The Obvious Choice: 15 Lessons On Success, Profit, And Finding Your Way

The Obvious Choice by Jonathan Goodman

Jonathan Goodman’s The Obvious Choice is a sharp, story-rich, and experience-backed book that reframes how success is achieved in today’s noisy digital economy. Aimed at entrepreneurs, leaders, and self-starters, the book is built around 15 powerful insights that prioritize clarity, simplicity, and human connection over digital theatrics and hypergrowth illusions.

With a mix of autobiographical narrative, practical frameworks, and candid case studies, Goodman argues that success in business isn’t about chasing every trend or building a viral presence online—it’s about becoming the obvious choice to the right people through trust, specificity, and consistency. This makes it highly relevant to your audience of startup found e rs and self-improvement seekers who often struggle with where to place their limited focus and resources.

Why It Matters for Leaders, Entrepreneurs, and Self-Starters

In the entrepreneurial world, especially in early stages, people are often taught to prioritize visibility over value, volume over precision, and performance over alignment. The Obvious Choice challenges that culture with compelling stories and actionable strategies that teach leaders to:

Build durable, values-aligned businesses rather than viral sensations.
Focus on being “famous to the family” (your ideal audience) instead of chasing mass attention.
Leverage trust-based marketing over traditional funnel thinking.
Systematically de-risk decision-making through self-awareness and strategy.

In one compelling case, Goodman shares the story of “Benjamin,” an aspiring entrepreneur who pivoted from aimless social media posting to applying Goodman’s Human Optimized Marketing System. He made his first sale the same day he shifted his approach.

Summary of Key Ideas and Concepts

Main Premise

Success is not about being louder—it’s about being clearer. The businesses that win are those that build trust, understand their ideal customer intimately, and apply timeless principles with modern tools.

Core Arguments

Trust > Credentials: People don’t buy based on your qualifications; they buy because they trust you.
Small Can Be Profitable: A focused, high-margin business built on relationships outperforms a high-volume, low-margin business chasing scale.
Simplify to Win: Remove chaotic ambition and shiny-object distractions to amplify what already works.
Technology is Fuel, Not Fire: Use digital tools to enhance—not replace—human-centric business principles.
Marketing is Local and Specific: Your best customers live right under your nose—market deep, not wide.

Practical Lessons for Leaders and Entrepreneurs

Start with Subtraction, Not Addition
Before adding complexity, remove what doesn’t serve your vision. This reduces burnout and reveals what truly matters.
Build Trust Before You Sell
Relationships sell more than ads. Focus on trust-building through familiarity, community, and relevance.
Know Your Game and Play It
Are you building a scalable tech startup or a high-trust local service? Don’t confuse business models with influencer aspirations.
Study Yourself Like a Bug
Goodman introduces the “Bug Book” technique—a self-journaling method to identify your most productive, fulfilling patterns.
Become “Famous to the Family”
Market to the few who matter, repeatedly and deeply, instead of trying to impress the many who don’t.
Use the Marble Method
Find your ideal customers by reverse-engineering your happiest and most valuable existing ones.
Marketing is Not Always Online
Great marketing can be as simple as parking a branded van on the right street. Direct, human interactions often outperform algorithmic outreach.
Make Success Predictable
Avoid lottery-ticket thinking. Instead of hoping for a miracle, stack small, consistent wins.
Align Ambition with Reality
True ambition is strategic and sustainable. Chaotic ambition leads to burnout and bad bets.
Limit Your Business to What You Can Enjoy
More profit with less effort and fewer people is not just possible—it’s the optimal path for most.

Part 1: A Few Not-So-Obvious Truths

Jonathan Goodman’s The Obvious Choice begins by stripping away myths that often misguide ambitious entrepreneurs and leaders. In Part 1, titled “A Few Not-So-Obvious Truths,” Goodman lays the foundational mindset shifts that drive sustainable success. Instead of promoting performance hacks or growth-at-all-costs strategies, he focuses on internal clarity, self-trust, and deliberate simplicity.

Chapter 1: When Ambition Results in Recklessness

Broken Clocks

Goodman explains that unchecked ambition can turn into reckless behavior. While society glamorizes ambition, he highlights how ambition, when fueled by constant comparison and digital distractions, leads to chaotic action rather than meaningful progress. The availability of content and constant exposure to others’ wins tricks us into believing we’re behind, which raises our expectations faster than our results can keep up.

The Bug Called “You”

The solution begins with introspection. Goodman introduces the “Bug Book”—a journaling tool to objectively observe yourself like a scientist. Set five alarms a day and record your emotional state from -2 to +2, along with objective notes about your activities. After a week, identify patterns and summarize observations in the third person. This creates self-awareness without emotional bias and helps leaders recognize what energizes or drains them.

Removing Recklessness

Chaotic ambition thrives on anxiety. It seduces us into constant action without questioning impact. Goodman distinguishes between chaotic and true ambition. While the former is reactive and rushed, true ambition is proactive and strategic. Leaders must subtract chaos before adding complexity. By knowing yourself, you remove distractions and become more deliberate in what you pursue.

Chapter 2: Trust in You > Your Credentials

The Synagogue’s Board

In business, people don’t buy based on credentials—they buy based on trust. Goodman illustrates this with a personal story about his financial advisor, Ted, who was referred through his synagogue community. Despite knowing nothing about Ted’s credentials, Goodman and his family chose him based on trust and familiarity. This invisible but powerful trust network creates opportunities that marketing can’t track.

It Hertz

Buying decisions often come down to a single specific need. Goodman recalls buying a TV and trusting a salesperson’s advice solely based on one question about his viewing preference. This specificity built trust and justified the purchase without needing to understand the technical details. Customers don’t need all the facts—they need one meaningful reason to feel confident in their choice.

Your World ≠ Their World

Experts often overestimate how much their audience knows or cares about their credentials. Goodman introduces the concept of “satisficing”—people choose options that are good enough, not necessarily the best. Most customers can’t evaluate the full value of your offering. The key is to make your value obvious and easy to understand, not to overwhelm them with your expertise.

The Dude

Goodman tells the story of a meat deliveryman who drove sales simply by knocking on doors and creating an “everywhere illusion” in a neighborhood. Through repetition, proximity, and human connection, he built trust faster than any digital campaign could. Trust, built through familiarity, can make a small operation feel omnipresent and credible.

Finding Perfect Customers with the Marble Method

To identify ideal clients, Goodman introduces the Marble Method:

Create two lists: your top ten most valuable customers and your top ten most liked customers.
Find the names that appear on both lists.
Study those clients—where they live, what they do, what media they consume.
Use these patterns to find more clients like them.

This method reveals who you serve best and how to find more of them by leveraging real data over guesses.

Beating Michael Jordan

To win in business, you don’t need to compete head-on with giants. Goodman compares it to beating Michael Jordan—you don’t do it by playing basketball. Instead, play a different game. Bolton Foods didn’t try to beat Costco on price or scale; they played their own game with personalized local service. The same applies to entrepreneurs—lean into your unique strengths and avoid direct comparison.

Chapter 3: Success Shouldn’t Be a Surprise

Terrible Story, Great Life

Goodman warns against idolizing outlier success stories. These narratives are crafted for dramatic effect and often emphasize struggle for storytelling purposes. In reality, many successful people live quietly predictable lives without hardship or viral moments. Their success doesn’t make headlines, but it’s far more replicable and sustainable.

Neon Monsters

Even the most successful companies, like Monster Beverage, experienced frequent setbacks. Despite being a top-performing stock, Monster appeared to be underperforming 95% of the time. Goodman’s point is clear: long-term success rarely looks impressive in the moment. Patience and resilience matter more than momentary wins.

Cheating (Well) at Blackjack

Goodman references Edward Thorp, who succeeded at blackjack by betting conservatively even when odds were in his favor. The lesson? Don’t risk your entire business on one good idea. Stack the odds slowly and conservatively over time. Consistency beats recklessness, and staying in the game matters more than a big win.

Connecting the Dots Backward

Goodman reinforces that hindsight creates false clarity. We connect dots only after success happens, falsely believing that the path was predictable. Instead of trying to reverse-engineer outlier stories, focus on steady execution and habits that build long-term leverage.

Chapter 4: Fix What’s Inside Your Fence First

Blinded to the Truth

Entrepreneurs often chase new leads while ignoring existing relationships. Goodman recounts his wife’s experience fundraising for a charity. Social media posts generated no sales, but personal messages to ten friends led to eight purchases. Relationships, not algorithms, drive action. Don’t ignore the low-hanging fruit in your immediate world.

Janet’s Bridge Posse

Goodman shares another example of his aunt Janet, who used her bridge club—a group of retirees—as her referral network for a coaching business. The key insight is that your best opportunities are often hidden in plain sight among the people you already know.

Breezy

Social media can make you believe you’re making progress when you’re not. Goodman discusses “Human Avoidance Marketing” (HAM)—posting online to avoid real conversations. He challenges entrepreneurs to ask themselves daily, “How many people did I talk to today?” Real business happens offline far more often than online.

When Faking It Doesn’t Result in Making It

Pretending to be bigger than you are, or overproducing your image, doesn’t build trust. Authenticity and personal interactions remain the most effective methods for early traction. Goodman emphasizes that being small and human is a strength, not a liability.

Advice from a Billionaire

Goodman quotes an anonymous billionaire who advises: “Don’t build a moat around your business. Build a bridge.” Helping others access you, understand you, and trust you creates more opportunity than hiding behind fancy branding or funnels.

$200 Is $200 Is $200

To close, Goodman illustrates how businesses often overlook small opportunities because they don’t appear scalable. But $200 from a single sale, repeated consistently and sustainably, can build a business more effectively than chasing $20,000 deals that never come. The goal isn’t growth at all costs—it’s clarity, consistency, and compounding trust.

Part 2: Becoming the Obvious Choice

In Part 2 of The Obvious Choice, Jonathan Goodman moves from mindset to methodology. After clearing the chaos in Part 1, he now shows how to actively position yourself as “the obvious choice” to your ideal customers. This section is tactical yet deeply human-centered, reinforcing the idea that authentic marketing rooted in clarity and connection is the most sustainable path to profit.

Chapter 9: Let Your Geek Flag Fly

Goodman encourages readers to embrace their individuality and specific expertise—what he calls “letting your geek flag fly.” Rather than dulling your edges to appeal to everyone, focus on what makes you uniquely passionate and different. People trust those who show conviction and depth, not generalists who try to please everyone.

He explains that deep knowledge and enthusiasm create an aura of confidence and credibility. The moment you become unapologetically yourself is when you begin to attract the right people. Weird, specific, and committed beats broad, bland, and polite.

Chapter 10: Discover the Easy Answer

Rather than always seeking hard work and hustle, Goodman urges you to find the easy answer—the thing you’re naturally good at, that others value and will pay for. Most successful people, he says, don’t win because they try harder. They win because they find a simpler game to play.

To discover the easy answer, ask yourself:

What do people repeatedly come to me for?
What do I do that feels easy to me but is valuable to others?
What types of problems do I enjoy solving?

Your business should align with your strengths, not fight against them.

Chapter 11: Become Famous to the Family

Here Goodman introduces one of the most central strategies in the book: the Human Optimized Marketing System. Instead of trying to win over the internet, focus on becoming “famous to the family”—the small, specific group of people who truly matter.

The Five-Step Human Optimized Marketing System

Build a clear message: Describe what you do in a way that resonates immediately with the people who need it.
Focus on relationships, not reach: Deepen trust through real conversations, not content metrics.
Create structured follow-up: Don’t let interest fade. Stay in touch until people are ready.
Stay visible within a small group: Become omnipresent to your niche.
Give people a reason to talk about you: Create referable experiences.

By using this method, Benjamin, a small-time entrepreneur, made his first sale immediately after pivoting away from vague content strategies and into direct, meaningful outreach.

Chapter 12: #MonkeyFirst

Goodman uses the metaphor of training a monkey to juggle before launching it into space. The lesson is clear: do the hard, necessary thing first. Most people delay critical tasks while working on easier, peripheral activities.

If your business depends on sales calls, the “monkey” is your ability to close. If you need referrals, the “monkey” is asking for them. Prioritize what will truly move the needle rather than polishing logos or fiddling with your website.

Identify the hard, critical thing.
Do that first—even if it’s uncomfortable.
Build everything else around it.

Success comes not from doing more, but from doing what matters most.

Chapter 13: Find Your “So That”

This chapter is about clarifying the real purpose behind what you do. Most business messaging focuses on features and processes, but customers care about outcomes.

Goodman encourages entrepreneurs to identify their “so that”:

I help people lose weight so that they feel confident enough to date again.
I build websites for small businesses so that they can finally look as good online as they are in person.

The key is to dig deeper until you uncover what truly matters to your client. This emotional resonance is what drives purchasing decisions.

While social media has its place, Goodman argues it’s a dangerously inefficient way to build a business if you’re relying on it for short-term sales. He compares it to a savings account, not a checking account—valuable over time, but unreliable in the now.

The Four-Stage Content Creation Framework

Observe: Pay attention to what your ideal audience reacts to and struggles with.
Document: Collect raw thoughts, feedback, or stories that highlight real-world experiences.
Distill: Turn observations into short, focused messages or ideas.
Distribute: Share your content where your audience is already paying attention, but don’t expect instant returns.

Goodman emphasizes that content is more about developing credibility and future opportunities than immediate leads. If you’re creating content, do it for long-term trust, not instant conversion.

Chapter 15: Whales and Minnows

This final chapter in Part 2 breaks down the difference between small clients (“minnows”) and large, ideal clients (“whales”). While many chase volume and end up with a school of minnows, a few whales can deliver 10x the value with less work.

The key is to:

Define who your whales are—people who value what you do and are willing to pay well.
Design your offering around their needs.
Say no to minnows who don’t fit, freeing up time and energy for the right clients.

Goodman’s advice is clear: make space for the big opportunities by aligning your business around the clients who matter most.

A Story: Elaine’s Second Act – Becoming the Obvious Choice

Elaine Simmons had just turned 60. After four decades in corporate leadership roles—most recently as the COO of a Fortune 500 logistics firm—she was preparing to retire. But Elaine wasn’t ready to slow down. Years of mentoring younger leaders, optimizing complex operations, and building high-performing teams had gifted her with a wealth of insight.

She wanted to launch her own leadership and strategy consultancy—offering executive coaching, change management consulting, and organizational turnaround strategies. But despite her track record, Elaine faced doubts:

How would she stand out in a noisy, younger-skewed consulting market?
Should she start posting on LinkedIn every day?
Did she need to build a personal brand?
Would people care about her if she didn’t have a slick online presence?

That’s when she picked up The Obvious Choice by Jonathan Goodman—and everything changed.

Elaine realized she didn’t need to become an online entertainer or a content machine. She simply had to be famous to the family—the people who already trusted her, respected her, and needed her help. She didn’t need a bigger audience; she needed a sharper message, deeper relationships, and the courage to lead with who she was.

Step 1: Study Herself Like a Bug

Elaine created her Bug Book to track her energy and focus over a week. She set 5 daily reminders and recorded how she felt (-2 to +2), what she was doing, and with whom.

She discovered:

+2 when mentoring rising female executives
-1 during tech troubleshooting and content creation
+1 when presenting in small, focused rooms
-2 when trying to write blog posts to “stay relevant”

Action Item: Hire a tech VA to handle digital assets and content publishing. Only commit to writing when it feels purposeful—not forced.

Step 2: Define Her “So That”

Elaine didn’t want to be a generic consultant. She refined her core message:

“I help mid-career female leaders build the confidence and operational clarity to lead big transformations—so that they rise into C-suite roles without burning out or compromising who they are.”

This gave emotional weight to her offering and helped clients see what they become as a result.

Action Item: Include her “so that” statement in her website intro, pitch deck, and conversations.

Step 3: Use the Marble Method

Elaine created two lists:

Most Valuable Clients (from her internal mentoring work): Directors and VPs she’d coached who went on to executive roles.
Most Liked Clients: The mentees who stayed in touch, credited her with their growth, and felt energized after conversations.

Three names overlapped.

Action Item: Interview those three women to understand what they valued, where they hang out (networks, conferences, groups), and what they’re struggling with now.

Step 4: Park the Van on the Right Street

Elaine resisted the urge to market to everyone. Instead, she focused on:

3 corporate women’s networks
2 leadership associations she was part of
A private Slack group for female execs

Instead of running ads or creating a funnel, she:

Reached out to 10 warm contacts in her network with a personal note
Offered 3 pilot coaching spots at a discounted rate for testimonials
Attended two offline events and asked questions instead of pitching

Action Item: Create a referral loop. Every time a new client engages, she sends a handwritten thank-you and a note asking: “Do you know someone who needs this too?”

Step 5: Become Famous to the Family

Elaine developed a simple Human Optimized Marketing System:

Clarify Message: “I help female VPs lead big transformations so they get promoted to the C-suite—without burning out.”
Deepen Relationships: Monthly check-ins with her top 10 contacts.
Visibility Strategy: One guest podcast or in-person panel per quarter.
Referral Fuel: Provide tools and scripts clients can use to refer her.
Social Media = Savings Account: She posts once a week—only when she has something real to say.

Action Item: Schedule one visibility-building action and one connection-nurturing activity each week. Keep it human, not high-volume.

Step 6: Let Her Geek Flag Fly

Elaine stopped trying to sound like a millennial coach on Instagram. Instead, she leaned into her decades of operational leadership, her love of systems, and her dry humor. She brought real executive war stories into her client conversations—and found that people loved it.

Action Item: Record a short video series called “Boardroom Lessons” where she breaks down real-life transformations in 5-minute clips for her private network.

Step 7: Avoid Chaotic Ambition

Elaine kept her business simple:

5 high-ticket executive clients per quarter
One 8-week group coaching experience per year
No more than 3 visibility projects at a time

She knew she didn’t need a million followers—she just needed the right dozen people saying her name in the right rooms.

Action Item: Set quarterly revenue goals tied to lifestyle, not scale. Track metrics that matter: referrals, rebookings, and client outcomes—not likes or reach.

Elaine’s Consulting Launch Strategy in Summary

Internal Clarity: Use the Bug Book to track flow and design her business around her energy zones.
Customer Fit: Apply the Marble Method to find and replicate her best clients.
Simple Systems: Use Human Optimized Marketing to build trust and visibility with zero complexity.
Authentic Positioning: Let her executive strength and personal style shine without mimicry.
Deliberate Growth: Stay profitable by focusing on whales, not minnows. Scale trust, not noise.

Final Note

Elaine didn’t launch with a funnel. She didn’t build a content engine. She didn’t dance on LinkedIn.

Instead, she launched her consultancy with a few direct messages, three trial clients, and a crystal-clear offer.

Within six months, she was fully booked, working 20 hours a week, and making more than she did in her last year as COO.

And the best part?

She didn’t feel like she had to be someone else to make it work.

She was simply the obvious choice to the people who mattered.

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