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Transitioning from Solo Expert to Business Owner – Whom to Hire First?

Many freelancers or solopreneurs think about expanding their work into a business venture someday. Many, at least try, and some actually realize their dream.

Transitioning from freelancer to business owner involves numerous tasks and significant changes. This post aims to talk about hiring and approaches you can take.

Hiring juniors or interns.

Hiring interns or junior-level helpers at a low cost is often the first step many take when moving from solo work to team-based work. Especially in self-funded setups, this approach is common due to its lower financial burden. Interns can often be found with minimal effort and short lead times.

However, training them takes time. Without a clear plan for mentorship, juniors may struggle, underdeliver, or leave early. Their output may affect timelines or quality if not closely supervised. There’s a risk that, instead of saving time, the workload increases. Simply treating interns as cheap labor tends to backfire unless there’s readiness to invest in their development.

Hiring someone smarter.

Choosing to hire someone more skilled or experienced is a different kind of move often a strategic one. This route appears more common when the goal is to improve creative quality, scale faster, or delegate leadership responsibilities.

Though this option comes with a higher cost and sometimes emotional challenges around hiring someone more capable. It often leads to stronger long-term outcomes. It may require higher pay or revenue sharing, and a shift in how leadership is viewed. In these cases, the founder’s role moves from doing everything to guiding, enabling, and removing obstacles for others.

Interestingly, high-talent individuals tend to attract more talent. When skilled people are brought in early, they often shape the team culture and help draw in others of similar quality.

A hybrid approach?

A pattern observed in some of the most successful transitions is a hybrid path. Hiring one highly skilled person first, even at a higher cost, to help set up strong systems and processes. Once that foundation is in place, junior hires can be added and trained within a more stable structure.

In most cases, the first few hires define the direction, quality, and culture of the team. Whether the goal is scale, quality, or freedom, those early decisions tend to echo throughout the future of the business.

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Rasan Samarasinghe

A multifaceted professional known for diverse interests and contributions in various fields, including management, technology, education and entrepreneurship. Also the founder of ITPro.lk, bringing a unique perspective and industry knowledge to writing.

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