What to Do When You Know You’re Ready to Take Your Side Hustle Full-Time

October 8, 2020

Photo of hands on a table, holding pens and notepads.

So you want to take your side hustle full-time?

Maybe you’ve hit the last straw with your supervisor from hell or you happen to be one of the lucky ones for whom a separation from your great day job is bittersweet. Either way, there are a few things to keep in mind before you submit that two-week notice.

Note:  Everyone’s transition from a J.O.B. to full-time self-employment will be different. Depending on your side hustle the nature of your retirement, financial circumstances, and other "adulting" matters, please consult a legal or financial expert before storming out of the lobby and flipping the bird to your boss.

Are you ready to take your side hustle full-time?

Document All of Your Business Expenses

The world of self-employment and entrepreneurship is overflowing with infomercial-like shiny objects and tools that will claim to be the thing you need to solve all your problems, especially if your side hustle will be primarily run virtually. While it may only be you and your partner handling all the day-to-day activities, you’re eventually going to need some help. You’ll need to outsource things to an assistant like book keeping, scheduling social media content, updating blog posts for SEO, or possibly an extra set of hands to adhere shipping labels and bring online orders to the post office every week.

Once you quit your job, the word “income” will take on a whole new meaning. No more Friday paychecks (unless you set that kind of that system up for yourself!) Unfortunately, for many newly-launched business owners, planning for your income quickly devolves into a penny-pinching, bootstrapped mindset. You somehow convince yourself that you just. Can’t. Afford. To Spend ANYTHING. Too many fees! 

To avoid becoming that kind of boss that you hate working for (who else hates hearing their supervisor talk about limits on expensing?) keep a record of all your expenses from the get-go, including the ones you binge buy off of Appsumo. A simple Microsoft Excel or Google Sheet will work just fine!

Include everything on that list (and include a date column so you can anticipate annual renewal fees!) so that you know exactly how much your business costs you:

  • Domain registration & hosting
  • Graphic design software
  • PO Box fees
  • Business license renewals
  • Bookkeeping software
  • Office Supplies & postage
  • Professional networking association fees
  • Social Media Scheduling Software
  • Fees for printing, scanning, copying

Tell Your Family and Loves Ones Before You Quit Your Job

Have you told your family what you’re building? Do they know all about the legacy that you’re creating with your business? 

We all dream of the “Surprise! I told you so!” scenario where you’re secretly making 5-figures every month, your partner stares in awe at your meticulously perfect profit & loss printouts and has no choice but to acknowledge what an amazing and lucrative side hustle you’ve created, all on your own.

Spoiler alert: It will be a lot easier to do this WITH them than without them.

Now, not all partners and families are supportive. In fact, if you’re a multi-passionate person with a positive attitude, who sees tremendous opportunity at every corner, our cynical, capitalist world hasn’t wired everyone to think the way you do.

But if this business really means that much to you, and if your family and your community play any part in your big “Why,” then get them involved sooner rather than later. They don’t need to be hands-on, in the trenches with you (although if they are, that is frickin’ amazing! Talk about bonding time!), but they should know what you’re doing every day when you're glued to your laptop on a Zoom call again.

This is your passion. It’s your legacy. It’s your calling. It’s intended to benefit them, anyway, right? If you truly intend for this to be a heart-centered, self-sustaining business that gives you the freedom you’ve always wanted, have a conversation with your loved ones and tell them what you’re building.

Establish Reasonable Back-End Processes and Workflows That Are Easy to Manage

Remember the pile that the HR manager flipped through on your first day, and how you were given certain sheets to keep for your records? How about the “Manual” binder in the office that no one ever references because everyone just creates their own shortcuts? 

One of the funny things about having a self-sustaining business is that a lot of the redundant documentation at the office still needs to happen when you’re self-employed. There are a lot of things you don't want to replicate in your business (toxic work culture, business casual blazer jackets, mandatory 40+ hour work weeks, etc.) but the documentation? Yep.

This is technically a two-part requirement: 1) You need to have efficient back-end systems for any repetitive tasks you do, and 2) You need to have them documented because those processes will be the first things to hire out when you scale.


After years of working behind the scenes in multiple businesses as a tech VA (technical virtual assistant) and a PM (project manager), I can share with confidence that this is easier than you’re making it out to be.

You may be like some of my clients and exclaim, “Oh my gosh! I don’t have any processes! I’m a mess!” but trust me, you’re doing fine. Your brain may not be wired to see things systematically (hello, visionary!), and that’s totally okay.

Processes are the tasks you tend to do repeatedly. These could be:

  • Emailing or texting reminders about meetings 24 hours in advance
  • Responding to commonly asked questions with the same blurb or reference to a specific blog post
  • Always using a certain color “green” and never using a certain font in your graphics
  • Always including alt-text on Instagram because you care about accessibility

Or simply the way you prefer to do things, personally. 

Think about how you batch your social media content. Do you always take your photos at sunset? Do you wait until a certain week of your menstrual cycle to write your blogs, because that’s when the ideas and words come more naturally to you? Do you have a rule about never checking your email before 11:00am?

You've got a process and good reason for it. Keep track of it!

Create a series of digital documents that outline how you run your business. I recommend using a Google Drive, creating a folder called “SOPs” (Standard Operating Procedures), and separating each process into its own document so it’s easy to reference.

When you’re ready to hire help, you should be able to have a training session with them. That meeting will go smoothly if you have a central place where all processes are already documented. This makes onboarding easier for both of you, since your new recruit will be simultaneously learning from you and performing work for you.

See a Mental Health Professional & Triple Check Your Confidence and Self-Esteem

Are you a first-generation entrepreneur or business owner? Maybe you come from a line of chemists, doctors, and engineers, and you’re the cousin in the family who went down a different path.

When I’m asked about the ONE piece of advice I’d give to someone who’s considering taking the plunge and becoming a full-time self-employed person or entrepreneur, my answer is always the same:

See a therapist, first.

I’m not trying to imply that you’re wrong about your passion or that you’re mentally unstable.

In fact, I think everyone (including me!) should be seeing a mental health professional at all times. You can have the most supportive family and the best of girlfriends, but we all need a non-attached third party who's trained to help us keep our clarity about our life, our dreams, and our goals.

In hindsight, I know that when I quit my day job, there were other things about my life I was hoping that decision would “fix.” It’s easy to assume that your job or your boss are the only thing keeping you from living your best life. In reality, a vocation or a certain person at the office have very little effect on how happy you are with your life.

Unless you were raised by mindset-focused, entrepreneurial-minded adults, you’re in for a reality check when you wake up on Day 1 and the only person you have to answer to is yourself. 

While entrepreneurship and self-employment are growing steadily and becoming fairly common, our society for the most part is built to support the typical (white) American dream: Get a corporate job, climb the career ladder, have babies, buy more things than your peers.

We’re not nurtured to learn more about ourselves, critically self-evaluate, or think independently.

To give you a preview of what might bubble up for you (from my own experience of quitting prematurely):

  • I don’t know enough (or what I knew has run out, and I’m out of options)
  • I’m doing this because I’m trying to prove something to someone (my boss, my dad, my aunties/uncles, my coaches)
  • I am fundamentally lacking what makes other people successful at what I want to do (and my income must be proof of this)
  • I’m mentally unstable (and paying for my own health insurance, so this is going to be expensive to fix)
  • I thought I knew what I was doing but I don’t believe in myself anymore

All of these thoughts, while brought into view by the isolation and sometimes brutal nature of self-employment in our “everyone should stay in their corporate positions for security” society, were already there before I quit my job. It would have been a lot smarter for me to unearth them with a professional prior to quitting (preferably with my vastly-superior health insurance from my job compared to the medical coverage I got independently) than while I was simultaneously finding my purpose, creating a brand, making a living, working from home, mending rocky family relationships, and also trying to live a normal live in my 30s.

See a therapist first, folks. Worst case scenario is that you use all the sessions included in your health coverage and your therapist gives you the thumbs up to go ahead and quit.

Know Whether Your Business’ Income is (At Least Somewhat) Predictable and Sustainable

I hate to break it to you, but one or two months of solid revenue isn’t any guarantee of sustained success. Anyone who’s been self-employed for several years knows that the entrepreneurial world has its seasons.

Everyone launches something in Q1, because that’s when hopes are high and our culture is interested in turning a new leaf. In Summer (at least here in the northern hemisphere), there’s the ongoing debate of launching your product or service when kids are out of school (particularly if your ideal client has a family) or waiting until things calm down in the Fall.

And then there’s always the lull of wintertime in November and December: long-time veteran entrepreneurs have set the example of pretty much taking the whole month off, while newbies squirm and plead for advice on why their sales have dropped after having a surprisingly lucrative “back to school” season.

Now, I’m the last person who’ll tell you to test your side hustle for several years before quitting your job. In fact, just writing that sentence makes my Sagittarius stomach drop. As a compromise, I’ll advise you to simply know whether it is or isn’t sustainable. Be as honest with yourself as possible, which brings me to the next tip...

Embrace the “Risk-Taker” Label

That’s you! You’re officially a risk taker. Sure, there are inherent risks in any profession and truthfully, there aren’t even many guarantees with day jobs anymore. Know anyone who has gotten laid off? Everyone takes a salaried desk job for the security, but no one really talks about how easy it is to lose your job, especially if your office has some intense corporate culture happening.

Working for yourself is risky because it’s just not as common as getting a desk job. It requires you to have difficult, sometimes taboo conversations that you’re never expected (or encouraged) to have in a corporate environment. It requires you to wear multiple hats as the marketer, bookkeeper, customer service rep, and more, while an office job divides those tasks among multiple employees. It puts the burden of revenue on you alone, instead of the big wigs and higher-ups.

Before I freak you out and convince you NOT to follow your dream, let’s flip this on its head:

Being a risk taker can be a good thing.

You’re setting an example for your kids and family that life isn’t about paying bills and then dying (despite what the memes say).

You’re actually contributing to causes like social justice, equality, and environmental change that are often easily swept under the rug behind meaningless mission statements at a typical corporate job.

If you’re a woman or a BIPOC (Black, Indigenous, or Person of Color) you’re a living, breathing example of dismantling generations of statistical evidence that “someone like you” won’t make it as an entrepreneur.

Be proud of yourself, you risk taker, you!

But first (and lastly) ...

Set Up a Financial Back-up Plan

This probably should have been first on the list, but I’ll be honest with you. Most people I know and work with who are entrepreneurs didn’t have a generous amount of savings before they took their leap of faith from their job and took their side hustle full-time. And in today’s economy, with every generation it’s getting harder and harder to save money without living a stripped down, minimalist (and let’s face it, miserable) lifestyle.

In an ideal world, you’d have enough money to sustain you for at least 6 months. You’d have cash in a high-yield savings account in whatever amount makes it so that you can keep living your life, make zero income for six whole months, and still be okay.

I don’t know about you, but I don’t know anyone who has that kind of money stashed away. Or maybe I do, but he’s the biggest stingy, penny-pinching jerk I’ve ever known and the amount of sacrifice he’s had to make to save that money is definitely showing in his face, personality, and relationships.

Let’s say you’re not the jerk face I’m thinking about. What are your options?

There are other ways to have a financial back-up plan, other than cold hard cash in the bank. For example:

Maybe you’ve got a supportive boss at your day job, and they’ve already wished you well and told you that your position is open if you ever need to come back. Yay! That’ll work.

Is going back to your job hard NO for you? What about getting a part-time job that you love, somewhere else? The world is a lot more open to remote work, post-pandemic. Try transferring to a job that will take some of the financial stress off your shoulders but still leave you with time and creativity left to build your dream business.

How about a family member who’s willing to sponsor or help you out, temporarily? You’d be surprised how supportive you quietest family members are of your dreams. I’ve even had relatives offer interest-free business loans, no question as asked (and yes, I took them up on it!) Have those scary conversations and find out.

Are you willing to sell your stuff? I’m not saying you have to clean house right now, but it would be handy (and reassuring) to know the value of the things you would sell if it ever came down to it.

There you have it! Some quick advice for when you're ready to take your side hustle full-time.

Which one of these surprised you the most? Was there something I missed, that you think should be at the top of the list? Feel free to comment below!

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