When the Prototyping Mindset Fails Us
A reflection on learning and failing from an overthinker
Have you ever been ghosted by a date? What about by a recruiter for a dream role you’ve been negotiating for?
Has a client questioned your methods and scope of work, after agreeing to them? Has there been an incident outside your control that completely flipped the transformation plan you made? Has a potential client ever negotiated your budget even before agreeing on what the scope would be?
Do you take these personally?
The answer to this question can go and has gone both ways for me. One the one hand, when I was starting out as a strategy consultant, I often couldn’t separate my worth and self-esteem from the day-to-day operations of the work and so I took every question and negotiation as an attack. On the other hand, now years into the work, I can usually muster enough effort to remove myself emotionally from the situation and just focus on the contents in front me.
With every situation though, I always thought about what I could do differently to achieve a different outcome. In hindsight, any mistakes that I saw can easily be rewired as lessons learned (like how everything is feedback). I learnt a lot.
And so when I decided to close down the consulting company that I started, it didn’t feel like a big deal. For most of its lifetime, the company was a small operation. The work was some version of me and a facilitator running workshops, facilitating in internal stakeholder meetings, going into the (literal) field to empathize — all in the name of helping clients deliver better products and experiences. I’m saying all this partly to reflect, and partly to give myself credit for all the work that I put in before feeling extremely burned out.
When I stopped recruiting and finding leads, stopped sharing my works, it was a natural decision. I would’ve gone crazy. I was so overwhelmed. At the time, I didn’t see it as a failure, but a series of lessons learnt on how (not) to do projects and who to work with. I was happy with the decision…
… until I’m not. It’s been almost a year since, and I realized that I should’ve framed it as a failure, and faced directly the fact that I, indeed, have made many mistakes.
Fast forward to now, when I’m struggling with not landing a dream role and having projects come to a stand still. These and other general life disappointments helped me realize that I over-rationalize everything as a learning.
The company that I decided to shut down, for instance, a prime example of this. I focused on the miscommunications with the vendors, the lack of delegation and authority I asserted, the bespke solutions that allowed the projects to veer off path (but delivered the objective). I certainly think that reframing into the more negative mistake prone mindset might have done me some good. The mistakes I made were: that I chose the wrong vendors to begin with, that I didn’t stick to the plan, that I took personally the variables outside of my control.
I developed functional habits like doing summaries after calls, following up with open leads with kind words, spotting early signs of resistance in people which helped me take action and prevent future problems. But I didn’t get to really feel how painful disagreements and my own missteps can be; the regret in wasting time and decisions, the hurt that comes from trusting the wrong people.
I didn’t feel so much as turn any experience into a checklist of improvements, a mental ladder to climb for next time, a badge of honor that, yes, I too have seen so-and-so situation and can laugh with empathy at networking events.
I recently stumbled on a clip of Toni Morrison talking about self-forgiveness, how we have to “go through the fire” and “experience the full fall… and complete self-loathing” of one’s terrible doing. While nothing I have done would qualify as quite as catastrophic as to deserve shame or hatred, there is a lesson here to be sure that feeling — not thinking — is a critical step in the learning too.
As someone who overthinks everything and who sometimes prefer neat categories of things to put my mind to, I am hoping to strike a balance between holding a prototyping mindset while also feeling the disappointment of making mistakes. It’s a juggling act that I will probably have to do for the rest of my life, but at least I realize now that it is ok to both label things as a prototype and feel the full force of the failure. It’s weirdly comforting.
