Only 1 in 3 Americans feel confident about their retirement savings. In the roofing industry? That number is likely even worse.

I've had too many conversations with roofing contractors and sales reps in their late 50s who thought they could just stop working and coast into retirement.

They'd built successful careers, closed thousands of deals, maybe even sold their business—but when we actually ran the numbers, their savings couldn't cover even five years of expenses, let alone 20-30 years of comfortable living.

That's a brutal conversation to have. An even tougher position to be in.

Here's the harsh reality: Your body will eventually force you out of this industry. The only question is whether you'll be financially ready when that happens, or whether you'll be scrambling to find desk work at 65 because you can't afford to stop.

I don't want that to be your story. My mission is helping roofing professionals plan ahead so you can actually enjoy the retirement you've earned—not just survive it.

If you're not sure where to start, this guide walks you through five essential steps to take control of your financial future. From setting realistic goals to building a bulletproof savings strategy, let's ensure your golden years are as comfortable as you've always imagined.

 

Step 1: Understand Your Retirement Goals (What Does "Done" Actually Look Like?)

Before figuring out the "how," you need to figure out the "what" and "why." Most roofing professionals never actually define what retirement means to them—they just assume they'll figure it out when they get there.

That's a mistake.

Visualize Your Ideal Retirement Lifestyle

Take a moment right now and actually picture it:

Are you living minimally, comfortably, or lavishly? Maybe you want to downsize to a small lake house and fish every morning. Or perhaps you want to maintain your current standard of living—nice truck, comfortable home, regular travel. Maybe you're dreaming bigger—winters in Florida, summers in Colorado, that bass boat you've always wanted.

What does a typical week look like? Are you completely done with roofing, or do you see yourself consulting on commercial projects part-time? Spending time with grandkids? Traveling in an RV across the country? Volunteering? Playing golf four days a week?

Where are you living? Same house you're in now (hopefully paid off)? Moving somewhere with lower cost of living? Relocating closer to kids or grandkids? The location decision dramatically impacts your retirement income needs.

Get crystal clear on exactly what you want. Vague goals produce vague results.

Estimate Your Annual Income Needs

Now let's get practical. What does that lifestyle actually cost?

Start with your current situation: Are you living within your means right now, or are you stretching to make ends meet? If you're earning $90K but spending $95K, we've got work to do before worrying about retirement.

Example scenario: You currently earn $100K annually but only need $75K to maintain your desired lifestyle. Why the difference? Because by retirement you plan to:

• Have your mortgage paid off (eliminates $24K/year)
• Own your vehicles outright (no more $600/month payments)
• Be debt-free (no credit card or loan payments)
• Have reduced work-related expenses (no commuting, work clothes, tools)

Suddenly that $100K lifestyle becomes affordable on $60-70K in retirement.

Factor in healthcare costs: This is the wildcard. Healthcare gets exponentially more expensive as you age. Even with Medicare (which starts at 65), you'll have supplemental insurance premiums, copays, prescriptions, and potential long-term care costs.

Plan for $15,000-25,000 annually in healthcare expenses in retirement—more if you have chronic conditions or retire before Medicare eligibility.

Consider cost of living changes: Maybe you're relocating from California to Tennessee (massive savings). Or maybe you're moving from rural areas to be near grandkids in an expensive city (massive increase). These location decisions can swing your income needs by 30-50%.

For roofing business owners: Don't forget to separate personal lifestyle needs from business expenses. Many owners have inflated personal spending because business and personal finances blur together. Get clear on what YOU actually need versus what the business provides.

The goal isn't creating a perfect projection—it's creating a realistic target to build toward.

 

Step 2: Calculate Your Retirement Savings Needs (Running the Real Numbers)

Back when I was a financial advisor, we used sophisticated software for retirement projections. Here's the truth: you don't need any of that. Free online calculators work perfectly fine if you're willing to spend 15 minutes being honest with yourself.

Let's work through an example relevant to roofing professionals:

Meet Carlos: The Roofing Sales Rep Planning Ahead

Carlos is 40 years old. He's been in roofing sales for 12 years, currently earning $85,000 annually. He lives within his means and is comfortable maintaining his lifestyle on $65,000 in retirement (about 75% of current income).

He plans to retire at 67, wants to be completely debt-free by then, and is willing to contribute 12% of his income toward retirement.

His calculator inputs:

• Current age: 40
• Retirement age: 67
• Current income: $85,000
• Desired retirement income: $65,000 (75% replacement)
• Current retirement savings: $75,000
• Annual contribution: $10,200 (12% of income)
• Expected rate of return: 7% (conservative for stock-heavy portfolio)
• Expected inflation: 3%

The results: Carlos needs approximately $2.1 million by age 67 to safely generate $65,000 annually. With his current plan, he'll accumulate about $1.4 million—falling short by $700,000.

That shortfall means Carlos either needs to work longer, save more aggressively, reduce retirement expenses, or adjust his expectations.

Understanding the 4% Rule (Your Retirement Income Lifeline)

The 4% rule is simple: You can safely withdraw 4% of your total portfolio value annually without running out of money over a 30-year retirement.

Examples:

• $1 million saved = $40,000/year safe withdrawal
• $1.5 million saved = $60,000/year safe withdrawal
• $2 million saved = $80,000/year safe withdrawal
• $2.5 million saved = $100,000/year safe withdrawal

Want to be more conservative? Use 3% instead. This provides extra buffer for market downturns and longer retirements.

For roofing business owners: If you're planning to sell your business, that sale price factors into your retirement number. A $500K business sale invested at 7% generates roughly $35,000 annually using a 4% withdrawal rate—significant income to supplement other retirement savings.

Additional Considerations That Change Everything

Social Security income: Don't ignore this. If you've worked consistently, Social Security might provide $20-35K annually. That significantly reduces how much portfolio income you need. However, don't count on Social Security being your primary income—use it as supplemental support.

Pension income: Rare in roofing, but some union positions offer pensions. If you have one, factor it in.

Rental property income: Many roofing professionals invest in rental properties throughout their careers. If you own three rentals generating $12,000 annually each, that's $36,000 in passive income before touching your investment portfolio.

Higher investment returns: The example used 7% returns. Historically, the S&P 500 averages closer to 10% long-term. Adjusting to 8-9% dramatically improves projections—but be conservative. Better to exceed expectations than fall short.

Inflation: The Silent Retirement Killer

A dollar today doesn't buy what it did 20 years ago. It won't buy what it does now in another 20 years.

This is precisely why we invest—to maintain purchasing power over decades. Factor 3-4% annual inflation into your planning. That comfortable $70,000/year lifestyle today might require $120,000+ in 20 years to maintain the same standard of living.

Try the calculator yourself: Use a free retirement calculator (available on Fidelity, Vanguard, or NerdWallet) and run your personal numbers. Play with different scenarios—retiring earlier, saving more, adjusting expenses. See what it takes to hit your target.

Knowledge is power. Running the numbers might be uncomfortable, but it's infinitely better than discovering the shortfall at 65.

 

Step 3: Build a Strong Savings Plan (Automation and Consistency Win)

It's no secret: the earlier you start investing, the greater your probability of successfully reaching retirement goals. Every year you delay makes the journey exponentially harder.

The best time to plant a tree was 30 years ago. The second best time is now.

Maximize Tax-Advantaged Retirement Accounts

These accounts are your secret weapons. They provide massive tax benefits that supercharge your results.

401(k) Plans: The Employer-Based Powerhouse

A 401(k) is offered through your employer. Many roofing companies—especially larger ones—offer these plans.

How it works:

• You contribute a percentage of each paycheck directly into the account
• Money is invested in a menu of options (typically mutual funds and index funds)
• Contributions happen automatically before you ever see the money (out of sight, out of mind)
• You gradually adjust to living on the remainder

The employer match: This is FREE MONEY. Many employers match 50-100% of contributions up to a certain percentage (commonly 3-6% of salary). If your employer matches 50% up to 6%, and you contribute 6% ($5,100 on $85K salary), they add another $2,550. That's an instant 50% return before any market gains.

Never leave employer match money on the table. It's the easiest, highest-return investment you'll ever make.

2024 contribution limits: You can contribute up to $23,000 annually ($30,500 if you're 50+). Most roofing professionals should aim for at least 10-15% of income—more if you're starting late.

Tax benefits: Traditional 401(k) contributions are pre-tax (reducing current taxable income). Roth 401(k) contributions are after-tax but grow tax-free. Many plans offer both options.

IRA (Individual Retirement Account): Your Personal Investment Vehicle

An IRA is an account you open independently through brokerages like Fidelity, Vanguard, or Schwab. You control everything—investment choices, contribution timing, management.

Key differences from 401(k):

• YOU choose the investments (unlimited options, not a set menu)
• YOU must set up automatic contributions from your bank
• YOU must actually invest the money—it doesn't happen automatically

Critical warning: Don't let cash sit uninvested in your IRA. I've seen people contribute for an entire year, check their account, and discover the money just sitting in cash earning 0.5% because they never actually bought investments. Set up automatic investments when you fund the account.

2024 contribution limits: $7,000 annually ($8,000 if you're 50+). Not as much as 401(k)s, but still valuable.

Traditional vs Roth IRA:

• Traditional: Pre-tax contributions, pay taxes on withdrawals in retirement
• Roth: After-tax contributions, completely tax-free withdrawals in retirement

For most roofing professionals earning $60-120K, Roth IRAs make excellent sense. Pay taxes now while you're in moderate tax brackets, enjoy tax-free income in retirement.

For Roofing Business Owners: SEP IRA and Solo 401(k)

If you're self-employed or a business owner, you have access to much more powerful retirement accounts:

SEP IRA: Allows contributions up to 25% of net self-employment income, maximum $69,000 (2024). Simple to set up and maintain.

Solo 401(k): Allows contributions up to $69,000 as employer + employee ($76,500 if 50+). More complex but offers maximum contribution flexibility.

These accounts let high-earning contractors put away $50-70K annually tax-deferred—building retirement wealth rapidly while reducing current tax liability.

The Savings Hierarchy: What to Fund First

Priority order for roofing professionals:

1. Emergency fund ($1,000 starter fund immediately)
2. Employer 401(k) up to company match (free money)
3. High-interest debt payoff (credit cards above 15% interest)
4. Emergency fund increase (3-6 months expenses)
5. Max out Roth IRA ($7,000/year)
6. Max out 401(k) ($23,000/year)
7. Taxable brokerage account for additional investing
8. Real estate investments, business investments, etc.

Emergency Fund Milestones (Non-Negotiable for Roofing Pros)

Roofing income can be volatile—storm seasons boom, winters slow down, economic downturns kill new construction. You MUST have cash reserves.

Emergency fund milestones:

• $1,000: First milestone. Covers minor emergencies (truck repair, urgent home issue)
• 1 month expenses: Provides breathing room for unexpected costs
• 3 months expenses: Minimum acceptable emergency fund
• 6 months expenses: Ideal for most roofing professionals
• 12 months expenses: Ultimate security for business owners or commission-only reps

For business owners: You need BOTH personal emergency funds AND business operating reserves. Aim for 3-6 months of operating expenses in business accounts to handle cash flow gaps.

Automate Everything (Remove Willpower from the Equation)

The biggest savings mistake isn't poor investment choices—it's inconsistency. Most people get paid, spend freely, then save whatever's left (usually nothing).

Flip the script: Pay yourself first through automation.

Set up automatic transfers:

• Paycheck hits → 15% automatically transfers to 401(k)
• Paycheck hits → $500 automatically transfers to Roth IRA
• Monthly → $300 automatically transfers to emergency fund

Remove decision-making from the process. You can't spend what you never see.

Over time, you adjust to living on the remainder. That adjustment happens faster than you'd expect, and the wealth accumulation happens automatically in the background.

 

Step 4: Diversify Your Investments (Don't Put All Your Eggs in One Ladder Rack)

Some people view investing as risky, comparing it to gambling. Usually, that's because they don't understand it or never took time to learn what a proper investment plan looks like.

Here's the truth: NOT investing is the real risk. Leaving money in checking accounts earning nothing while inflation eats away 3-4% annually guaranteed is far riskier than investing in diversified portfolios.

Asset Allocation: The Foundation of Investment Strategy

Asset allocation means dividing your portfolio across different investment types. This is more important than individual investment selection.

The main asset classes:

Stocks (Equities): Ownership in companies. Highest growth potential, highest volatility. Historically average 10% annual returns long-term. Essential for building wealth.

Bonds (Fixed Income): Loans to companies or governments. Lower returns (4-6%), lower risk. Provide stability and income. Important as you near retirement.

Cash/Cash Equivalents: Savings accounts, money markets, short-term CDs. Lowest returns (3-5% currently), no volatility. Provides liquidity and stability.

Real Estate: Property investments. Can provide income (rentals) and appreciation. Many roofing pros prefer this since they understand property/construction.

Index Funds: Baskets of stocks tracking market indices (S&P 500, Total Market). Offer instant diversification. My preferred investment vehicle.

Sample Asset Allocations by Age

Age 25-40 (Growth Focus):

• 80-90% stocks
• 10-15% bonds
• 5-10% cash

Age 40-55 (Balanced Growth):

• 70-80% stocks
• 20-25% bonds
• 5-10% cash

Age 55-65 (Pre-Retirement):

• 50-60% stocks
• 35-40% bonds
• 5-10% cash

Age 65+ (Retirement):

• 30-40% stocks (inflation protection)
• 50-60% bonds (income and stability)
• 10-20% cash (living expenses)

General rule of thumb: Subtract your age from 110 to get your stock allocation percentage. At age 45, you'd hold roughly 65% stocks (110 - 45 = 65).

Adjust Strategy Based on Retirement Timeline

20+ years from retirement: Be aggressive. You have time to recover from market downturns. Focus on growth through stock-heavy portfolios. Short-term volatility doesn't matter—long-term growth does.

10-20 years from retirement: Balanced approach. Still growth-focused but beginning to add stability through bonds. You're accumulating serious wealth now—protect some of it.

5-10 years from retirement: Shift toward preservation. Gradually increase bonds and reduce stocks. You can't afford a major market crash right before retirement—protect what you've built.

In retirement: Balance income needs with inflation protection. You still need stocks to maintain purchasing power over 20-30 years, but bonds provide stable income and reduce portfolio volatility.

Keep It Simple: Index Funds for Busy Roofing Professionals

You're busy running jobs, managing crews, closing deals. You don't have time to research individual stocks or constantly monitor investments.

Solution: Low-cost index funds.

My recommended simple portfolio:

• 60% Total US Stock Market Index Fund
• 20% International Stock Market Index Fund
• 15% Total Bond Market Index Fund
• 5% Cash/Money Market

Adjust percentages based on age and risk tolerance, but this covers you across US companies, international companies, and bonds—instant diversification with minimal effort.

Set it and forget it. Rebalance once or twice annually. Otherwise, let compound growth do the work.

 

Step 5: Prepare for Non-Financial Aspects of Retirement (Because Money Isn't Everything)

2020 taught us something important: when people were confined to homes for extended periods, their experiences varied dramatically based on financial security, relationships, and how they chose to spend time.

That's exactly what retirement looks like—extended time without the structure of work. The difference between a fulfilling retirement and a miserable one often has nothing to do with money.

Plan How You'll Spend Your Time

If you didn't have to work tomorrow, how would you fill your days?

For roofing professionals specifically:

Many guys who've spent 30-40 years in this industry struggle when they stop. Their identity was wrapped up in being "the roofer" or "the contractor." When that ends, they feel lost.

Healthy retirement activities for ex-roofers:

• Stay connected to the industry: Consulting, training younger reps, teaching at trade schools
• Pursue long-delayed hobbies: Fishing, woodworking, golf, hunting, travel
• Volunteer work: Habitat for Humanity (using your skills), coaching youth sports, community projects
• Part-time work: Home inspections, property management, handyman services (staying active without the grind)
• Travel: Finally take that RV trip across national parks, visit family regularly, explore new places

Start building these interests NOW. Don't wait until retirement to discover hobbies. Join groups, develop relationships, invest in activities outside of work. Those interests and connections become your retirement foundation.

Your Health Is Your True Wealth

What good is accumulating $2 million if you're too unhealthy to enjoy it? Watching savings get drained by medical bills and medications isn't anyone's retirement dream.

The roofing industry reality: This work destroys bodies. Knees, backs, shoulders, hands—repetitive strain adds up. Many roofing professionals reach retirement age physically broken down.

Invest in health maintenance now:

• Regular exercise (especially strength training to protect joints)
• Preventive healthcare (annual checkups, addressing issues early)
• Proper nutrition (not just gas station food between jobs)
• Adequate rest (easier said than done during storm seasons)
• Address chronic pain/injuries before they become debilitating

The goal: Reach retirement healthy enough to actually DO the things you've been planning. Travel requires mobility. Golf requires functional shoulders. Playing with grandkids requires energy.

Don't sacrifice your health building wealth, then spend that wealth trying to buy back health. It doesn't work that way.

Build and Maintain Your Social Network

Retirement can be isolating. You lose daily interaction with crews, customers, and industry peers. If work relationships were your primary social outlet, retirement leaves a void.

Start building non-work relationships now:

• Join hobby groups (fishing clubs, golf leagues, car clubs)
• Stay connected with old friends
• Develop couple friendships (if married) that aren't work-related
• Volunteer in community organizations
• Participate in church, civic, or recreational groups

Let these relationships grow over decades. They become your retirement social foundation—the people you fish with Thursdays, play poker with Fridays, travel with occasionally.

For married roofing professionals: Discuss retirement expectations with your spouse. Many guys retire and drive their wives crazy being home all the time. Have honest conversations about space, activities, and expectations. Retirement can strengthen marriages or destroy them—communication determines which.

The Identity Transition

For many roofing professionals, their work IS their identity. "I'm a roofer" isn't just a job description—it's who they are.

Retirement requires transitioning that identity. You're not a roofer anymore—so who are you?

Start thinking about this transition years before retiring:

• What do you value beyond work?
• What legacy do you want to leave?
• What brings you fulfillment outside of roofing?
• Who are you when you're not on a roof or closing deals?

These aren't easy questions, but answering them makes retirement smoother and more fulfilling.

 

Taking Action: Your Retirement Roadmap Starting Today

Retirement planning is one of the most important financial steps you'll take. There will come a time when you stop working—by choice or by physical necessity. Being prepared well in advance makes it a smooth transition where you live your golden years with confidence and peace of mind.

Your Next Steps Depend on Where You Are Now

If you're in your 20s-30s: You have time on your side—the most valuable asset in investing. Start immediately, even with small amounts. $300/month from age 25-65 at 9% growth becomes $1.4 million. Don't waste these years.

Action items:

1. Start emergency fund ($1,000 immediately)
2. Contribute to employer 401(k) up to match
3. Open and max out Roth IRA
4. Increase contributions 1-2% annually

If you're in your 40s-50s: You're entering peak earning years. This is when you should be saving most aggressively. You've likely figured out your career, have experience, and can earn top dollar.

Action items:

1. Max out all retirement accounts (401(k), IRA, SEP/Solo 401(k))
2. Build 6-12 month emergency fund
3. Pay off high-interest debt
4. Consider real estate investments
5. Run retirement calculations annually to stay on track

If you're in your 50s-60s: You're in the final accumulation phase. Every dollar saved now matters enormously. You're also transitioning from growth to preservation.

Action items:

1. Maximize catch-up contributions (50+ allows extra $7,500 to 401(k), $1,000 to IRA)
2. Shift asset allocation toward bonds and stability
3. Pay off all debt before retirement
4. Calculate exact retirement date based on savings progress
5. Develop post-retirement identity and activities

If you're behind on savings: Don't panic. Don't give up. Adjust expectations and get aggressive.

Options:

• Work longer (every extra year dramatically improves retirement security)
• Save more aggressively (50-70% of income if possible)
• Reduce retirement expenses (downsize house, relocate to lower cost area)
• Plan for part-time work in retirement
• Consider Coast FIRE (save enough for growth to fund traditional retirement)

 

The Roofing Professional Advantage

You have skills most people don't. You understand property, construction, and maintenance. Leverage these advantages:

Real estate investing: Your industry knowledge makes you better at identifying good properties, estimating repair costs, and managing renovations. Many roofing pros build retirement wealth through rental properties.

Business sale: If you own a roofing business, that's a retirement asset. Start building it to sell 5-10 years before retirement. A well-systematized business can sell for 2-4x annual profit—significant retirement capital.

Consulting income: Your expertise has value beyond physical labor. Semi-retirement consulting—training programs, manufacturer rep work, project oversight—keeps you engaged with income but without the physical demands.

 

The Bottom Line: Start Now, Stay Consistent, Adjust as Needed

Retirement planning isn't complicated—it just requires honesty, consistency, and time. Define your goals, calculate the numbers, save aggressively, invest wisely, and prepare for the non-financial aspects.

The absolute worst thing you can do is nothing. The second worst thing is waiting until "next year" or "when things slow down" or "after this next big project."

Start today. Open that IRA. Increase your 401(k) contribution. Run the retirement calculator. Have the conversation with your spouse. Take one concrete action before the day ends.

Your 65-year-old self—relaxing without financial stress, enjoying hobbies, spending time with family—will thank you for starting now.

The ladder is getting taller and your knees are getting older. Make sure your retirement savings are growing faster than both.