Work Wonders

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What I wish I knew before leaving my 9-5

More than ever, professionals are curious about leaving their 9-5. Freelance life, contract work, and self-employment - which used to feel too risky for many of our clients - is increasingly an area that many want to explore.

As someone who made the leap out of my day job a few years ago, I thought I would share a few lessons learned from my own experience as a self-employed person and as a portfolio careerist.

Here’s what I wish I knew before leaving my 9-5:

  • How much time it would take to replace my income through self-employment. While the internet is filled with people who replaced their income in six months or overnight, I can’t say the same. Figuring out my exact services, balancing revenue with work-life balance, and growing a team are all things that have taken (and continue to take) time. 

You may know that I continued to teach as an adjunct instructor as a side gig and this definitely provided the continuity and income that allowed me to pay my bills, save for retirement, travel, and do the work I wanted to do through my business.

If you’re having a hard time imagining a business or freelance career that can replace your income, consider a supplementary line of work that may be able to either serve as a bridge or help you take the pressure off needing to earn your income exclusively through your business.

  • How important referrals are. When it comes to marketing your business, you’ll have plenty of options. Maybe too many! I wish I had known about referrals and doubled down on a referral-based strategy way earlier.


So many of my peers generate the majority of their business through referrals! If you can’t imagine marketing yourself or where the business will come from, please know that it often comes from actually doing the work and having relationships with friends, colleagues, and fellow business owners.

It can seem like a black box from the outside, but one book that we recommend to clients is Get Clients Now! By CJ Hayden. It’s a super simple way to practice consistency in your marketing and it won’t take you down a rabbit hole that requires you to be internet famous to be successful.

  • How nimble I could be with my budget. Something that has surprised me is how far my money now goes. And how much more I value my freedom and autonomy above all else, including maximizing my earnings.

When I left my job, I had student loan payments of over $700/month. I also live in an expensive city. I’ve never been in a position where I didn’t have to earn a decent living because my baseline expenses are fairly high!

Working from home, I’ve learned to appreciate my mid-day walks and being able to prepare meals throughout the day. I no longer blow $20 grabbing lunch in the city. 

Our clients know that I’m a huge YNAB fan. It helped me get my finances together so that I could leave my full-time job and manage my finances once I shifted into a new compensation model with ebbs and flows. If you’re not a user, I highly recommend it. It can really help you watch your money, identify patterns and change your financial behavior. I’m a huge fan!


Are you thinking about leaving your full-time job? What kind of questions do you have?

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