I’ve been a freelancer, worked for two startups and currently work for an ad agency, and I definitely agree with most of the pros and cons you’ve laid out. I’ll tell you my experiences with each one.
Startups are great if you’re just starting out in your career. You will have to learn fast and fill multiple roles (I was the web guy, the graphics guy, assistant marketing manager). My advice here is that enthusiasm goes a long way, be pro-active by seeking out creative projects that will benefit the business, if you think the company website could be designed better, mock up another design and ask for time (or resources) to build it, or if the company needs new business cards, design some and get a quote on how much they will cost to print. No one will appreciate someone with passion as much as the boss of a startup, and you will have many opportunities to see your suggestions come to life.
After working for those startups, I decided to go freelance. This was the toughest gig for me because you have to go out and find your own clients, do your own taxes, chase clients down for money etc. For a creative this can be hard because we generally don’t want to be concerned with anything apart from the creative element…especially the boring admin stuff. It’s also an extremely lonely career path (unless you actively network with other design folk), and motivation can be a problem when working from home. I imagined a lot of freedom to be able to choose the projects I worked on, but my lack of clients made my options very scarce and I took whatever came my way. I realize a lot of this sounds negative, but I was totally unprepared for the amount of commitment needed to get my own business off the ground. My advice would be, if home is generally where you relax, never work from there. Ideally, get up early in the morning, grab your laptop and go to the nearest coffee shop with WiFi and work from there, or even better, find a shared creative space (there are many hot-desking hubs out there). Also focus on making an online presence for yourself (social media, Behance etc), get a kick ass portfolio together, and become an expert on one thing (a specific design style for instance). I’d love to give freelancing another go because I beleive it can be incredibly rewarding when done right.
After about a year working freelance, I decided I wanted to work as part of a team again. I found a job as a digital designer at a London agency for 3 years. The clients were all big names, and I’d be working on a different project each week. It was all really exciting, but if you don’t keep trying to challenge yourself on each project, you can end up churning the same stuff out again and again, which is just a waste of your time as a creative. It’s especially tempting to stay ‘safe’ because the pay is good, and there might not be a reason for you to take the any creative risks. My advice…don’t let yourself get stale! If you’re pitching, have a safe option, and a risky option, and see what the client is open to. Even if they don’t go with the risky option, it’s enough that you’ve challenged yourself to think outside the box.