Congratulations on making the decision to step away from the 9-5! You are at the forefront of a growing trend in product. A few years ago, it was difficult to find part-time and freelance product opportunities.

Today, more companies are open to the idea of hiring freelance PMs, and services like Toptal are helping to connect companies with talented product managers and product leaders. In addition, new services like A.Team and Squad Formers are enabling companies to hire entire squads. For freelancers, these services provide the opportunity to work with a consistent team of people without having to commit to a single company. People get the benefit of building camaraderie with a talented group of folks without having to commit to a single company.  

Up until a few years ago, I had a full-time job for my entire career. Every two weeks, I could rely on a consistent paycheck. Making the jump to "1099 life" (the US tax form received by freelancers) requires a little courage and preparation. 

1 - Build some runway

First, you should build some "runway". It takes time to replace your full-time income and its helpful to have 6-12 months of cash set aside to give yourself some cushion.

2 - Make a plan

Secondly, it's worth doing some planning. What types of freelance roles will you focus on? In an ideal world, how much should you charge and how should you package your services? For example, I started with an hourly rate for coaching services, but quickly found that it was better to offer a monthly retainer. During this step, it's really helpful to talk to other folks who have recently started freelancing to get an idea of the market.

Note, I'm assuming you want to start with freelance product roles. Even if you want to generate other income streams (for example, by selling digital products, offering courses, or building a community), it's helpful to start with freelancing. This is the quickest way to begin replacing your income and will help you explore what the market wants. 

3 - Spread the word!

Third, raise your "open to work" flag! Let everyone you know that you are open to freelance opportunities, and ask people for intros to people who may be hiring. You may even be able to negotiate a freelance opportunity with your current employer. Many people are surprised how quickly they land their first paid gig. 

At this point, it's helpful to be flexible on rate. I took my first consulting gig at less than 1/3rd the rate I'd eventually charge. I was also open to working for equity if I knew that I would learn a lot and the role was a jumping off point. 

These early days are the toughest. Its tempting to look at what you are making from your first gig and compare it to your old salary — often fondly remembering those big, consistent bi-weekly pay checks. Don't be too hard on yourself. It's initially hard to replace your salary, but eventually easy to leave that salary in the rearview mirror.

4 - Build your brand

Fourth, start writing, podcasting, or creating video content. You are now your own employer, and great employers have great brands. Freelancers with a brand & an audience are much more likely to be successful over the long-term. 

It may seem daunting at first. But, remember that you are uniquely great at certain things and there are always underserved topics to cover. For example, today there are PMs breaking through the noise with smart content about ML, the creator economy, product-led growth, and Web3. 

In addition, you don't need a million followers. You need to create a presence that shows off your best thinking — if you do, you'll always get the job over another person who hasn't put their ideas out there.

5 - Generate passive income

Lastly, start exploring passive revenue streams. Remember, you wanted to escape the 9-5 to get time and balance back in your life. Freelance work is great, but it is still a matter of trading time for money. The most successful freelancers have multiple sources of income, and often seek to shift from active to passive income. Jack Butcher is a designer, creator, and thought leader who has written a lot about his journey. His story is inspiring, and he offers tools to help people on a similar path. Worth checking out.

Oh, I almost forgot. If you are in the US, taxes look really different for 9-5 employees vs. freelancers and small business owners. A company like Collective is great with helping you make sure your freelance business is setup to maximize your earnings. 

Good luck on your journey. There are risks, but also significant rewards. Over time, you'll build a base of skills, network of relationships, portfolio of projects, sources of income, and reputation that compounds from year-to-year and doesn't reset from job to job.

Many people find that a risky decision to leave their job is the most secure career decision they've ever made.