Retirement and Financial Planning

Retirement is not a finish line — it is the point at which your wealth, rather than your paycheck, funds your life. Getting there, and staying there, requires more than a good portfolio. It requires a written, coordinated financial plan that connects every dollar you save, spend, protect, and transfer to the goals that matter most to you and your family.

At Great Point Wealth Advisors, comprehensive financial planning is the foundation of every client relationship. Investment management, tax planning, insurance, estate design, and cash flow are not separate services — they are the outputs of a single planning process we run for you and update for the rest of your life.

The CFP Board's Seven Steps of Financial Planning

Our planning process follows the Seven Steps of Financial Planning established by the Certified Financial Planner Board of Standards. These steps are the professional standard of care for CFP® professionals working under a fiduciary duty, meaning your interests come first at every stage.

Step 1 — Understand your personal and financial circumstances

Before any recommendation is made, we build a complete picture of your financial life:

• Family & goals context — household composition, dependents, health, career stage, business ownership, expected inheritances, philanthropic intent
• Balance sheet — every account, property, business interest, private investment, and liability, including held-away assets we do not manage
• Cash flow — earned income, deferred compensation, RSU/ISO/NSO grants, K-1 distributions, pensions, Social Security estimates, and recurring outflows
• Tax situation — recent returns, marginal and effective rates, carryforwards, AMT exposure, state residency
• Existing documents — wills, trusts, powers of attorney, health care proxies, beneficiary designations, insurance policies, buy-sell agreements
• Attitudes & preferences — risk tolerance, values, time horizon, liquidity needs, ethical or religious constraints on investments

This is the "data gathering" step, and it is deliberately thorough. Everything that follows depends on getting it right.

Step 2 — Identify and select goals

We help you articulate what you actually want your money to do, in specific and prioritized terms:

• Retire at a defined age with a defined after-tax income
• Fund education for children or grandchildren
• Purchase a second home, boat, or investment property
• Sell or transition a business
• Support aging parents
• Fund a specific charitable legacy or family foundation
• Leave a defined inheritance to heirs

Vague goals produce vague plans. We convert "retire comfortably" into a dollar figure, a date, and a probability we can measure.

Step 3 — Analyze your current course of action

We stress-test where you're headed today. Using cash-flow and Monte Carlo modeling, we quantify:

• Probability of funding retirement at your desired lifestyle
• Sustainable withdrawal rate through market cycles
• Sequence-of-returns risk in the years surrounding retirement
• Exposure to inflation, longevity, health care shocks, and tax-law changes
• Concentration risk in company stock, real estate, or a private business
• Whether existing insurance, estate documents, and beneficiary designations still match your life

You see, in one place, the gap between your current trajectory and your stated goals.

Step 4 — Develop financial planning recommendations

We build a written plan that addresses each area below. Because they are interconnected, we solve for them together rather than in silos.

Retirement income design

• Target retirement date and after-tax spending
• Social Security claiming strategy across a marriage, including survivor considerations, using tools consistent with SSA guidance
• Pension election (lump sum vs. annuity, single-life vs. joint-and-survivor)
• Roth conversion strategy during low-income years
• Required Minimum Distribution planning under current IRS rules, including the SECURE 2.0 age-73/75 provisions
• Withdrawal sequencing across taxable, tax-deferred, and Roth accounts

Savings & contribution strategy

• Maximizing 401(k)/403(b), IRA, HSA, and after-tax "mega backdoor" Roth contributions when available
• Defined benefit and cash balance plans for business owners
• 529 plans and, where appropriate, 529-to-Roth rollovers under SECURE 2.0
• Non-qualified deferred compensation election strategy
• Systematic saving from cash flow, calibrated to leave a resilient emergency reserve

Investment management

• Written Investment Policy Statement covering target allocation, permitted ranges, and rebalancing rules
• Broad global diversification across U.S. large, mid, and small cap, developed international, emerging markets, and high-quality fixed income
• Predominantly low-cost ETFs and institutional share classes to minimize expense drag
• Asset location: tax-inefficient assets in tax-deferred accounts, tax-efficient equities in taxable accounts, municipals where they improve after-tax yield
• Tax-loss harvesting and gain-budget rebalancing in taxable accounts

For the full investment framework, see our Cash & Investment Management page.

Tax planning

• Multi-year projections rather than single-year filing
• Roth conversion ladders and "fill-the-bracket" strategies
• Harvesting of capital losses and, where beneficial, capital gains
• Qualified Charitable Distributions from IRAs after age 70½
• Donor-advised fund bunching strategies
• Coordination with your CPA on quarterly estimates, entity structure, and state residency

Insurance & risk management

• Life, disability, and long-term care needs analysis
• Property, casualty, and personal umbrella review
• Health insurance and Medicare planning, including IRMAA management as retirement income shifts
• Business insurance including key person, buy-sell funding, and professional liability

Executive compensation & concentrated stock

• ISO/NSO/RSU/ESPP timing and tax modeling
• 10b5-1 plans for insiders
• Diversification strategies for concentrated positions, including exchange funds and completion portfolios
• 83(b) elections and QSBS (Section 1202) planning for founders

Estate & wealth transfer planning

• Wills, revocable trusts, powers of attorney, and health care directives
• Beneficiary designation audits across every retirement and insurance account
• Lifetime gifting using the annual exclusion and lifetime exemption
• Irrevocable trust strategies — SLATs, ILITs, GRATs, IDGTs — where appropriate for your net worth
• Generation-skipping planning and dynasty trust design
• Charitable remainder and lead trusts
• Massachusetts-specific estate tax planning given the state's $2 million exemption — a common trap for Boston families

Business owner planning

• Retirement plan design (Solo 401(k), SEP, SIMPLE, cash balance)
• Succession, buy-sell, and exit planning
• Reasonable compensation and S-corp distribution strategy
• Sale proceeds reinvestment, including Qualified Opportunity Zone options

Education planning

• 529 funding levels calibrated to expected cost
• Grandparent-owned 529 strategy under the current FAFSA rules
• Coordination with financial aid, scholarships, and merit-based awards

Step 5 — Present the financial planning recommendations

We deliver the plan in writing and in person. You see:

• The specific recommendations and their rationale
• The order of operations and who is responsible for each action
• Expected outcomes, including updated probability of success
• The cost of implementation — trading, tax, and advisory fees — before anything moves

Nothing is executed until you understand it and agree with it.

Step 6 — Implement the financial planning recommendations

We take ownership of getting the plan into place:

• Opening and funding accounts at Fidelity, Charles Schwab, TIAA-CREF, or other third-party custodians
• Coordinating transfers, position reconciliation, and cost basis updates
• Placing trades in tax-aware sequence
• Working directly with your CPA and estate attorney, or introducing you to trusted professionals in our network when you don't have one
• Filing beneficiary changes and updating account titling

You retain full control — accounts remain in your name under a limited power of attorney, and your custodian sends statements directly to you.

Step 7 — Monitor progress and update

Financial planning is not an event. We:

• Review portfolios continuously and rebalance as markets or life warrants
• Meet formally on the cadence you prefer, typically annually or semi-annually
• Update the plan whenever a material event occurs — job change, business sale, marriage, divorce, birth, inheritance, death, relocation, or a major shift in tax law
• Provide a Quarterly Market Review so you stay informed between meetings
• Remain available for unlimited interaction — the meter is not running

Planning across your stages of wealth

The seven-step process is constant, but its emphasis shifts as you move through the stages of wealth we describe on our homepage:

Emerging wealth. Cash flow discipline, aggressive tax-advantaged savings, appropriate risk-taking with a long horizon, and getting the foundational documents in place.

Independent wealth. The transition into "your money funds your life." Withdrawal sequencing, Roth conversions, Medicare and Social Security decisions, and preserving purchasing power against a 30- to 40-year retirement.

Generational wealth. Efficient transfer to the next generation and philanthropic goals. Trust design, gifting strategy, and preparing heirs to be good stewards.

Why the process matters

A written plan does three things that ad-hoc advice cannot:

1. It makes trade-offs visible. Every dollar spent, saved, gifted, or invested is competing with another goal. The plan quantifies the trade-offs so you can choose deliberately.
2. It coordinates specialists. Your CPA, estate attorney, insurance agent, and investment advisor each optimize their own domain. The plan ensures they optimize for the same client — you.
3. It removes noise. Markets, headlines, and tax proposals will move constantly. A written plan is the reference point that keeps decisions rational.

Starting the conversation

If you would like to see what this process looks like applied to your situation, we invite you to submit an inquiry through our Contact page. The first conversation is a brief phone call to determine whether an introductory meeting would be mutually beneficial. There is no cost or obligation for the initial meeting, and no reference is made to your accounts or documents until you decide to move forward.

Great Point Wealth Advisors is an independent, fee-only Registered Investment Advisor. This page describes our general planning approach. Every engagement is customized to the client's circumstances, goals, and written Investment Policy Statement. Nothing on this page constitutes tax, legal, or investment advice for any specific person.