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Abstract When comparing investment in an immediate life annuity with a payout-equivalent investment fund decumulation plan (self-annuitization), previous research focused on shortfall probabilities of self-annuitization. Chances of self-annuitization (i.e., bequests) typically have not been addressed. We argue that heirs might be willing to bear the shortfall risk of the retiree's self-annuitization since they might benefit from a bequest. Our article proposes a “family strategy” in which heirs receive the remaining investment fund on the retiree's death, but are obliged to finance the retiree if the fund becomes exhausted. We estimate the chance and risk profile of this “family strategy” from the heirs' perspective using German capital and annuity market data. We show that in many cases, our “family strategy” offers enormous chance potential with low shortfall risk. Finally, we discuss some limitations of the proposed “family strategy” when putting the concept into practice.