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Work. Better.

Career Pivots

How solopreneurs should prepare for long-term leave — before they ever need it

A practical guide to planning for the worst.

Anna Burgess Yang's avatar
Anna Burgess Yang
Jan 04, 2026
∙ Paid
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Most solopreneurs don’t think about long-term leave until they’re already in crisis mode. A major illness. A family emergency. Or even a planned event like parental leave. And yet, every solo business — regardless of industry — faces the same vulnerability: when you step away, the entire business pauses with you.

When I first started my solo business three years ago, I wondered, “What would happen if I got really sick and couldn’t work for a few weeks?” If I don’t work, I don’t get paid, so I always knew this was a risk.

Never in my wildest dreams did I think “brain tumor,” but that’s what I was diagnosed with earlier this year. Suddenly, I was faced with the reality of stepping away from my business for months, not weeks. I had about six weeks to prepare between diagnosis and surgery.

The truth is, operational readiness matters far more than we assume. And the time to think about it is long before you need to.

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