There’s three approaches I use here.

1. Find some bit that you bonk your head into regularly. Maybe it’s query optimization. Maybe encryption or auth. Maybe infra setup. You can usually muddle through it by reading the 5th comment on SE or finding a coworker’s working code. But you don’t actually understand how or why it works.

2. Think more broadly of where you want your career to be in 5 years, or what you want your next job to be. Map out what you know and what you need to know to be successful in that role. Study the gaps. Sometimes it’s not technical skills.

3. Pick a project you find interesting that has nothing to do with your current job responsibility. Frontend? IoT? Systems level stuff? Dig in! You will find that unrelated computer stuff is in fact all related in some way.

The least adventurous approach is to work at the edges of what you’re already doing. Are your apis usually consumed by react components but you’ve never written one? Try writing a react app that consumes one of your services and see where the pain happens. Even if you never use react again you’ll have learned something about your work from a new perspective.

Don’t spend too much time on anything that isn’t fun. Chase joy and fail fast.

Hi, fortune 200 employee here

Each company has its own procurement process for contractors so ymmv. It’s challenging to get a foot in the door at Enterprise orgs because there are typically a few factors that you might not think of if you haven’t already done work for them.

1. the people making selections have to know you exist. This is frequently achieved via direct contact: calling or emailing with a free demo of your product or service. You may not always be talking to the person who makes the decisions but you might find mid- to senior-level engineers or managers who can influence the decision. Presence at tradeshows is also a big way to get exposure. Knowing people in the org can be a huge advantage
2. there are invisible standards you might have to meet. Often procurements take months to years to work out with legal, privacy controls, and architecture standards evaluations. We just hired a company to deliver some imagery over a 3 month period and the contract took almost 3 months to get resolved. You may need to carry special types of insurance depending on the industry of the company that would hire you. One company I worked for had a list of approved vendors at varying statuses of what they could and couldn’t work on.
3. for the reasons above, it’s usually wise to have a dedicated sales person who can make contacts and schedule demos, may already know people in the industry, and knows how to work those contacts into referrals. This person ideally also knows how to navigate the corporate/regulatory framework to make sure you have the right secret handshakes.

Hope you find this helpful and good luck

I was mostly a lurker there, I’ll be mostly a lurker here too.