You’ve done a lot right: steady saving, sensible investing, low drama. What’s left isn’t starting over; it’s tightening the coordination so taxes, investments, estate, and college/retirement decisions work together instead of in parallel.
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Many accounts, little integration: investments, company stock or pensions, IRA, 529 accounts, and old 401(k) balances are organized but not coordinated.
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Annual taxes, not year-round planning: taxes get filed on time, but asset location may not be tax-smart; Roth conversions and gain/loss harvesting can get missed.
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Time scarcity: prioritizing time for finances is hard without a clear task or someone quarterbacking.
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Possible inheritance—but not the plan: you expect to receive some money in the future, yet want your strategy to stand on its own if it doesn't arrive.
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Multi-generation pull: you're balancing kids’ education funding, evolving parent-care needs, and keeping your own retirement and lifestyle on track.
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Dated estate plans: it has been a while since anyone reviewed the wills/POA/beneficiaries, and Massachusetts estate tax can sneak up at $2M.