The Could-Haves and Should-Haves of Life

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When I sit down to write, I often reflect on what is happening in my own life or what is swirling around the collective. Lately, I’ve been having many conversations with friends and coaching clients who are expressing regret that they didn’t make certain decisions in life when the opportunities to do so presented themselves. These regrets can be relatively small - “I should have taken that great apartment when it became available,” “I wish I had stuck with playing the piano,” “Why did I buy that expensive dress I’ll never wear?” - and don’t impact one's life trajectory too much. But then there are the regrets that have much deeper consequences and leave us with lifelong wounds. I know people who have married for financial security or social status and now regret the gilded cages they find themselves in. I know people who have regretted choosing a career because it pleased their parents and now dread every waking day they go to work. But to me, the saddest of all is regretting a love that drifted out of your life because you were too afraid to tell someone how you felt. Most chances rarely come back around in life, and…

…not all regrets can be undone.

Life is all about decisions, and regret is a by-product of making a choice that does not align with our inner, authentic selves. It is a decision that keeps us from trusting our internal guidance and ultimately awakening and elevating. Regret can keep us stuck in the past, re-enacting “what ifs’ instead of being solidly present in the now. I’ve seen people make decisions to spite others, to perpetuate a lie, to prove a point, to win at all costs, or to resist seeing something from another perspective. I’ve also seen how NOT making decisions has kept people stuck in negative loops or self-sabotaging behaviors because they are too stubborn or scared to make different choices. I have seen people miss precious opportunities because they think and think and overthink until an opportunity passes by. And I’ve seen people give in to procrastination to avoid the stress of making a decision.

Kim Eastburn posing in front of a tree

Decisions are admittedly hard, and it’s not always clear which way to land. I help other people make them every day, yet I sometimes find myself paralyzed with life’s smaller decisions, like which shade of nail polish to choose each week (hence, I always wear the same colors!). But recently, when I had to make some really difficult, seismic, and potentially life-altering decisions, I adapted a strategy that worked so well that I am employing it more and more.

I am not asking for external input; rather, I am looking to the 90-year-old version of Kim for guidance.

Projecting myself into the future (with the me who has more wisdom and lessons leaned under her belt) and asking for direction has made it much easier to assess whether a decision will leave me with regret or not. When I had to make those big decisions and weigh potential outcomes, I meditated and asked 90-year-old me if, looking back on my life, I would have regrets if I did not act. She said (quite loudly and adamantly), “Ab-so-f*cking-lutely! There is one train left in the station, and if you are not on it, there may never be another one!. Do you think you’re going to live forever?”.

I knew that answer did not come from the conditioned ego mind, which would have filled me with self-doubt and kept me fearful of taking a leap into the unknown. That message was as clear as possible, and I knew it came from a place deep inside of me that knew my truth and wanted to speak it. I know I made the right choice because there is absolutely no regret, no looking back, and I have found a peace and happiness that I never knew was possible. I am moving forward without carrying the back-breaking baggage of regret.

Build the Life You Want to Live

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Too many of us are living with regret because we’ve forgotten that we are the architects of our own lives. We simply are not making decisions from a place that elevates us toward the awakened, higher-vibrating beings that we are here to become. We’ve handed over decision-making to parents, peers, and even the ghosts of our past mistakes. We’ve abdicated talking to our inner selves because we yield to outdated or exclusionary societal norms, the pathetic need for conformity, the shaming and exclusionary rules and regulations of religions, and even those as moronic and trite as social media influencers and politicians! We have fooled ourselves (through belief or apathy) into believing that all of these external influences know better than we do what is in our best interest! No wonder we have so much strife, sadness, and regret in our lives and our worlds. Who or what keeps us from the courage needed to access our inner wisdom?

That answer lies squarely on us.

I said earlier that not all regrets can be undone, but some can. As long as we have breath in our bodies, we always have the opportunity to right some of our regrettable wrongs, make different decisions, and connect with our higher selves to steer our lives toward peace and happiness. At the end of our lives, when we have become that older version of ourselves and are asked if we have any regrets, what will our answer be?

I know I am planning to say, “Abso-f*cking-lutely not!”


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The Pause

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Beginner’s Mind…Again