Solo to team struggles

If you're considering going 1099 as a stepping stone to growing your company with employees, you'll have to learn how to work through your employees.

As a solo 1099, if you have an idea, you just implement it yourself. No meetings or cajoling necessary. If you want to do it, you just do it.

If you hire an employee and want him or her to do something, you can tell them to do it, but you have to be clear about what you want and provide guidelines. Even so, they still might not be able to do it for various reasons (motivation, skills, etc.).

As you grow, you'll begin to appreciate how hard it is to run an organization that is bigger than just you, and maybe even appreciate some the things you hated about working for a big company.

If you find you hate leading and managing a team, you may discover staying solo is the right choice and perhaps you can achieve your bigger picture goals without hiring anyone.

However, if you DO like it and become more skilled as a leader and manager, I suspect you'll be able to accomplish way more than you could on your own.

Want the full playbook? Check out Going 1099.