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Retirement turns one paycheck into many. Social Security gets sequenced against portfolio withdrawals, Roth conversions, pension income, required distributions, and the timing of when each source begins. The work is sequencing the income across decades.
Our plan adjusts at every stage: when Social Security starts, how Roth conversions are timed, which account funds each year's withdrawals, and how spending shifts in late retirement.
401(k), 403(b), Traditional IRA, Roth IRA, Rollover IRA, taxable accounts, pension if there is one. Each carries different tax treatment, different withdrawal rules, and different roles inside the retirement plan. The work is using each one for what it does best, rather than running them as separate buckets.
Retirement isn't a date, it's 25 to 40 years of changing conditions. The plan gets tested against bad market scenarios, accelerating healthcare costs, tax-law changes, and longevity beyond what the household expects.
Social Security, pension elections, IRA withdrawals, Roth conversions, RMDs, and portfolio sales each carry their own tax math. Pulled in the wrong order, they push the household into brackets it didn't have to enter. The plan sequences each source against the bracket math, year by year, across the whole retirement.
Early retirement, mid-retirement, and late retirement each have their own math. Spending looks different across the stages, medical costs rise, RMDs activate at 73, and surviving-spouse brackets change. The plan gets reopened as each stage arrives.
Before any retirement math, there's a real conversation about where you are and what's coming. Sometimes that's a five-year horizon, sometimes a few months, and sometimes in the midst of retirement already where you're finding the math harder than expected. By the end you'll know whether this fits and what the planning involves.
Every income source and every spending obligation that retirement has to balance: Social Security records, pension statements, 401(k) and 403(b) balances, IRA balances by tax treatment, taxable accounts, real estate, expected inheritances, and equity grants still vesting. On the spending side: current spending, expected retirement shifts, dependents, debts, and healthcare history.
The plan models income across decades against the spending it has to cover. Social Security claiming strategy, Roth conversion timing, account-by-account withdrawal sequencing, RMD planning, and IRMAA-aware tax brackets all run through a single set of projections. Trade-offs surface explicitly: a conversion now means lower RMDs later, an earlier Social Security claim means a lower lifetime benefit, larger portfolio draws early mean more sequence risk.
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The first year of retirement is when the plan goes live. The Social Security filing gets timed; the Roth conversion ladder starts; direct distributions begin from the right accounts in the right order; beneficiaries on every retirement account get reviewed and updated; and Medicare enrollment moves on the schedule the plan requires.
Each retirement year reopens specific decisions. Roth conversion windows close at 73 when RMDs begin. Markets move and reset the spending math. A spouse passes and the tax brackets, Social Security, and inherited account rules all change at once. The work follows the stages as they arrive.
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Retirement is the longest single phase of a financial life. The senior advisor who designed the plan is the same person making each year's calls when they come. The advisory is there at every Social Security timing, Roth conversion window, spending re-projection, and surviving-spouse adjustment.
Our advisors keep concentrated client books so the senior advisor stays close to the math across every retirement year. When a decision crosses into tax, estate, or investment management, the specialists are in-house and one conversation away.
Rob works with founders, executives, and families navigating concentrated wealth, business exits, and generational planning. He founded Arrowroot in 2013 and leads the firm from Southern California.
Cassandra works with clients on retirement planning and Medicare strategy, with deep expertise in healthcare cost planning and the tradeoffs that shape later-life decisions. She is a licensed insurance agent with more than 12 years in financial services.
Crystal works with individuals, families, and business owners on financial planning, investment management, and tax strategy. She is a CFP® and IRS Enrolled Agent with over two decades of experience.
Irene oversees operations and regulatory compliance across the firm. She brings more than 22 years of financial services experience across investments, capital markets, operations, management, and sales.
Mark works with families and business owners on financial planning, portfolio management, and tax strategy, with a particular focus on cash flow and long-range projections. He is a CFP® and IRS Enrolled Agent.
Diane works with individuals, families, executives, and retirees on retirement planning, investment strategy, and long-term wealth management. She is an Accredited Investment Fiduciary® with over 30 years of experience.
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Building a business creates a personal wealth situation the business itself won't manage. Concentration in the company, deferred compensation, an eventual exit, and the retirement that follows each carry their own math. Decisions on the company side get coordinated with the personal plan so the two sides move together.
Threads through every investment decision and every estate document. Tax efficiency depends on timing as much as choice. Decisions get made so the math holds up across decades rather than quarters.
Built around the obligations the portfolio has to meet. Holdings fund retirement income, education, gifting, and the unexpected on schedules that match real life. Risk gets calibrated to the work, and tax planning runs through every position.
At the center of cash flow, tax, and investment decisions, this long phase has its own math at every stage. Income, taxes, and sequence get modeled so the timeline holds up under stress. The work continues across every transition retirement contains, since one phase rarely sets the pattern for the next.
Touches every other practice the moment something changes. Estate, tax, and investment positions stay aligned so the structures still work when the time comes. Documents get revisited as the family and the assets shift.
Protects what's been built when something happens. Coverage gets sized to real exposure across business interests, dependents, and estate liquidity. As obligations shift, coverage shifts with them so the protection matches the situation.
Stock from your employer carries three identities at once: a tax position, an investment position, and a concentration risk. Vesting, exercise, sale, and AMT decisions get weighed together rather than separately. Timing of each gets coordinated against the broader picture.
Financial Planning is the practice that integrates the others into one plan. Tax decisions get made with investments in view, estate work gets shaped by the cash flow strategy, equity compensation gets calibrated against the rest of the picture. The plan holds together because one advisor guides it.
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Tell us where you are, where you're headed, and what you're working with. We'll help you get there.
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