Career development and goals for freelancers?

I'll bite... 🙂

Some really good questions. Here are my thoughts (my own experience and research for a project that I'm working on)...

1. Planning - depends a lot on nature of the work (eg., photographer with a couple of days shoot vs web developer with a month long project). Also depends on current projects and timelines. So it is definitely hard to plan 6-12 months down the line. What you can do is keep your network constantly posted on your availability so that the work keeps coming in. Also build a network of sub contractors to outsource excess work and not get into a position of saying no to clients
2. I used to setup monthly goals and review. As a freelancer, goals are generally business oriented (revenue) but I used to have separate study goals and side projects also which I used to track
3. I wasn't in it long enough to be in a position to decide between lucrative vs career goals but I'd prefer lucrative projects as that determines market demand. As a freelancer, you've implicitly changed your career goal to building a business, so favour the market and be flexible. If you have specific work that you love to do, then figure out higher value messaging and search for lucrative projects in that space. This takes time
4. Yes, regular reviews of my progress helped but I'd love to have a mentor
5. Progress validation - review with the goals I set
6. Levelling up - 2 types - scale and skill. Scale means getting bigger and more value projects which you can't execute by yourself. So it needs you to build a network (which you should be constantly doing). Skill is dependent on market (eg., you might be a web developer but the market is moving more towards mobile apps) and your interests. What is important is understanding these dynamics, setting goals and sticking to your plan. But you do reach a limit when it comes to how much you can do on your own (and hence the size of projects), so it is very important to build a network
7. Getting "new skill" projects - take part in the communities related to the new skill to understand the current trends, do some personal projects that you can showcase and get it peer reviewed, update your marketing content to include this new skill, reach out to your regular clients for work in that new area (offer to work at a lower price while you "level up")
8. Yes, performance reviews help, especially when you are on your own as a freelancer

One of the reasons I used to go back to job after freelancing for a bit is that I felt a little directionless after a while. Job sets up a nice path to grow. This can be done with freelancing also but like with everything else in freelancing, you have to figure it out yourself and that's both challenging and exciting.

4 things I recommend to have long term career in freelancing...

1. Take part in local/online freelance communities
2. Build a network of folks that you can collaborate with
3. Have actionable goals that you can keep track of and plan to work towards them
4. Keep working on your skills, ways to upsell and creating a constant inflow of work

BTW, this question might get better traction on https://www.reddit.com/r/freelance.