
Let's not be too harsh: freelance checks for essays and speaking engagements, which don't automatically deduct Social Security and payroll taxes, are treacherous, treacherous things—all the more so if you're doing well, and owe upper-bracket percentages (I assume). Still. Would you vote for a Congressional candidate who explains his messy finances by reminiscing about his impoverished boyhood and lifetime of poor money decisions on the Huffington Post? (I like the part where he blames his mother for not giving him any concrete financial advice.)
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