Career Advice for All the Wayfinders; Time To Be #SorryNotSorry

As a person who spends my time, generically speaking, in the realm of Human Resources, I tend to be a magnet for those around me wondering what to do next – professionally speaking.

The questions (but really anxieties posing as questions) that I hear most frequently are effectively variations on the following:

  • Everyone around me seems to have achieved [INSERT: title/salary / other prestige-implying-noun] but [with sad, shameful eyes] I seem to be still finding my way.
  • At every interview, I totally stumble on the “Where do you see yourself in five years?” question. Between you and me [hushed voices] I have no idea [reenter shameful eyes]
  • I’m so anxious about choosing my next job/opportunity. Which one is “right” and what if I get it “wrong?”

  • Now, if you’re a person who has a clear ambition and a strategy designed to get you there, then truly my most authentic congratulations to you.

    However, if you’re someone with whom any of the above sentiments resonate, please take a deep breath and know that you’re not any less than the ambitious amongst us.

    So sit with me. I have thoughts.

    Thought #1: What the [BLEEP] is wrong with “still finding your way???”

    People whose resumes “make sense,” follow a clear path and tell an intuitive story may have an easier time getting a foot in the door for many jobs. I won’t debate that.

    However. Look around us, at the moment we’re in. #MeToo, talk of diversity in its many forms – race, gender, neurodiversity, etc. I coach those who come to me to simply stop apologizing or letting shame be the story line of their “wayfinding” journey, and instead to let the diversity of their portfolio of experiences be the headline.

    I tell them to find the “pride points” – the things that make them uniquely them. Because we’re shaped by all of our experiences – they’re all valid, they all accumulate.

    Does an MBA weigh more than a year of wanderlust-inspired travel, or a year working as an Uber driver or a barista meeting people from all walks of life?

    That’s up to you and how you frame it.

    Personally, I’ve done warehouse operations management (in steel-toed boots and a hard hat, wielding a whistle), client management, and project management. Oh and that year of maternity leave? #SorryNotSorry.

    The math here has wound up favorably for me. Today I run my own business and I’m damn good at what I do.

    Thought #2: What if NOT having a five-year plan actually makes you more compelling?

    Quick tangent – bear with me. Anyone familiar with Seth Godin? I love and admire him for many things – his capacity to think, invent, connect, and articulate meaning stuns me consistently.

    What I love most about Seth, and what he’s done in every interview I’ve listened to is this. When asked a question, rather than answering it, he seems to assess its value. And frequently, he simply asks – and then answers – a better question. And pretty much always, the answer he provides delivers more value and enlightenment than could any answer to the original question.

    When you’re interviewing for a job, the person asking you this question is working off a script. So help them edit it. Don’t change the subject, but reframe the question.

    Maybe something like… “My five year plan ? How about my five year-aspiration, or vision, or quest?” Choose something meaningful to you – that you also believe will be meaningful to them. It takes you out of a place of needing to apologize for not having a “plan” and instead it puts you in a position of telling a compelling story – of how you seek opportunities or even strive to be “agile” in your career management (bonus points for using a buzzword).

    Don’t apologize for wanting to keep an open mind, do great work but also want to see what opportunities present, what questions call out to you, what skills or talents you haven’t uncovered yet.

    Related: Activation: A Case Study in Innovation

    Thought #3: What if EVERYTHING will end up as the “right” answer… in hindsight?

    Pretty sure it was Shakespeare who said “what’s past is prologue.” Maybe it was someone else. But whomever it was was a genius in my book.

    I tell people all the time – if you look at my resume on paper, you may experience motion sickness or whiplash. At each major decision point, I simply took the opportunity that felt right – that felt sufficiently scary, exciting, engaging – that would push and grow me.

    And that, my friends, is all the “right” move has to be for you.

    If you give me a chance to tell you my story – to show you the thread, and let me pull it through each point on my resume from beginning to end, the narrative will pull you in.

    And that’s by design. I’ve crafted my story – not ahead of time, but in looking back.

    Every experience you have adds to the sum total of who you are.

    And I write this piece with no intention of promoting myself or my business – but simply in the hopes of bringing a moment of comfort, of release, of self-appreciation for anyone who is suffering these anxieties.

    So many of you have come to me. Way many more have not.

    I hope this helps. And I’m here to talk any time.