Timing & Embracing Failure Is The One Thing Holding You Back

There's this thing in project management I've heard called, "circuit breaking". The phrase probably brings some engineering-minded folks to think of the Circuit Breaker Pattern. While similar, these things are different entirely. Circuit breaking in project management is knowing when to call it quits on a project, a methodology that surrounds the Shape Up project management style.

You and I were probably raised the same: "Quitting is for Losers". While this is certainly inspirational and likely to see you through difficult scenarios that require completion, it's also entirely wrong. From Steve Jobs to Elon Musk, largely successful people have also largely failed numerous times. Not only did they fail, they often called it quits at the right time.

For products, ideas, or companies that were doomed to fail due to circumstances and events that changed the trajectories of success, they have either pivoted or died. Late-stage startups and even large public companies with initially great ideas have fallen to changes in the economy or technology. The thing that distinguishes a highly successful person and others less successful, I believe, is timing & embracing failure. Timing is the hardest to learn, and I confess I'm still learning.

“Far better it is to dare mighty things, to win glorious triumphs, even though checkered by failure, than to take rank with those poor spirits who neither enjoy much nor suffer much, because they live in the gray twilight that knows neither victory nor defeat.”
Theodore Roosevelt

The types of failure I'm familiar with

During my childhood, my parents were self-employed. I watched them struggle and I watched them flourish, a product of boom/bust. As technology changed, their business changed with it, shifting from vacuum cleaners [yikes] to home security systems. I remember seeing them pivot, struggling with learning curves and new clientele. After some struggle their business absolutely flourished, and I watched them do very well for the family for quite some time. By this time, I had grown quite a bit and was helping them on the weekends and over the summer when they needed an extra hand [- my first taste of sweat equity].

My parents had been buying supplies from a distributor over the life of that side of the business. After many supply issues, quirks in the distributor themselves, and distance from the nearest supplier, they had begun to formulate a startup idea. As they met more and more competition in their market and struggled with supplies, they decided that starting up their own distribution company was the next step to building an empire. I think they were entirely correct, as there was a demand for supply in the area and margins were often lucrative.

But then, the 2008 financial crisis was upon them. I remember it very clearly. Friends of the company who were builders going bankrupt. Projects halted. Customers default on invoices due. Supplies bought for projects orphaned. Things lined up in my parent's minds. This shift in their business demand brought about a perfect time for a new venture, with initial supplies and capital as well. But the market was wrong. The supplying business was thought up for the very business that dwindled. Within a year of opening the business, with a 3,000 sqft showroom and thousands invested, it failed. We worried creditors would come after our home and cars, but thankfully they never did. This was the first time I had been in proximity of a business failure.

Months before the pandemic I had launched a small startup tackling small business growth opportunities by way of mobile ordering. A SaaS that offered custom mobile apps for individual businesses. This was before Doordash swallowed local business. I was able to sell this intellectual property after I deemed it dead, but I made numerous mistakes and missteps in its growth including team choices, bootstrapping over VC, and TTM (Time-To-Market).

After the soft failure of my mobile order startup, I worked for a late-stage startup grocery business that went public and eventually went bankrupt. There were numerous mistakes and missteps that took place: