Why Bootstrappers Should Stop Chasing Retirement

A lot of founders plan their business like it’s a launchpad to “never work again.” But the numbers (and the lived experience of people who actually retire) point to a different reality: retiring can be a terrible goal for entrepreneurs—not because money doesn’t matter, but because purpose does.

This idea comes through clearly in Startups For the Rest Of Us Episode 777, where Rob Walling talks with former financial advisor Derek Coburn (author of Let’s Retire Retirement). The conversation is a useful gut-check for bootstrapped founders, especially if you’re building without VC and trying to balance growth with a real life.

And since this post is part of the Small Business Social Media USA series, I’m going to connect the retirement myth to something you deal with every week: how small business marketing (especially social media) should support a sustainable business—not a burnout sprint.

“Retire at 65” is an assumption, not a plan

The fastest way to sabotage a bootstrapped startup is to optimize for a finish line you haven’t questioned.

Coburn’s point is blunt: most people aren’t asked if they want to retire. They’re asked when. That cultural default made more sense when work was physically punishing and life expectancy was shorter.

He cites the historical origin of retirement norms:

• 1889: Germany’s early retirement age choices were tied to shorter lifespans.
• 1935: U.S. Social Security baked in retirement timing when life expectancy was roughly early 70s.

Now, founders often face a different situation:

• Work is increasingly knowledge-based.
• Remote work and freelancing are normal.
• Many entrepreneurs like building things.

If you’re building a company for freedom, it’s worth saying out loud:

The goal isn’t to stop working. The goal is to control your work.

The “two Tonys” math that changes how you save (and how you live)

Coburn gives a simple scenario that should make any founder reconsider extreme saving and extreme grinding.

The scenario

A 45-year-old (Tony) makes $150,000/year and has $150,000 saved for retirement.

• If Tony assumes he must retire at 65, his advisor tells him he needs to save $2,400/month (about 20% of income).
• If Tony plans to work until 70, that drops to about $600/month.
• If Tony plans to work until 75, it drops to about $110/month.

That’s the entire point:

Extending your “meaningful work” timeline can reduce the pressure to hoard money today.

For bootstrapped founders, this matters because the “save everything, defer life” mindset leaks into business decisions:

• Underinvesting in marketing because you’re stockpiling cash
• Avoiding hires forever because “I just need to reach the number”
• Saying no to family time because you’re “almost there”

The reality? If you expect to keep doing something productive later—consulting, advising, building, teaching, freelancing—you can design a financial plan that supports a healthier business now.

Purpose beats leisure (and your body knows it)

One of the most compelling parts of Coburn’s argument is that meaning and comfort don’t produce the same outcome.

He references research distinguishing pursuing happiness (comfort, leisure, self-focus) from pursuing meaning (contribution, connection, building).

The claim: people oriented around meaning show better health markers (like lower inflammation) than those focused purely on personal comfort.

This lines up with a pattern you’ve probably seen:

• Someone retires, loses their daily social structure and identity
• Health declines quickly
• They return to work—not always for money, but to feel useful

Coburn mentions that over 30% of 65-year-olds go back to work—often because they’re bored and disconnected.

For entrepreneurs, the warning is obvious:

If your plan is “sell, retire, relax,” you may be building a life you won’t enjoy living.

The $50,000 moment: a founder’s antidote to burnout

Coburn’s best story isn’t about markets or retirement accounts. It’s about parenting.

He describes a bedtime routine—lying with his kids for a few minutes while they fall asleep. He caught himself rushing it so he could get back to work or entertainment.

Then he reframed it:

If a time machine existed and he could pay to relive one of those nights, he’d write a $50,000 check.

That’s the “$50,000 moment.”

For founders, this is more than a sentimental idea. It’s a decision tool.

Use the $50,000 moment as a weekly filter

Pick one small moment you tend to rush past:

• dinner with your partner
• a workout
• reading to your kid
• coffee with a friend
• an uninterrupted deep-work block

Ask: If I were 70, what would I pay to experience this again exactly as it is today?

Then act like that’s what it’s worth.

A “fun recession” is bad for your marketing, too

Coburn calls it a fun recession: adults aren’t having enough fun, and many can’t even remember the last time they did.

Here’s my opinion: this isn’t just a personal issue. It’s a business and marketing problem.

When you’re depleted, your small business social media efforts start to look like this:

• inconsistent posting (“I’ll get back to it next week”)
• generic content (“Happy Friday!” because you’ve got nothing left)
• zero engagement because you don’t have the energy to reply
• reactive marketing instead of intentional campaigns

Why fun is an unfair advantage in social media marketing

Fun (and rest) creates conditions that make marketing easier:

• Better ideas: you write clearer hooks and stronger stories
• More consistency: you can keep a posting schedule without resenting it
• More personality: your brand stops sounding like a template
• More engagement: replying to comments doesn’t feel like a chore

A sustainable founder builds sustainable marketing.

What “retiring retirement” looks like for bootstrapped founders

If you’re thinking, “Okay, but I don’t want to code 40 hours/week at 70,” good. That’s not the point.

A healthier target is:

Build a business that funds your life now and gives you options later.

Coburn and Walling discuss common paths that keep purpose and flexibility:

• Consulting or freelancing (high control, immediate cash flow)
• Coaching/advising (experience becomes an asset)
• A smaller business you enjoy running (lifestyle-first)
• A portfolio of products (one big bet becomes many smaller ones)
• Mini-retirements or sabbaticals (rest without abandoning meaning)

This aligns perfectly with the non-VC path:

• You don’t need a giant exit to “win.”
• You can compound trust, audience, and distribution over time.
• You can build a company that fits your actual life.

The practical bridge to social media (Small Business Social Media USA)

If you want your startup to last, your social media strategy has to be built for the long game too.

That means:

1. Pick 1–2 platforms you can sustain (don’t cosplay as a media company).
2. Use a realistic posting frequency (2–4x/week beats 7x/week for 3 weeks, then nothing).
3. Turn your work into content:
   • customer questions → posts
   • product decisions → behind-the-scenes threads
   • lessons learned → short founder stories
4. Build community, not just reach: reply, DM, comment, collaborate.

If you design your marketing like you’re racing toward retirement, you’ll burn out. If you design it like you’re building a long, meaningful career, you’ll stay in the game.

A simple action plan for this week

Coburn’s recommendation is to pause and question your assumptions. That’s smart, but founders do better with something concrete.

Here are three practical steps that don’t require a financial advisor meeting next Tuesday:

1. Write down your default retirement assumption.

   • “I’ll retire at 65.”
   • “I need $X to be safe.”
   • “After the exit, I’ll relax.”

2. Replace it with an option-based plan.

   • “At 60, I want the option to work 10–20 hours/week.”
   • “At 55, I want a business that doesn’t rely on me daily.”
   • “I want to keep building, but on my terms.”

3. Align your social media goals with that plan. If your goal is sustainability, your content should support:

   • durable lead generation
   • authority building
   • community
   • a repeatable marketing system

That’s how you market without VC—and without sacrificing your 40s just to reach a made-up finish line.

Where this leaves the “retire early” dream

The retire-early narrative sells a clean story: grind now, live later. Bootstrapped founders know life doesn’t work like that.

You don’t need to romanticize exhaustion to be successful. You also don’t need to fear work. Meaningful work is one of the best assets you can cultivate, especially when you can choose what it is, who it’s for, and how much of it you do.

If you’re building a small business in the U.S. and trying to make social media marketing actually produce leads, here’s the stance I’ll stand behind:

Don’t build a startup to escape work. Build a startup that makes work worth doing.

What would change in your business—and your posting strategy—if you stopped chasing retirement and started designing for freedom, purpose, and staying power?