Every bootstrapped business eventually hits capacity limits where doing everything yourself stops being sustainable — the question is whether the next step is hiring or outsourcing.

When outsourcing usually makes more sense

The need is specialized but not full-time — accounting, legal, design work done occasionally
You need the capability now but aren’t ready to commit to ongoing fixed payroll cost

When hiring usually makes more sense

The work is core to your business and needs deep, ongoing context that’s costly to rebuild with a new contractor each time
The workload is consistently full-time, where outsourced rates would actually cost more than a salaried hire over a year

Run the actual cost comparison, not just the gut instinct — outsourced rates can look expensive per hour but still be cheaper than a full-time hire once you account for total hours genuinely needed.