I found it easier to grow my hair out kind of in stages, so I would keep the back and sides a little cleaner until the top was longer then I just trimmed the top when it got too long until everything caught up and my hair started sitting naturally
Find a stylist you like and tell them your plan. Go in every 3-6 months for a cleanup/shaping and wear a hat/bun when it’s in the awkward phases. That’s what I did and it was fine (except for the one time a substitute gave me a bob lol).