The phrase "to dip one's toes in the water" means to try something new or unfamiliar cautiously and hesitantly, usually to see if it is a good fit or to gain some initial experience. Full definition
She doesn't believe in dipping her toe in the water of experimentation, but rather jumping in and making the biggest splash possible. (bibliocrunch.com)
You can dip your toe in the water by reading an article or dive in and go back to college or get a master's degree. (happyselfpublisher.com)
Great entrepreneurs don't just dip their toes in the water. (entrepreneur.com)