine
    Lorraine says:

    Hi Penelope

    What do you mean by “The job in any job is to get people to like you.”

    How would I balance this out on a day to day basis? Could you give an example of what this looks like?

    I’m very literal and visual in my learning style.

  11. Gautam
    Gautam says:

    I tottaly understand. I find it hard to stick to a company for more than 7 to 8 months. Its not because i dont deliver but i just dont find it challenging anymore. it takes me 3 months to get the hang of things and roughly 3 more to get it down packed and tailored to my style after which its all downhill. I have realised I need constant challenges and growth oppurtunities ( not only in terms of financial or promotions but like adding and learning new skills, concepts and behaviours). I love travelling and after a few months I start hankering for going to new workplace or even a new city.
    I need some serious help.

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