5 Lessons From Failure I’m Relying on in 2025

For the past 11 years, I’ve been an entrepreneur, relying entirely on businesses that I founded for my livelihood. This self-reliance has brought many wonderful moments of success—but for every one of those highs, I’ve encountered ten disastrous lows. Such “mandatory learning” moments of financial peril and near-death business experiences have, in retrospect, taught me invaluable lessons.

With 2025 upon us, I’m reflecting on five specific lessons I’ll prioritize this year. By sharing them, I hope to keep myself accountable and help others who face similar challenges.

Lesson 1: Trust, but Hone, My Intuition

Early in my career, it felt natural to trust my gut—before repeated failures taught me that’s not always enough. More recently, I’ve overlooked my intuition by taking larger leaps of faith on decisions that didn’t resonate with me, especially concerning hiring, partnerships, and objectives. Sometimes they worked, but often they led to bigger failures.

Going forward, I’ll only commit to leaps of faith I can treat as experiments, so I’m always learning and validating. That means honoring my intuition while also applying a logical framework to ensure the decision “feels right.”

Lesson 2: Use Advice, Correctly

Advice is powerful, but following it blindly can sink a business. While most people who share their opinions mean well, every situation is unique. What works in one context may be disastrous in another.

1. How it’s delivered: Good advice shared in the wrong way—or with a hostile tone—loses its value and can sow distrust or demotivation.
2. The wrong advice: People recognize patterns and offer suggestions based on incomplete information. One person’s “proof of product–market fit” might just be a lucky streak.

I remind myself to process advice as if I’m reading a book: determine the assumptions behind it, see if it aligns with my own situation, and check whether it reinforces my intuition.

Lesson 3: Focus Relentlessly, Numerically

Relentless focus, backed by measurable outcomes, has yielded my best career results. However, I’ve learned the hard way that setting vague goals—or stopping at qualitative priorities—leads to confusion and subpar performance.

Despite natural resistance to metrics (some view them as limiting or time-consuming), I’ve found that meaningful, trackable goals are the bedrock of alignment and success. Going forward, any priority I set will have an accompanying, measurable KPI or target, even if it’s a rough metric. The data orientation is transformative and ensures accountability.

Lesson 4: Master the Numbers That Actually Matter

There are infinite ways to measure success, but each business has a handful of metrics that matter most day to day. While SaaS metrics like CAC and LTV help investors gauge performance, those may be less relevant if the biggest challenge is making payroll next month.

I’ve realized I need a hands-on understanding of my company’s finances—from cash flow to daily operational metrics. By tracking and internalizing the numbers that directly influence my decisions, I avoid distractions from overly complex forecasting or investor-driven metrics. My daily, weekly, and monthly check-ins help me operate effectively in real time.

Lesson 5: Trust the Right People—for Only the Right Things

It’s invaluable to have mentors, peers, and colleagues whose advice I can lean on. However, expecting every confidant to offer great guidance on every topic is unrealistic. The “halo effect” can fool me into believing that someone who’s helped me in one area can do the same in all others.

Moving forward, I’ll be deliberate about matching the right person to the right challenge—always evaluating their area of expertise. And, of course, I’ll refer back to my intuition (Lesson 1) and my framework for processing advice (Lesson 2).

Conclusion

My list of lessons learned could fill a dozen articles, but these five points anchor my 2025 planning. By trusting and refining my intuition, filtering advice, focusing quantitatively, tracking the right numbers, and carefully selecting who I trust (and for what), I’m aiming to avoid the costly errors of the past. Here’s to fewer “mandatory learning” moments and a more deliberate, grounded 2025.