The Founder’s Paradox: The Shame of Failing at Mindfulness

The thrill of achievement is irresistible. It is gratifying to set a goal, work hard to accomplish it, and then start to look forward to what is next. Thinking beyond today is part of achieving and yet we are often shamed for not being “in the moment.” The paradox between mindfulness and ambition can be disconcerting. This is especially true if you are someone who enjoys constantly striving. You know the best version of you is still coming.

No one should feel shamed for failing at mindfulness — because long-term achievement requires thinking ahead.

Mindfulness has entered our everyday lexicon and exploded in popularity. But what is it really? Merriam-Webster dictionary offers an intriguing definition: “the practice of maintaining a nonjudgmental state of heightened or complete awareness of one’s thoughts, emotions, or experiences on a moment-to-moment basis.” Mindfulness experts promise improved attention spans and increased empathy.

I believe mindfulness is so popular because it is a reaction to our over-subscribed and constantly on-the-go lives. When life gets difficult, it is natural to turn inward to try and find a sense of calm. Many of us are busier than ever, even while staying much closer to home these days. And chaotic and confusing world events only add to the urge to place your awareness on what is right in front of you — instead of pondering about what is ahead.

Is it possible to think strategically about your career and future, without punishing yourself for failing at always being mindful of the present?

The tension is that right now we need to be able to think two steps ahead while also staying on task — everything is changing fast. For me, the way to be both mindful and forward-looking is to know myself, how today’s success leads us forward, and that small accomplishments should be acknowledged.

How will today’s achievements move me forward?

If you are like me, you are already pursuing a plan that supports your larger ambitions. And you have detailed the short- and long-term objectives needed to get there. It is helpful to set benchmarks and milestones. That way, when you are struggling to tie the current to the future, you can quickly visualize the connection between the two and make sure you stay present.

What is my longer-term vision?

You might refer to it as your mission, vision, or true north. No matter what you call it, it is the essence of why each of us wakes up each day and what pushes us to be our best. Purpose encompasses more than just aspirations — it guides everything we do. For me, I know I can stoke this inner fire by keeping it front of mind.

Where can I lift others up?

Purpose and achievement is rarely all about one person. With circumspection, it is plain to see that any great accomplishment is the work of a team. I am grateful for the opportunity at Aha! to create value for our customers and team. Paying attention to today and calling out how others contribute is how I stay grateful. And celebrating perfect moments inspires everyone to keep moving forward together.

Instead of trying to empty your mind, focus on how today is connected to the future and celebrate others who are on the adventure with you.

Progress is propulsive. It builds upon itself and inspires you to keep going. When you know your purpose and your long-term vision, you free yourself to be “in the moment” and work towards the future at the same time. An awareness of the very core of who you are and where you are headed can be a grounding force in the tumult.

If you are deeply ambitious, it is difficult to honor the current and ignore the future. But rather than punishing yourself — connect this moment, honor those experiencing it with you, and look with excitement about the better self you are working to become. That is a lifelong paradox worth grappling with.

About Brian and Aha!

Brian de Haaff seeks business and wilderness adventure. He is the co-founder and CEO of Aha! — the world’s #1 roadmap software and one of the fastest-growing companies in the U.S. He is also the author of the bestseller Lovability. Brian writes and speaks about product and company growth and the adventure of living a meaningful life.

Aha! is the world's #1 roadmap software. We help more than 5,000 companies and 300,000 users create strategic plans. The company was founded in 2013 by Silicon Valley veterans and product management experts Brian de Haaff and Dr. Chris Waters. Aha! is one of the fastest-growing software companies in the U.S. The company is self-funded and profitable, with an entirely remote team. Learn more at www.aha.io.