My practice, Green Retirement, Inc. is celebrating 20 years of being in business this month. I've been in the industry since 1990. And yes, I have fallen on my face more times than I can imagine. I've learned from each failure and have come back stronger. After all, we must be doing something right to still be growing 20 years later?
It is against that backdrop that I eagerly read Sabina Nawaz' Harvard Business Review article, "To build new habits, get comfortable failing". Her thesis, as I understand it, is simple yet counter-intuitive. Durable behavioral change does not come from motivation or discipline — it comes from systematically learning how to fail safely and repeatedly.
She makes the case that most habit formation collapses because individuals psychologically avoid early incompetence. Any meaningful new behavior initially feels awkward, inefficient, or uncomfortable, and people interpret that friction as evidence they should stop. In reality, that discomfort is the mechanism of learning.
Here is what I took as her four practical principles:
First, individuals should “immunize” themselves against failure through small, low-stakes experiments. Instead of attempting dramatic change, repeated minor failures reduce emotional sensitivity to setbacks and build behavioral tolerance. This is something I did not grasp at first in my career as I sought to change the world in my image without any experience or allies!
Second, commitment should occur before hesitation emerges. Public or interpersonal accountability converts intention into action by raising the psychological cost of withdrawal. And hesitation, whether real or perceived, can raise doubts in observers.
Third, failures should be explicitly processed and shared as learning events. Framing efforts as experiments rather than performances shifts mindset from judgment to iteration — accelerating improvement. Ah, so that was the reason the new endeavor in 2002 was called a "pilot project". Hindsight, 24 years later, is 20-20.
Fourth, progress should be measured longitudinally rather than daily. Tracking cumulative effort prevents discouragement and preserves motivation. Stopping while performance remains positive reinforces habit continuation rather than burnout.
Of course, dear reader, you know where my mind went next. Is this applicable to the 401(k) industry, or just life advice?
Naturally, I see her work as highly applicable to retirement plan advisory work — arguably more than to personal self-help.
In the 401(k) ecosystem, failure avoidance is structurally embedded:
• Plan sponsors delay plan redesigns fearing fiduciary scrutiny. • Participants avoid increasing deferrals because short-term lifestyle friction feels like “loss.” • Advisors hesitate to implement innovation (auto-features, managed accounts, fee restructuring) due to client resistance risk.
Behaviorally, retirement outcomes improve through incremental experimentation, not large strategic overhauls. The article maps almost directly onto best-in-class plan governance.
For example, it might be good to sound out auto-escalation, reenrollment, or investment menu simplification with subsets of employees before full rollout. Minor pushback becomes learning, not reputational damage.
Sabina's thoughts on pre-commitment can be seen as Investment Committee Governance discipline. Investment committees that calendar future decisions (IPS reviews, fee benchmarking, QDIA evaluation) act before inertia returns.
Taking public learning and translating it into fiduciary process defense can make sense. Documented “lessons learned” from prior decisions strengthens procedural prudence — the actual legal standard under ERISA.
Her comments on progress tracking dovetail nicely with participant behavior change. Participants succeed when encouraged to improve savings rates gradually (1% escalation) rather than attempting unrealistic contribution jumps.
The deeper implication is this:
The retirement industry often frames fiduciary duty as error avoidance, when superior outcomes come from managed experimentation with documented learning.
That distinction separates transactional advisors from institutional-quality advisors.
So her article is about life — but operationally, it describes how high-functioning advisory practices, investment committees, and participant behavior programs actually succeed.
The Parting Glass
Advisors, Plan Sponsors, and Investment Committees focused on a well-run plan should internalize this mindset organizationally, not personally. The firms that win over the next decade will normalize small, reversible failures in plan design while competitors remain frozen trying to avoid any mistake.