I think I’ve noted before that, by nature, I’m generally an optimist, always looking for the way forward, especially during crisis. We’re all products of our experiences, our upbringing, signature events in our lives, etc., that shape our attitudes, our beliefs and our commitments. I’m no different in that respect. I take the same optimistic approach not only with events, but with people, as well…….to a point. Whether personally or professionally, we’ve all had that one person that we interact with day after day, week after week, month after month; even year after year in some cases. We care about them, we worry for them, but every time we walk away after the interaction, we think to ourselves, Why won’t they change? Maybe it’s a family member, or someone we work with, or someone we’ve been trying to help for a long time. Maybe they’re just negative by nature. Maybe they don’t believe in themselves. Maybe they have a victim mindset that couldn’t possible entertain the thought Maybe it’s me! Yet, every time we see them, we try to encourage, instill confidence, compliment, or tell them how much potential they have. We offer unsolicited tips, recommendations; even a book or two that might influence their mindset, while all the time silently saying to ourselves Why won’t they change? Maybe we even feel it’s hopeless, but we keep clinging to the hope that they’ll somehow change. That there’s some special piece of information that we can give them that would change everything. Maybe we keep buying them books they’ll never read. Maybe we keep sending them to counseling or seminar sessions we know they don’t want to go to and that we know they won’t listen to. Maybe we keep leaving voicemails or emails that we hope will somehow get through, yet never do; all the while thinking Why won’t they change? So, when is enough enough? I believed for a long time that every person under my leadership (both personally and professionally), was worth saving regardless. I’ve even invested (to an unhealthy degree at times) in self-examination and reflection to ensure I was adapting as much as I could without sacrificing my core values; while also ensuring I was providing as much opportunity as I could for that person to be as successful as possible. What I’ve learned, especially over the last few years, is that not only is that naive and unrealistic, it’s much more costly to me as leader, and to others under my influence to keep saying Why won’t they change? There’s a very fine line between grace and accountability. That line of demarcation (if you will) is called enablement. As leader, if you spend too much time enabling, you do so at your peril and the peril of everyone else in the environment. So, when is enough enough? Enough is enough when drama and dysfunction are the only things continually coming out of a black hole that you keep pouring everything positive into. Truth Be Told, that’s when it’s time to ‘free their future up’ and yours, as well.