Happy, active diverse group of retirees enjoying life, sailing on a calm ocean at sunset, signifying freedom and financial security

Plan Today for the Retirement You've Always Dreamed Of.

Our Boston-based experts demystify 401(k)s, IRAs, and investments to create a personalized retirement roadmap for you.

Assess My Retirement Readiness

Our Comprehensive Retirement Planning Services

401(k) & 403(b) Analysis

Maximize your employer match and investment choices for optimal growth.

IRA & Roth IRA Strategy

Choose the right account for tax-advantaged growth tailored to your goals.

Rollover Guidance

Seamlessly move old retirement accounts without penalties or headaches.

Retirement Income Planning

Create a strategy for sustainable withdrawals throughout your retirement years.

Social Security Optimization

Determine the best time to claim benefits to maximize your lifetime income.

Long-Term Care Planning

Proactively prepare for future healthcare costs and protect your assets.

Your Retirement Journey, by Decade

20s & 30s

Build the Foundation

Focus on starting early, capturing employer match, and an aggressive growth strategy to kickstart your savings.

40s

Accelerate Your Savings

Increase contributions, diversify your portfolio, and begin catch-up contributions if eligible to boost your growth.

50s

Prepare for Transition

Maximize catch-up contributions, assess your risk tolerance, and meticulously plan for your future retirement income.

60s & Beyond

Live in Retirement

Manage withdrawals strategically, protect your capital, and adjust your plan for long-term longevity.

Common Retirement Questions

This depends entirely on your desired lifestyle and goals. We'll work with you to build a custom projection that accounts for your specific needs, considering Boston's unique cost of living and your income expectations.

Simply put, with a Roth IRA, you pay taxes on contributions now, and withdrawals are tax-free in retirement. With a Traditional IRA, contributions might be tax-deductible now, but withdrawals are taxed later. We'll help you determine which option is best suited for your financial situation and future tax outlook.

Absolutely not. It's never too late to start or reassess your retirement planning. We specialize in creating aggressive catch-up strategies and identifying opportunities to maximize your savings, no matter where you are in your journey. Let's get you back on track.

"I had retirement accounts from three different jobs and no idea what to do. Deep Pocket Guides consolidated everything and created a clear, powerful strategy. I finally feel in control of my future."

- Michael R., Beacon Hill, Boston

Is Your Retirement on The Right Path?

A 15-minute call can change your next 30 years. Find out where you stand with a free, no-obligation retirement review.

Book My Free Retirement Review