18 Experts Weigh In: “Before You Quit Your Job for Entrepreneurship…”

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If you want to turn your side hustle into a full-time business, you’re going to have to put in a lot of work. But many of us get stuck on the details and I’ve seen people fail because of the overwhelm of it all.

In fact, I started this blog because I know how personally challenging it was to find all the information I needed.

I knew I needed to learn A LOT, about business, insurance, finance, business models, etc. but I just didn’t know WHAT to learn.

Sounds confusing, right? It was.

That’s why I wanted to reach out to some folks who are a few steps ahead of you and I, to get their advice on what they think you should focus on if you’re planning to quit your job in the next 12 months.

These are people who have been there, experienced the hard times of entrepreneurship, and came out on the other side.

So I asked them:

What is the number 1 tip you have for people who are planning to quit their job in the next year to take their side hustle full-time?

Here is what they had to say:

nick loper

Nick Loper


Making the leap from employed to self-employed is an awesome — and scary — jump.

To make that leap a little less stressful, aim to build your side hustle income to the point where it consistently covers your monthly expenses, and you have several months worth of cash savings as a buffer.

Remember, you don’t necessarily need to replace your old day job salary right out of the gate, but you’ll breathe easier knowing your business has a proven track record. Plus, with an extra 40-50 hours a week to dedicate to it, I imagine it’ll only go up from there!

chris guillebeau

Chris Guillebeau


Don’t quit until you can safely project an income that’s at least 2/3rds of what you make in your job. Also, ask yourself if you could make more money if you had more time to spend on the hustle.

If yes, that’s a good sign.

By the way, if you’re single and under 25, this rule doesn’t apply. The stakes are much lower at that point in life, and even in the worst-case scenario, you could always rebound later.

So if your job sucks, no need to wait till next year—you might as well quit right now.

Rosemarie Groner


An easy way to make the transition to working for yourself is to reduce your personal spending as low as possible in the short time for a few months before you transition. This doesn’t have to be permanent (and shouldn’t be), but it does a few things for you…

  • it lets you see how much money you really need to live on
  • gives you an immediate boost to your emergency fund
  • and eliminates any distractions for your first few months so you can focus on increasing your income form self employment.

We did this- we lived for about 3 months on a $400/month grocery budget, switched from paper towels to cloth, cancelled cable, Hulu, and Netflix and never ate out. It motivated me to make this work, and gave me peace of mind while I was still figuring it out.

In the end, it was a super short sacrifice and my income is about 5x what it could have been in my traditional job working for someone else. It was completely worth the short term sacrifice.

Jason Zook


After you’ve created structure and a schedule for yourself, start working on goals for your new business. Through trial and error, I’ve found that creating three sets of goals works really well for me (and people I consult with). The sets of goals are daily, weekly, and monthly. Goal setting can feel uncomfortable and awkward at first, but like everything else, it gets better with practice.

Starting your next business while working a 9-5 job isn’t easy, but it’s absolutely doable. Put these steps in place and you’ll not only be working for yourself in no time, but you’ll also look forward to your work.

justin jackson

Justin Jackson


I’m seeing a lot of folks quitting their jobs and expecting to make $100k+ their first year. It took me years and years of working on my side-hustle before I went full-time. Bootstrapping is a long journey; you have to give it time!

You also can’t pay too much attention to other people’s results. Success has many factors. Your results will vary. Stay focused on your customers, their struggles, and your response to those needs.

Steve Chou


My #1 tip is to make sure that you have enough money in the bank to provide plenty of runway for your side hustle.

The worst thing that you can possibly do is make business decisions based on the money.  So make sure you have enough saved up and purchase the right tools that will allow you to succeed.

preston lee

Preston Lee


If you’re planning to quit your job next year, my number one tip is to have enough runway to keep you afloat for the first 6 months (at least). It’s not a super-sexy answer, but here’s why: because I care that you succeed long-term.

I don’t want you to quit your job, start building a business, and then give up because you run out of money and have to take a mediocre job in order to put food on the table.

If you have a decent runway, the pressure is off. At least, the bad kind of pressure. The pressure that causes you to make bad decisions. When you’re desperate for cash in the door, you’ll make bad decisions—maybe you’ll get too salesy with your audience, or you’ll cut our rates in half, or you’ll take jobs with clients you really never wanted in the first place.

But if you have a buffer, a runway, a safety net of sorts, you can build a business that will support you long-term. One built on integrity and passion. One built to last for years to come.

And that’s what I want for you. So while the siren call of quitting your job does seem awfully alluring, it may be worth waiting and saving for 3 more months to ensure your new venture can support you long into the future.

natalie sisson

Natalie Sisson


I’d say from experience, my biggest piece of advice is to go all in.

Obviously if you’re quitting your job it’s likely to pursue your side-hustle full time -which now means it’s a real business, and you have to treat it that way. So why not go all in?

Master your craft, hire people to help you and don’t be afraid of not having enough income to afford a team and the right tools and foundations. If what you’re doing is valuable, all this will pay for itself as your customers and clients recognize this, and step up to be lifelong supporters of your work.

Ryan Robinson


My advice for anyone wanting to quit their day job and focus on growing their side hustle full-time, is to make sure you’re already bringing in as much (or more) side income as you’re getting from your regular gig before putting in your notice and making the leap.

Getting your finances right is incredibly important, and sure you can offset the income requirement a bit by planning to fund part of your lifestyle from savings for up to six months or a year, but that’s risky. And I hate risk.

I’ve made the mistake of quitting my job too soon in the past to focus on a startup, and that landed me living back with my parents for six months when the major contract we were relying on fell through. It took time to get a job that could help me rebuild my savings and get back up to a point where I was psychologically ready handle starting another side project.

Now, it’s become my personal rule that I’m not able to quit a full-time job without already bringing in as much income from other sources—and having a full three months worth of “living” money set aside in my savings in the event of a worst-case scenario.

Take inventory of your responsibilities, always involve other stakeholders in your life in these discussions, know how much you’re already bringing in on the side and come to an agreement on what a comfortable income gap will be for you (and your family) before making the decision to leap.

caitlin pyle

Caitlin Pyle


If you’re thinking about making your side hustle your full-time gig, chances are you’ve been doing a lot of research on what you should do before you make the transition. And there’s a lot of great advice out there: have money saved up, make sure you have clients in the pipeline, have your health insurance figured out, etc. And those are all SUPER important things that every entrepreneur should do before setting up shop.

But I’ve got a different tip for you today — one you might not have thought of otherwise. Before you make any big moves, make sure your side hustle lights a fire under your butt.

That means that your side hustle better be something you are truly, deeply, 150% passionate about. It needs to be something that you can put your all into day in and day out. It has to motivate you to get up in the morning and enjoy what you do for a living.

Otherwise, what the heck is the point? Why not just keep it a side hustle and earn a few extra bucks here and there?

For example, my passion is teaching people skills so they can follow their dreams and live the life they want. It’s what drives me every single day. Sure, I sometimes have off days, but if I didn’t have a true passion for teaching, my days (and life) would be bru-tal. I wouldn’t give my business everything I had; I’d neglect to do important things; I’d become complacent and accept the status quo. I’d lose my purpose.

And that’s not a feeling you want to have… especially since our businesses are such a big part of our lives.

So before you take the leap from side hustle to full-time hustle, make sure you’re honest with yourself and gauge how passionate you are about your business. You should take that leap if and ONLY if your answer is “HECK YES! I can’t imagine my life without XYZ Business.” You’ll be thankful you were straight with yourself from the start 🙂

leslie samuel

Leslie Samuel


When you leave your job, it’s going to be very tempting to focus on the things that pay you now. Avoid that trap. Try to have a balance between that and setting up structures that will pay you into the future.

Build systems to ensure that your money continues working for you. For example, instead of focusing primarily on things like one-off consultations, focus on creating a course that you can sell over and over.

jeff sauer

Jeff Sauer


For anyone trying to take their side hustle full-time, I recommend setting a financial anchor that gives you confidence that going full-time is the right move. For example, you may choose to go full time once you hit a certain Monthly Revenue Rate (MRR) that comes close to replacing your salaried income. If you save the money from your side hustle, this confidence will come more quickly, and you will have a nice ramp to achieve your goals.

If you are providing freelancing or consulting services in your side hustle, my recommendation is to find an anchor client to replace your employee income. I’ve interviewed 50+ marketers on my Jumpstart Podcast, and the majority of those who start their own agency/consulting business started with a single anchor client on their side. Most of these anchor clients were contracts with their former employer, or an extension of their side hustle.

I define an anchor client as a single contract that replaces 75-125% of your income, in around 20 hours a week. Anchor clients give you the income and confidence to take the side hustle full-time, with enough time left over to focus on rounding out the business. This is something I teach in the Agency Jumpstart program.

It can take 12 to 24 months to make the transition from side hustle to full-time. It’s something that I have done twice in my career, and it’s been a life-changing experience.

To me, the key is smart personal financial management, and a plan for the future. It’s a lot easier to make the leap if you aren’t living paycheck to paycheck. This isn’t an overnight decision, and that’s where the 12-24 month window comes in. Work hard, hustle, save, save, save, and the decision becomes clear, whenever the time comes.

Tom Ross


It totally depends on the point you’ve reached with your side-hustle, as well as your personal situation. Quitting your job will incur varying degrees of risk.

If you’re living at home with your parents, then you can afford to take more risk, and can be more ‘all in’ with your side-hustle. If you’re supporting a family, have medical bills or are in debt etc… then it’s likely not a good idea to jump fully into your side-hustle on perhaps nothing more than a burst of inspiration you may have picked up from some online guru.

My tip would be to work out your number for what can support you at your current stage in life. If you’re 50% of the way there, working only 2-4 hours a day on your side hustle – it’s a decent bet that going full-time on it could scale and therefore support you entirely.

However, to mitigate risk, and ease the transition, it’s probably a good idea to build up some savings, and allow you a realistic a period of time to scale things up to where you need them to be.

My final tip would be don’t burn bridges at your old job. Have that as your worst case scenario insurance policy – plus parting on good terms is always the preferable scenario.

mike wilner

Mike Wilner


My advice would be to continue to grow your side hustle while you have a full-time job.

When freelancers don’t need the money and their time is constrained by time (only so much time for a side-hustle), they tend to price things based on true opportunity costs. For example, people with full-time jobs that freelance on the side think, “I already work 40+ hours per week, so if I’m going to take on this additional project, it’s going to have to be one I really like, and I’ll need to be paid well for it.”

As a result, they charge for value from the very beginning and can build a great brand. Eventually they’ll get so busy that they need to go full-time on their side hustle in order to keep up with demand, and they’ll have high income as soon as they make the leap.

On the other hand, when people plunge into full-time freelancing to early without enough deal flow, they tend to get desperate and may lower their prices or lose focus on their unique selling proposition in order to pay their bills. It can be hard to dig yourself out of this hole.

To sum up my advice, if you’re thinking about going full-time on your side-hustle, don’t stop building it until you go full-time. Keep building it while you have a solid baseline of income, and eventually it will pull you away.

Robert Farrington


If you’re planning on quitting your job and taking your side hustle full time, my number one tip would be to wait until you’re ready. That may seem odd, but just because you “can” doesn’t mean you’re “ready”.

Working from home or converting a side hustle into a full time job is different than going to a job in more ways than you’d expect.

If you’re doing it to escape a job you hate, I’d really encourage you to spend some time reflecting on if you’re ready, or you’re just escaping. You can be financially ready, but are you emotionally ready as well? It’s a big change, and one that shouldn’t be taken lightly out of disdain for your current situation.

With that being said, prepare yourself – take more vacations, ensure your finances are in order, try to build a mock routine for what life will be like when you’re on your own. This will help make the transition easier.

jason resnick

Jason Resnick


You are never going to be ready. If you feel that you are 75% of the way there, then pull the trigger and leave.

Quitting the full-time and striking out on your own is a matter of being a bit uncomfortable. If you aren’t a bit uncomfortable with your goals, where you may be headed with your business, and all the aspects of your business that aren’t in your wheelhouse, then you’d better get uncomfortable.

Otherwise, you’ll find yourself back sitting at someone else’s desk.

michelle schroeder gardner

Michelle Schroeder-Gardner


My number one tip is to build an emergency fund right now.

Emergency funds are always good to have because they can give you peace of mind if anything costly were to happen in your life, or if you were to hang a bad business month when you eventually take your side hustle full-time. Instead of building onto your stress because of whatever has happened, at least you know you can afford to pay your bills and worry about more important things, such as continuing to build your business.

ian paget

Ian Paget


Have no regrets. Taking your business from side gig to full time is scary stuff. You’re used to a stable income, but once you do take the leap you’re completely 100% on your own… Success or failure is in your hands…

Because it’s scary, we have doubts, and we may even decided we can’t do it, choosing to stick to the day job since it’s the easy, comfortable option.

But imagine yourself as an 80 year old looking back on your life. If you never made that jump you’ll always be wondering ‘what if?’. You would regret never trying, and would feel unfulfilled… It’s better to have tried and failed, rather than to have never known what it could have become.

If you screw up, what’s the worst that can happen? If you’re employable now, you’ll be employable then too. You’ve got this!

If things are going well, just go for it… you’ll never regret trying.

Final Takeaways

Thanks again to everyone who contributed their tips, make sure you check out their businesses and follow them on social media as they all have great advice past what is in this post.

Also, a lot of these tips include some variation of saving up enough money to carry you for 6-8 months while you get you’re income up once you quit.

Because it’s so important, I’ve created a calculator help you figure out how much you need to save, how long it will take, and will even give you the date you’ll have the savings account to be able to quit.

9 thoughts on “18 Experts Weigh In: “Before You Quit Your Job for Entrepreneurship…””

  1. This is such a great round up of experts and their advice is so on point! I started blogging July 2017 and hope to do it full time by the end of the year. So this info is golden to me right now. 🙂 Thanks for sharing all of their tips!

  2. I quit my 9-to-5 to work both of my businesses full-time, and it’s proven to be quite challenging due to insane timing and limited resources. I worked on both of my businesses for three years plus before taking the leap, but there was no way I could have prepared for the strange turn in life events after taking my side-hustles full-time. I got engaged and am considering adopting a sibling pair. It’s an exciting time, but it’s also extremely difficult to process for an extreme planner like myself. For now, I’m trusting the process, focusing and doing the work to ensure that my family benefits. That’s what all of this is for – my passion and their security.

  3. The first tip I’d probably share is to change your mindset and overcome your fear: the common perception is that having a “real job” is more secure than being an entrepreneur, and while it’s true on the surface, having a career has risks on their own. You can lose a high-paying job for one reason or another, for example, if you suddenly get a terminal sickness. Also, the biggest risk of “only” having a career is limiting your potential, your money will lose its value over time due to inflation, and if say, you are sick and have to quit your job, your money will decrease quickly. That’s not the case if you have an established business that can operate without you.

    Before taking the leap, the key consideration is to have at least 6-months worth of emergency fund outside your capital. Starting a business can be really tough at the first months, and by securing this fund, you can concentrate on improving the business and don’t have to worry about what to eat tomorrow. Also, plan your business properly especially about the source of capital.

  4. Also, run the numbers to see if it makes sense to roll your employer-sponsored retirement plan (e.g. 401k) into an IRA. Same goes for a pension if you are lucky enough to work somewhere offering a defined benefit plan to its employees. If nothing else, make sure you’re vested!


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