How I Launched my Own Business — And Got my Boss to Pay Me to Do it

When you’re trying to get someone to do something they’ve never done before — let you begin working from home, job-share, take a sabbatical, work fewer days — the most important factor is: Does your boss trust you?

If the trust isn’t there, your chances of success are pretty slim. After all, if you’re not getting your job done while sitting 20 feet from your supervisor, why would they agree to let you work from home?

By the same token, if your boss knows you do what it takes to get the job done, you deliver consistently and on time, and are a team player, they’re going to be much more open to working with you.

As I mentioned above, I was up front during the hiring process about my intention to start my own business and eventually leave the company. While my boss wasn’t aware until I told him that the timeline had changed, I had never hid my intent from him.

That complete transparency won a lot of points, as he knew me as someone who was open and honest.

Also, over my years at the company, I met with my boss on a weekly basis, reviewing what I thought were my priorities and aligning them with what HE saw as my top objectives.

That meant that not only was I recognized as a hard worker, I was also seen as a major producer since the projects I worked on were the ones my boss perceived as high-value.

Because he trusted me and I’d built a reputation of integrity, I wasn’t hesitant to make a “big ask.” I had proven my worth.

If you’re a great employee, you may just need to up your visibility and tracking a bit. Start meeting with your boss more regularly to check in on his priorities and make sure you’re working toward those, not what you think he or she wants you to do.

If you haven’t been “Employee of the Month” material, now’s the time to adjust. Pay attention to the little things, like getting to work on time, turning in projects or assignments when you say you will, going above and beyond when you can, and in general being a superstar.

Bosses notice even the smallest shift in attitude and effort. See all of this as an investment in your future company.