Having Difficult Conversations…With Yourself

Last Tuesday I attended a professional development class titled “Having Difficult Conversations,” and the topic revolved around courage and using it to face your fear of having a difficult conversation with your peer/coworker, subordinate, or supervisor/employer.

Considering the week (and month) I had leading up to that class, I felt as though I was already using my courage to not only live out more of my dreams but also handle difficult conversations with confidence.  At the moment, my talks were with staff of a former employer who, for whatever reason – by purpose or mistake, failed to issue my separation pay.  Thinking of the worst case scenario and the alternatives within and outside of reach is pretty tough to bear and will either make or break whatever amount of courage you have on hand or can muster up in the first place.  Of course, the stress of not knowing when – or IF – you will receive money you were promised and thereby counting on to make your month’s bills calls for that special kind of courage that supersedes hesitation to confront the issue head on.

So as I sat in the class listening to the situations participants were encountering where the skill to tactfully hold these three types of difficult conversations with others was needed, I thought to myself how we are all in the same boat together.  We’re each just weathering a different aspect of the same “uncertainty” storm – uncertainty of how an employee will react to the feedback or news you’ve given, of whether a peer or friend will work with you to resolve the issue at hand, or the uncertainty of what your next course of action will be if an employer doesn’t hear your suggestions or choose to support your requests.

But today, as I reflect on the result of one difficult conversation had (with that employer finally issuing me my separation pay) and the latest difficult conversation awaiting resolution (with the employment office making a decision on my claim for benefits based on the details provided and disputed), I wonder about the other type of conversation not mentioned during class – the difficult conversations you have with yourself.

From the moment I was offered employment at a place that would later put me in this precarious financial existence, I’ve had one difficult conversation after another with myself – first about the pros and cons of accepting the job being offered, then about the shock of experiencing the actual work environment I’d placed myself in and what could be done to make the best of a “not looking too good” situation.  Then, of course, there was the very, very difficult conversation I repeatedly had with myself about the foolish decision I’d made to ignore ALL the red flags surrounding said employer and instead proceed to purchase my ticket to board their sinking ship anyway.  Until, finally, there was the inner conversation about the options I now had left on the table to somehow get off the disastrous ride I’d been taken on and find my way to the safety of shore.

Many of these conversations with myself were harsh, demeaning, and (more often than not) very tearful – exactly the outcomes we were instructed in class on how to prevent.  Worst of all, unlike the conversations covered in class that had a clear resolution, this type of difficult conversation doesn’t end with a polite parting of ways.  Why?  Because you are always with the other party, and so talk can resume, replay, and even escalate at any time your mind takes you there.

So, how do you go about handling the difficult conversations you have with yourself?  Having these types of conversations with anyone – whether a peer, subordinate, or supervisor – is a challenge in finding courage to overcome your fears of the unknown.  Having difficult conversations with yourself is a lesson in forgiveness of mistakes made and courage to forge ahead facing whatever known consequences you’re left with as a result.  Both are not isolated or one-off events.  Instead, all difficult conversations are constant tests that become more complex and layered over time, experience, and age.  I guess, with both, the trick is to not run from the challenge but accept it AND to always keep moving forward regardless.

What I do know is this – had I known then what I know now about the organization and the job they were offering, I would have declined it thereby avoiding the situation altogether.  The funny thing is I DID know, or at least that small soft voice within me knew and begged to be heard.  And had I listened to intuition and followed my gut instincts, I would not be in the very situation I find myself in now.  But, we can’t change the decisions of the past.  And that’s why continuing to have difficult conversations with yourself is necessary, especially when done in kindness and from a place of love and not personal blame.  Because that’s how we can take our experiences as lessons learned to grow more mindful of the signs, omens, or “flags” that appear to prevent those poor choices from being repeated in the future.

This was the second time I made this type of career mistake.  Here’s to hoping the third time will be the charm if ever presented with a similar employment “opportunity.”   For sure, I will have a long difficult conversation with myself but this time listening to my instincts to make the choice I believe is best for me based on the signs given.


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