Mindset And Positioning For Achieving What Matters
The worst mistakes I’ve made in my personal and professional life can all be tied to lies — not lies that I tell to others but ones that I tell myself. They are comfy rationalizations I wrap around my psyche to insulate myself from or forestall uncomfortable truths.
Mostly, those lies have to do with time.
I’ve been fortunate to pursue and achieve cool things. Grow great businesses. Impact customers in lasting ways. To change and save lives. I’ve willed myself and my organization to victory when the odds were stacked against us.
I’ve used improbable victories to sell myself on impossible timelines, selling myself lies and bringing others along for the resultant difficulties.
The lies that we tell ourselves are like an invasive species. They seem harmless or even beneficial at first, but over time, they consume the landscape of honest self-assessment. Choking out insight. Disrupting what was sustainable growth.
Until we recognize the problem, eradicate the newcomer, and return to core truths. Over my career and my life, I’ve been led away from these truths. Suffered. Then, come back to them to thrive.
Two of these truths concern goals. The pursuit and achievement of things of lasting importance.
These truths are twofold:
- It takes longer than you expect
- It costs more than you anticipate (often because of truth #1)
Ignoring these truths has caused me the most mental anguish, while honoring them has brought me the greatest triumphs. Allow me to explain what I mean, why it matters, and how you can harness these truths to shape your life positively.
What I mean by “takes longer”
We tend to be optimistic about how quickly things will happen, discounting the likelihood that life will disrupt us in pursuit of our objectives. Instead of imagining that things will go according to plan, we count on it. We picture the future unfolding exactly as we imagine.
Then, we often encounter the unimaginable.
Life tends to interrupt our intent. Our desire for predictability is upended by the ironic truth that we should expect unpredictable things to happen. Our picture of the future is a guess.
Guessing is as good as it gets, and that is ok.
When I was a kid, a popular family saying was, “Expect it when you least expect it.”
Life is uncertain, and the unforeseeable does not mean unrecoverable. Although we often don’t, we should expect that unexpected things will happen.
So then we accommodate longer in our planning, right?
No — absolutely not. Don’t you dare. We cannot build truckloads of conservatism into our future plans. This is another part of the paradox of pursuing goals. Building products and businesses. Taking steps to build a better version of ourselves.
To envision, pursue, and grasp a vision for a better life.
When we remove aggression from our lives, we become complacent. Our schedules expand to fill whatever time we give them. If we give ourselves more time than we need, we’ll take it.
Then, even after we’ve given ourselves all that extra time, we’ll encounter unexpected things. As a result, we set a timeline, moving it further into the future to ensure we are not late, only to end up late again anyway.
Then what do we do about timelines? Planning?
The amount of time you need will be longer than you think. Knowing that, go with what you realistically think. Not what you hope could happen in an ideal circumstance, but what you think is most likely. Expect to be frustrated in your pursuit, but do not proactively try to accommodate that frustration.
Because you cannot.
No amount of hand-wringing trying to puzzle through hypotheticals will help you arrive at the unforeseeable. The whole point isn’t to construct the perfect plan because all plans are imperfect. Because at the end of the day, it is never the plan that is the most important thing. It is the planning.
The thought that produces the plan. The exercise in thinking through scenarios. Dependencies. Places where things are expected to be difficult. Preparing aggressively to meet the things that you can foresee.
With your timeline set, even though you think it is realistic, act like your timeline is aggressive as hell. Pursue it with a sense of urgency. Like you are under the proverbial gun.
While doing so, ensure you have the financial flexibility to accommodate the unexpected. Overcoming the unexpected never happens for free.
Everything costs something; challenges cost more
Often (but I’ll concede not always), timing has flexibility. Too often, when the timing has flexibility, we do not. Our difficulty stems from the fact that we have made ourselves dependent on that timing. WE NEED it to happen at a specific time.
Because delays have implications for resources, things that take longer than expected require more resources to be completed. Expenses accumulate over time; the old adage that time is money is always true.
We often run into cost problems due to timing. We set the timing based on our available resources. Not our customers’ needs. Or our partners’. But instead, when WE NEED something because of our available resources. Then we stuff our plans into the times we need it.
Not matching our resources to our plan, but instead stuffing too large of a plan into too limited of resources.
Then we are the ones with a sense of urgency because we have made ourselves dependent on the timing. Then, in a turn of events that should be expected, we are not on time, and we have a real problem. Because now the timing has a cost — a cost that shows up in a number of different ways.
Personally
Our reputation is besmirched. We’ve lost credibility. We said we would do it, or it would happen, and it doesn’t. We guaranteed it would succeed, but now it is struggling. Who we are, our integrity and character, feel under assault. Those impacted by the delay feel like we should have known better. Perhaps we know we should have, and that is what makes some of those circumstances hurt the most.
Not because of the criticism but because of the truth within it.
We ignored our subconscious warning that it was unlikely. Because we needed it to work, we told ourselves we’d will it to another improbable victory anyway. Stacking up a series of improbables until the future we’ve imagined became impossible. Guaranteed future disappointment lurking around the corner.
Professionally
The business is impacted. Our careers may be impacted. Relationships damaged. Trust eroded.
The truth is that, often, we come to a place professionally where we do not feel as though we have a choice. We are backed into a corner, unable to contend with the truth because the truth would be very uncomfortable. The conflicts are bigger than we can manage. Being forced to choose between a dim hope it all works out and a conflict we don’t know how to take on does not feel like a choice. We take dim hope over certain and immediate difficulty.
The easy choice and the wrong choice are, so often, the same.
Why we do it
I’ve found myself in situations like this one because I didn’t want to disappoint anyone. I am a people-pleaser. I would hustle to ensure everyone around me was happy and secure, getting stuck between two sets of incompatible desires and trying to make them work.
I’m unsettled when people or organizations I care deeply about are not happy. I feel torn apart, trying to hold the tension between two incompatible desires.
Typically, deep down, I see it coming. That coldness in the bit of my stomach. My body signaling that this goes poorly. I’ve heard that signal, brushed it aside, and campaigned onward anyway. Because deep down, winning at that moment was more important than signing up for expectations I thought I would meet. I rationalized that I’d find a way to make it work, even when I wasn’t confident I could.
I did this at times because the business needed the win. At times, because I did. I came to the same destination by different routes. Finding the same bad things there each time.
You might think I was doing it over again because I’m optimistic. Because I’d made the improbable work before. Feeling like the distance between improbable and impossible was much shorter than it truly is.
The truth is less flattering.
It has less to do with a positive personality trait, although I am optimistic, and more with a negative one. The less flattering appraisal of the situation was that I was cowardly. I lacked the courage to speak to the uncomfortable realities I could see coming around the corner. I preferred to hide those likely realities, hoping something much less likely happened instead — something more positive.
I hoped a distant miracle would relieve me of the discomfort of tackling a painful and immediate truth. Unfortunately, the longer this continued, the higher the cost rose. That time was money, so to speak, both financially and psychologically. That putting myself in such a situation didn’t make me a better man, a better dad, or a better leader.
But, over time, the experience made me more honest with myself.
What to do differently
Confronting our self-deceptions isn’t about diminishing our dreams but making them sustainable. It’s about trading the temporary comfort of lies for the enduring strength of truth. The most courageous act isn’t an impossible victory but having the wisdom to see clearly, plan intelligently, and move forward with ambition and humility.
For me, as far as what this means and what I need to do differently, it is about mindfulness. It is about paying close enough attention to myself that I can recognize those moments when my gut is trying to tell me something. It is about having the patience and discipline to explore those feelings, to listen to myself.
Then, I need to have the courage to reflect what I find there outward.
Allowing myself to live from the inside out instead of from the outside in. Knowing that doing so sometimes produces a hard conversation. Something that makes me uncomfortable. But knowing that if that conversation is inevitable, then it might as well be immediate. Because the discomfort will only grow, as will the cost.
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If you liked this article, check out my article on Work-Life Balance