The Art of Failing Up

Life Lessons

The Art of Failing Up

I’m not good at that. Why would I bury myself in what I’m not good at? That makes me uncomfortable. I’ve not assured a win.

Will I lose who I am? OR, will my worldview be transformed?

The way things are now

During childhood, we create our mental model of what we’re good at versus what we are not. Sometimes, it’s not apparent. For example, a generalist well-rounded in language, mathematics, science, economics, arts, history, and geography may decide to pursue a career in law.

They go the distance and obtain all the degrees and accreditations. They are in a cycle of locking themselves tighter and tighter to their societal role every step of the way. They may continue to touch on other subjects via their hobbies, being well-read, a musician, or tinkering in coding or carpentry.

Most people see everything as okay. Your lane is marked. Stay in your lane. Choice of home, a partner in life, children, and even the car you drive — are all well within the perceived norms.

Woke up, fell out of bed
Dragged a comb across my head
Found my way downstairs and drank a cup
And looking up, I noticed I was late
Found my coat and grabbed my hat
Made the bus in seconds flat
Found my way upstairs and had a smoke
And somebody spoke and I went into a dream

- John Lennon, A Day in the Life

Then one day, they may wake up and realize they’re not in love with their partner, or their children do not take the opportunities they worked so hard to give. The job that used to define them is now work — a means to pay a wealth of bills. Perhaps they are living up to all life expectations without questioning them. Life may have become dull and monotonous.

How do you define success?

Health, wealth, and happiness — We are all destined to get sick, old, and die. Wealth does not provide for happiness, and happiness is not guaranteed by wealth.

So how do we increase all three if the way things are is mediocre?

Setting goals to live within your integrity

The entire act of playing the game of chess is setting yourself up for conflict. Your opponent is pushing their moves against yours, and in the process, you learn about each other and yourself.

• For one, you may be a dominant player who wants to win in the least number of moves.
• You may have memorized all the plays and rely on that knowledge for the upper hand.
• You may play for fun and want to mess with your opponent for an indirect win.

Whatever your flavor, you lean into your playing style and enjoy as the game unfolds. Perhaps you win, perhaps you lose. But ultimately, you shake hands with your opponent, have a good laugh, and walk away to play another day.

In the same way, you can address your position in life. With your partner, you may seek to challenge your relationship. You may push yourself to be uncomfortable to spend more time attending to their love language or needs. Some people do this without thinking, but many — need a crisis or breaking point before they enter into new behavior. They fail at their marriage, and they recognize something of themselves in that realization.

For a career, you may join a software company and inevitably start coding while considering the company’s legal needs. Because you’re centered on your integrity, you are valued as someone who not only voices but sets constraints within the legal boundaries for what the company needs to provide while feeding your curiosity to extend the boundaries of your knowledge.

For home and balance, you wake up one day realizing you’re spending all your time on your phone or working when your kids are dancing around your head, looking for your attention. You have 30 minutes with them before school and a couple of hours after. You decide to very painstakingly put aside the work addiction in favor of spending time with your kids. You recognize that you can work during work hours and you can be with family during family hours.

Mindfulness and reflection

Seeking out challenges in life can still be a safe bet, but the real failing-up occurs when you throw yourself into a career or life with some level of risk and learn how to succeed with integrity intact.

What I have learned through failing up:

• Academia is rife with power plays, jealousy, and rivalry. I was a naive pawn early in my career. Navigating with a goal-oriented purposefulness helped me come out unscathed.
• A Ph.D. is not worth killing rats over. You need to question people for their microaggressions against your integrity and ethics.
• Recognizing the emptiness of titles and accolades.
• Motherhood comes along in its time and not before.
• Miscarriage teaches a mother how precious the life she nurtures is.
• Anyone can become an expert on anything with the right level of effort.
• Startups are crucibles for practicing grit, exponential learning, and agility to adapt.
• You will not be promoted for being a cog in the machine.
• Leaders are human and as buried in the trance of work as you are.
• You are lucky to have a manager who recognizes your value, coaches, and mentors you to grow.
• Practicing empathy is excellent, except when you forget to put your needs first.
• The pattern of burnout is from setting self-criticism too high. Who do you need to impress but yourself?

Growth and transformation

When you can look at a challenge as an opportunity to grow and learn — you essentially turn life into more of a chess game from which you are excited to learn. It's no longer about personal victory but more about the lessons you need to learn along your journey.

Your worldview transforms when you realize you don’t need to own a house to have children, you don’t need a computer engineering degree to be valued in a tech company, and you don’t need to celebrate Valentine’s day to make your partner feel loved.

Your perception, perspective, and choices create your world.