How To Avoid Crawling Back To Your Boss After You Leave The 9-to-5 Grind

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It’s what we’re all chasing after—that moment when you’re officially the head of your own profitable company, and you never have to go to that stupid office job again. But will you be ready to finally make that move? Do you have the tools and the mindset to overcome the common, but often unexpected pitfalls that will send you crawling back to your old boss?

Don’t worry, we’ve got you covered.

Say you’ve spent the last couple of months working on your side hustle, you’ve made the necessary plans, and you’re ready to quit your job. In short, you’re feeling that you’re finally ready to abandon the 9-to-5 rat race and become an entrepreneur, full time.

Or maybe you’re only just getting started and have zero idea what life is like in the undiscovered country of being a startup founder. (If that’s you, feel free to check out the other awesome stuff we’ve got going on at Foundr.)

It’s perfectly legitimate to have some fear about the transition to entrepreneurial life. As ready as you might think you are, there truly are some things that almost everyone struggles with, even the geniuses among us.

To help you with that transition, and to know just what to expect on the other side, we’ve pulled together the five most common struggles people face when they ditch the 9-to-5, along with the tools you need to overcome them.

The New Entrepreneur’s Rut, and How to Avoid It

Something that often trips up many entrepreneurs when they leave the 9-to-5 for greener pastures is that their productivity takes a nosedive.

Don’t feel bad, you can’t help it. For one thing, your brain is naturally not that good at planning. It turns out that we all tend to struggle when it comes to estimating how much time and resources are needed to complete a project.

When it comes to making a plan, we have a tendency to forget that things can go wrong, and we make plans based around the assumption that everything is going to go swimmingly.

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So as much as you might hope that once in your home office you’re going to put your head down and start working like a madman, it’s more likely that you’ll find yourself standing in the kitchen trying to figure out what blend of tea or coffee you want to start your day off with, because everything needs to be “just right.”

Don’t worry though, it happens to the best of us. Our very own CEO and founder Nathan Chan found that when he changed careers and started working on Foundr full time, he actually got less done than when he was still working on Foundr as a side hustle.

That’s a common phenomenon witnessed by none other than Jessica Livingston in her time mentoring hundreds of entrepreneurs at the helm of famed startup incubator Y-Combinator.

Fortunately, the solution to this particular stumbling block is relatively easy.

Solution: Manage your expectations and harness your habit fields.

If you put pressure on yourself to get everything right and be a superstar right out of the gate, honey, you’ve got a storm coming. Go easy on yourself in your first couple of weeks as a full-time entrepreneur. Experiment with your schedule and find a system that works for you first instead of going in with the mindset that you need to hit the ground running.

One way to make this easier is to learn how to manipulate your habit fields by optimizing your work environment. The same way memories can become associated with certain items, habits and mindsets can become associated with certain rooms and objects.

That’s why you’ll often find it difficult to work in your bedroom as opposed to the office. You need to give your brain the right context to switch gears and go from home mode to work mode.

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If you don’t happen to have a space at home that you can turn into a designated workspace, try setting up rituals or habits to help you get into “work mode.” Something I like to do is make sure I still put on my work clothes, and head out to grab a coffee from the local cafe, so when I come back home I’m in the right headspace to get things done.

Worried about ditching the security of your 9-to-5 job to branch out into the exciting world of entrepreneurship? We understand and we got you covered!

Click Here To Get Our FREE “Ultimate Step-By-Step Guide To Leaving Your 9-5 Job!”

What if Living Your Dream Makes You Miserable?

One thing to get used to very quickly when it comes to being an entrepreneur, is that being uncomfortable is your new comfort zone. The very nature of entrepreneurship means that you’re challenging the status quo in one way or another, and always pushing the envelope.

The 9-to-5 life can be such a drag, that it’s easy to overlook what we’re giving up when we leave it behind. Things like a guaranteed wage, insurance, and guidance whenever you need it go out the window once we stop being someone’s employee.

When you’re the founder of your own startup, you’re suddenly responsible for everything. It’s up to you, and no one else, to constantly be driving the ship forward and to make sure that everything is running on time and things are getting done.

It’s no wonder that entrepreneurs are more likely to burn out in comparison to everyone else. All that stress and pressure is enough to drive anyone insane.

When we spoke with Brad Feld, co-founder of Techstars, he openly talked about hard it is to be an entrepreneur and his battles with depression.

Leave the 9-to-5- Brad Feld

Now don’t start freaking out on me; leaving your 9-to-5 does not mean you’re dooming yourself to a life of stress and anxiety. Thankfully, there are ways you can overcome that feeling of discomfort. And if you’re freaking out already, this is a good a time as any to start working on it!

Solution: New entrepreneurs should learn the art of mindfulness.

To prepare yourself for the rollercoaster ride that is entrepreneurship, we recommend you start practicing mindfulness meditation, the practice of routinely observing how you’re feeling and what you’re thinking about.

This practice is how Arianna Huffington manages the stress of being one of the digital age’s greatest media moguls, and running multiple, multimillion-dollar companies.

Multiple studies have shown that practicing mindfulness literally changes your brain, improving your cognitive functions, learning, memory, and making you much more emotionally adjusted.

Leave the 9-to-5-Brain

It’s no wonder so many successful people recommend meditation as a way to help you deal with stress. Others keep journals, or seek relaxation and wellbeing through exercise. These are all healthy habits that can do wonders in helping you roll with the punches that life, and not just entrepreneurship, throws your way.

Another great place to start to mastering mindfulness would be Foundr Magazine’s special issue devoted entirely to mindfulness.

Leave the 9-to-5-The Mindfull Issue-Deepak Chopra

You can check out our exclusive interviews with the likes of Deepak Chopra, Andy Puddicombe, and more on how you can master mindfulness.

Parents (Among Others) Just Don’t Understand

This is a difficult experience for new entrepreneurs when they first start working on their businesses full time. The fact of the matter is that not everyone is going to understand why you’re leaving your stable job in favor of pursuing the admittedly risky world of entrepreneurship.

“Look they’re hiring!” – Your well-meaning, if not annoying, friends and family

In order to make it as an entrepreneur, you’re going to need some pretty thick skin, along with a healthy dose of self-confidence and ego to get you through.

As well-meaning as your close friends and loved ones can be with their criticism, it can be hard to not take it personally when they suggest you give up. After all, you’ve put in so much time and energy into building your business to what it is today, it can be painful to have the people closest to you suggest that you should do something else.

Not only does it feel like a vote of no confidence, but it can also be damaging to your sense of self worth at a time when you need to be validated the most.

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Solution: Build a network of entrepreneurial support

Let’s be honest, entrepreneurs are a bit of a weird bunch, and not everyone is going to necessarily “get” why you’re doing what you’re doing. This is why it’s critical that you seek out other entrepreneurs who can understand what you’re going through, and can provide that type of support you need.

Even if it’s chatting with one another over drinks and talking about about how crappy it is trying to pitch to investors, you need to have people you can commiserate with. Humans are, by our very nature, social creatures, so you can’t just fool yourself into thinking that you don’t need the support you can only get from other people.

But this doesn’t have to be a black-and-white choice between hanging out with your new entrepreneurial buddies, and spending time with your oldest friends and family.

Leave the 9-to-5- Happy business people using laptop in meeting

“Hah! Look at these normies!” – What your well-meaning friends and family think goes on when you’re not around.

Before you officially leave the 9-to-5, make sure to let your friends and family know what they can expect. You don’t need to hold a townhall-style meeting and lay down the law of “I’m never going to see any of you ever again unless it’s the holidays, and even then probably not.”

But do let them know that even though you’re not punching a clock, you still have a job and you are indeed working. Especially if you have a partner or children, it’s critical that they understand working from home doesn’t translate into having all the free time in the world.

It can be a tough conversation, but one well worth having.

Welcome to a Life of High-Stakes Decisions

One thing we often take for granted when it comes to working for someone else is that there is a certain degree of safety when it comes to making decisions. If you make a wrong decision, you might get a talking to from your boss or, worst-case scenario, you might get fired.

Generally speaking, the decisions you make as an employee tend to impact you, your department, and those working in your close vicinity. Unless you really screw up, your work decisions won’t be the be-all-end-all for the company. You’re one player on a team.

As an entrepreneur, though, you suddenly have a lot more responsibility on your shoulders. The decisions you make as the founder of a business carry a lot more weight. The choices you make have potentially long-term effects on the success, and even survival, of your business.

If need be, go over the solutions we laid out earlier in the article. It’s okay, I’ll wait.

When you leave the 9-to-5 and dive into the world of entrepreneurship, you’ll be surprised at the sheer number of decisions you have to make every single day. From small daily decisions like what you’re going to be working on that day, to big decisions like whether to bootstrap or seek funding.

All of these decisions, large and small, add up over time. You may even get to the point where you struggle to assess the options in front of you and end up making a choice that you’ll ultimately regret.

This is one reason some of the most successful people in the history—like Mark Zuckerberg, Steve Jobs, and Albert Einstein—choose to wear the same thing every day. One less decision to make is one less thing to worry about, and that means you can save up your mental acuity for things that actually matter.

Solution: Conserve Your Attention for the Most Important Decisions

This doesn’t mean you need to throw out your entire wardrobe and buy a hundred turtlenecks, but you should start thinking of ways you can reduce the number of decisions you make in your everyday life.

You can start off by creating more set routines and processes. For example, create a solid morning routine to follow. This way, as soon as you wake up you know exactly what to do and you don’t need to waste any time thinking about what to do next.

Another approach is to start looking for help. This is generally when assistants, whether virtual or in person, can be a great help. While you might not be ready to make a hire just yet, start thinking about people you can bring on board to help you reduce the number of decisions you have to make, so you can focus on the bigger picture instead.

Worried about ditching the security of your 9-to-5 job to branch out into the exciting world of entrepreneurship? We understand and we got you covered!

Click Here To Get Our FREE “Ultimate Step-By-Step Guide To Leaving Your 9-5 Job!”

‘Why Am I Doing This Again?’

Entrepreneurship is difficult, and there’s no getting around that.

Whether it’s an unexpected mishap, a lack of support, or even just burning yourself out, there will be a point when you’ll feel like you’re at the end of your rope and you can’t keep moving on. Some of you reading this might be feeling this way right now.

This isn’t to scare you away from making the jump to becoming a full-time entrepreneur. After all, you’ll struggle to find something that is quite so fulfilling and can give you as much control over your own destiny as entrepreneurship can.

The crazy thing is, in the entire history of Foundr, every entrepreneur that we’ve interviewed, featured, and spoken with all have their own story of when they felt like they couldn’t go on. It’s a universal feeling that, thankfully, has a universal solution.

Solution: Get back to basics—focus on your “why.”

Anytime anyone asks me if they should leave the 9-to-5 to pursue a business idea, I always ask them, “Why do you want to be an entrepreneur?”

Besides the fact that I like being that annoying guy who answers a question with a question, it is a valid response. If you’re going to dive into the world of entrepreneurship, and the rollercoaster of emotions that come with it, you’re going to need a very good reason for doing so.

Are you doing this to make money? Is it because you want to become more independent? Do you just like the idea of creating a business?

Whatever your personal reason, you’re going to need to do everything you can to hang on tight to it. When the going gets tough and you ask yourself what the point of it all is, you can look back to your “why” and keep on going.

Something else to keep in mind for when you leave the 9-to-5 is to make sure you keep yourself inspired. Your motivation, like your decision-making ability, is a finite resource, so you have to make sure that you top it up whenever you can.

Don’t just slap up a couple of “Hang In There!” cat posters on your walls—actually deliberately do things that inspire you.

One great place to start would be to check out the Foundr podcast and listen to what your entrepreneurial role models have to say about their own journeys and how they got to where they are today.

Give yourself a break and just sit on the couch and read a book, or watch a movie that you know will get you into the right mindset. Don’t consider it slacking off, but more like you’re feeding the fire that is your inspiration.

Personally, I always watch Paul Blart: Mall Cop whenever I need to find inspiration.

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I challenge you to find something more inspirational than the image of Kevin James on a segway.

Worried about ditching the security of your 9-to-5 job to branch out into the exciting world of entrepreneurship? We understand and we got you covered!

Click Here To Get Our FREE “Ultimate Step-By-Step Guide To Leaving Your 9-5 Job!”


At the end of the day, nothing can ever really prepare you for the journey that is entrepreneurship. Everyone’s journey is unique, with its own twists and turns. But if you look closely, you can spot a couple of common hurdles to look out for.

Now that you’re aware of what to look out for, I hope you’re feeling a little more prepared to leave that 9-to-5 and take that plunge into entrepreneurship.

It’s filled with risk, and it’s rarely easy, but since you’ve read this far, I know you have what it takes to go after your dream.

What stage are you at on your own journey? And what’s your biggest concern about ditching the 9-to-5 and becoming a full-time entrepreneur? Let us know in the comments below!

  • Simon Nung

    I love the use of gifs and stickman picture… Its definitely an ice breaker. I might have to do the same with my emails when writing to emails.

    • Jonathan Chan

      I always enjoy being a little bit more unconventional with the images I use in articles, just helps in grabbing people’s attention and gives me the chance to make my writing a bit more personal.

  • Maya

    Definitely the bi-weekly paychecks. Oh sweet “security”. LOL

    • Jonathan Chan

      You never know what you’ve got til it’s gone haha

  • Mercy F. Espin

    One of my biggest fears is “not being able to face my financials responsabilities after quiting my job, since it would take a few months (with good luck) to start making money from my business…

  • BH

    I’ve been at my business for a few years and STILL struggle with EVERY SINGLE THING you said in this article. Thank you for letting me know it’s normal. And it’s normal even when you’re still struggling to grow, no matter how long you’ve been at it. This makes me feel like I’m normal.

    • Jonathan Chan

      Great to hear you enjoyed the article BH, and trust me when I say that you are definitely not the only entrepreneur out there going through this.

  • Nicolas Ganea

    I talked about this in a video and linked you guys! So true! going through this myself! So used to working 14 hours to 18 a day and then finally became self employed I got all that free time I wanted. I finally getting back a swing of things. It really takes time!

    • Jonathan Chan

      Thanks for linking back to us Nicholas! It definitely does take time to get back into the swing of things, but when you do there’s no stopping!

      • Nicolas Ganea


    • BH

      I don’t know anything about free time. I work 14-15 hours a day every weekday and usually 4 hours a day on the weekends. How do you have so much free time?

      • Nicolas Ganea

        BH I pick and choose what to do with time. What makes me money and what makes me move forward. One of my business allows me that I work one day (sundays) charge $800 per client for a monthly service and the rest of the week I get to meet people.

        Make videos, do photography for giggles events for cooking. Chill with my fiancee when she not working then with my old friend we are building a program together. I make my own roster.

        • BH

          I have two businesses, and there is a never-ending amount of work to do. I don’t have any employees yet so it’s very challenging. My VA’s help a bit, but not a lot. Any advice?

          • Nicolas Ganea

            Just the sounds of this writing tells me you don’t trust your Va to do much and you are annoyed can’t things fast as you. Am I wrong?

            First thing is you need to Accept no one will ever work as hard you in your Company because you are the brains and the person with the vision that’s why. And you should be working harder than anyone in your company.

            Second where are you spending your time at? Are you spending your time in the 10 dollars an hour 20? 100? 1000? 10,000? Hour?

            10,000 is creating systems how can you reach your vision? Etc 1000 is keeping the structure, culture in place.

            Ask yourself the question would you see employee do this or CEO or manger doing this job?

            Remember you are the top of the pyramid as you grow you have let go of things and create the Lego effect ( which is the 10,000 hour areas)

            Like example I just found another kind of audience by accident… creating Meal plans and just taking video and pictures and the money that being made will pay for the videographer and graphic designer which will pay for its self each week. Allowing more brand awareness but that’s not something I should be doing because that’s the 25 to 100 hour. I should only be doing this to create System

            What will help you a lot of reading “e myths revised ” I was guilty of all the problems were mentioned in the book.


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