I've been bootstrapping my own startup for about 12 months. IMO if you take a day job, you're sufficiently distracted to fail. I'm not sure how far down the entrepreneur path you are, but you'll realise that launching your own startup will take every hour you have. You'll work harder than ever - and you'll want to, because this is your idea. I sounds like you have accrued some skill and knowledge, so I would recommend consulting your expertise out to others. This let's you stay in control of your time, you pick the projects. If you can work on projects that are time flexible, then even better. If you can work in an area that also ties into your startup, then you're winning. IMO your "career progression" is what you learn from the entrepreneurial experience. To succeed, you need to put in 200% and the key is to make mistakes and make them quickly. If it all doesn't work out, then you can quickly get back to looking for a good job at a good company.