The Messy Middle

Success doesn't come from blazing beginnings or dramatic conclusions. It's forged in the messy middle when persistence meets adaptation.

1. The Middle is a Rollercoaster of Highs and Lows

Starting a new venture often feels exhilarating, but the real work begins after the initial excitement fades. The messy middle is an emotional and unpredictable phase that tests resolve. This period is rife with uncertainty, alternating between inspiring highs and crushing lows.

Scott Belsky experienced this firsthand while building Behance, a platform for creative professionals. In the early years, his idea struggled to gain traction. Critics doubted it, and even internal morale wavered. Yet, Belsky pressed on, riding out the challenges while seeking growth. The secret wasn’t avoiding the volatility but learning to navigate through it.

Success here means bracing for the emotional swings and striving to keep the lows from sinking too deep while extending the highs. Over time, this creates a more sustainable upward trajectory.

Examples

• Belsky’s journey involved chronic self-doubt and the use of anti-nausea pills due to stress.
• Each small victory, such as new user growth, kept his team focused during lows.
• Entrepreneurs often find themselves lifting others’ spirits even when their own resolve weakens.

2. Short-Term Rewards Keep Long-Term Momentum Alive

Humans are wired to thrive on immediate gratification, yet ventures require long stretches of persistence with little external recognition. To sustain morale, create moments of celebration with self-styled milestones.

Behance’s small victories became points of pride. For example, when Google finally recognized “behance” as a legitimate search term instead of auto-correcting it to “enhance,” the team toasted to this mini triumph with cheap Champagne. These custom-made milestones gave Belsky’s team an ongoing sense of achievement.

Setting these manufactured markers aligns with human psychology, helping teams endure the long, often thankless grind until larger goals can be realized.

Examples

• Celebrating a feature’s minor improvement energized the Behance team.
• Writers often announce word-count milestones among peers for motivation.
• An artist sharing early sketches celebrates small progress before larger commissions unfold.

3. Stay Self-Aware During Peaks and Valleys

Triumph and failure don’t just affect ventures; they influence us personally. During peaks, ego can cloud judgment, making us dismissive of advice. During valleys, insecurities may lead us to unfairly shift blame to others.

Remaining self-aware during these extremes allows leaders to make objective decisions. Belsky observes that successful founders are those who welcome and even seek constructive feedback, while egotism or defensiveness derails less adaptable leaders.

Fight these tendencies by embracing humility. Recognize when you’re overconfident and when stress clouds your vision. Openness to external viewpoints sharpens your strategy in any situation.

Examples

• Belsky noticed founders who actively pursued feedback often had better outcomes.
• Executives who ignored early warnings about product flaws faced disastrous launches.
• Self-aware leaders find collaborative fixes in tough discussions rather than retreating.

4. The Long Game is Worth Playing

Short-term goals tend to dominate day-to-day thinking, but ventures thrive when future possibilities come into focus. Building relationships and exploring ideas that might not pay off immediately can lead to extraordinary results down the line.

Bill Gurley, a tech investor, embodies this mindset by dedicating years to building trust in industries and ideas without rushing transactions. This long-term perspective helps cultivate opportunities that others might overlook out of impatience.

Neglecting this foresight, as Blockbuster did when rejecting Netflix’s offer in 2000, comes with steep costs. Designing for future viability is worth the slower pace.

Examples

• Netflix’s $50 million acquisition offer by Blockbuster is now a legendary missed opportunity.
• Gurley’s years of exploratory talks in new sectors helped him identify Uber early.
• A fledgling artist might receive mentorship years before landing major clients.

5. Build Better, Not Just Fix Broken

It’s easy to focus on weaknesses, but amplifying what already works separates successful ventures from stagnant ones. Optimization should be a key strategy during high points to accelerate progress.

Google popularized A/B testing, tweaking one variable at a time to refine user experiences, like testing button colors for improved click rates. This approach pushes projects beyond baseline functionality into true excellence.

Apply this philosophy not just to products but to your daily habits or team dynamics. Small, consistent improvements make a big impact over time.

Examples

• A tech start-up finds greater user retention simply by fine-tuning their sign-up process.
• Athletes enhance performance by focusing on nutrition and sleep optimization.
• Teams experimenting with shorter meetings find noticeable productivity increases.

6. Celebrate Wins Without Losing Boldness

Reaching the “finish line” of a venture often marks the start of complacency. The daring mindset of early days, when big risks and bold experiments felt necessary, ironically fades with success.

Facebook combats this by reminding employees they are only “1 percent finished.” This philosophy pushes the company to constantly rethink and evolve, maintaining the flexibility and drive from its earliest days.

Sustaining this mindset post-success ensures ongoing innovation and keeps ventures alive and thriving in the long haul.

Examples

• Facebook’s evolution from social media into a broader utility platform reflects ongoing boldness.
• Companies investing in R&D after market success maintain future relevance.
• Successful artists who continue experimenting avoid being boxed into old patterns.

7. Manufactured Motivation Drives Tough Times

Motivation doesn’t appear magically during struggles. You must actively cultivate it by reminding yourself of your why, connecting team members to each other, and focusing on what progress has been made.

Daily team meetings where Belsky reviewed triumphs and current experiments provided needed morale boosters. In tough moments, momentum is easier to regain when individuals believe effort translates into meaningful progress.

Embracing proactive motivation tools keeps ventures moving forward, inch by inch.

Examples

• Project managers using “work-in-progress” displays to show team progress lift morale.
• Writers relying on accountability partners for encouragement stay productive longer.
• Teams rally around shared setbacks by collectively finding solutions.

8. Shift Your Perspective on Setbacks

Failure, as painful as it feels, is a valuable kind of feedback. Belsky points to setbacks as opportunities for recalibration. Instead of blaming failures, dissect them for learning opportunities.

Turn missteps into chances for growth by asking what could be improved systematically for next time. This reframing bolsters endurance in periods that feel unbearable.

This lesson, though simple, ensures people emerge stronger from every dip.

Examples

• Companies reviewing why a product failed often create superior follow-ups.
• Athletes analyze losses to refine skills for future competitions.
• Writers revisiting rejected drafts often develop clearer final work paths.

9. Finishing is Not Endgame

True success doesn’t mean closing. Thinking of ventures as infinite ensures room for innovation. Facebook, again, embodies this unending mindset by continuously redefining what it does.

Dormancy comes when leaders stop asking, “What’s next?” Avoid treating your work as complete and embrace curiosity, regardless of initial success.

This mindset keeps both organizations and individuals from stagnation.

Examples

• Amazon’s expansion beyond books into multi-faceted e-commerce and tech domains reflects evolution.
• Entrepreneurs who pivot ideas post-launch often sustain longer impact.
• Celebrated teams asking tough questions often sustain relevance across industries.

Takeaways

1. Regularly set and celebrate small, achievable goals to maintain momentum during difficult stretches.
2. Seek out and remain receptive to constructive feedback, especially when ego or doubt clouds judgment.
3. Treat every success as a starting line, keeping curiosity and adaptability alive to ensure continued growth.