10 Tips For Leaving Your 9-5 and Adjusting to Life as an Entrepreneur

by | BiggerPockets.com

My palms were clammy, and my heart was pumping blood to my face so quickly that I was sure my cheeks were already beet red. It was a moment I’d been dreading—putting in my two weeks’ notice. I knew it would come as a shock, mostly because I really did love my job and the people I worked with. But deep down, the desire for freedom—to steer my own ship—won out. I knew that as long as that itch was there, I’d never be able to ignore it. I’d be living a lie.     

Up until that point, the most surprising thing to me was that when I told close, trusted friends that I was going to quit my job, the response wasn’t “Are you crazy!?” like I was expecting. Instead, they said, “I wish I had the courage to do that.”  

I’ll be honest. This wasn’t the first job I’ve left, but it was the best job I left.    

It has always fascinated me how people resign themselves to clocking in and out every day. They waste time and energy convincing themselves that they need the job to survive, and it becomes a self-fulfilling prophecy. Expenses inflate, and all of a sudden they’re trapped in a cycle they can’t break.  

Don’t let that happen to you. There are some key things you can do to make sure your transition to self-employment, when you decide to make it, is as seamless as possible. This will probably be the toughest part, but if you can overcome these first five steps, you’ll have the heavy lifting behind you.

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10 Tips for Leaving Your 9-5 and Adjusting to Life as an Entrepreneur

Keep your expenses low.

Easier said than done, but this is what your self-employment success will hinge on. Lower expenses mean greater flexibility. Keep the business of YOU lean, and reduce your overhead costs as much as possible. This means having a roommate (or two), not giving in to your shopping habit, and watching every discretionary expense. For some, this might be too much, and I’m not saying you can’t have little splurges every now and then. But if you are reliant on your full paycheck to fuel your lifestyle, you will never get your freedom.


Establish a parachute fund.

Trust me, decisions are so much easier when you have a stash of cash handy. Personally, I have about 3-6 months’ worth of expenses, which is lean for some, but as a single person with no dependents and a steady stream of rental/dividend income, it’s plenty. I typically reinvest most of my rental/dividend income, but I know that if I have higher than average expenses one month, I could just re-divert those dividends for a month to knock out the unexpected expense and be OK. I’ve never had to do this though—it’s definitely for a true emergency, which happens rarely.

Related: 5 Ways to Make Enough Side Money to Eventually Quit Your Job

Cultivate other opportunities and side hustles.

I left my job mainly because I had so much going on outside of work that I felt the job was getting in my way. That is the “problem” you want to have, but it’s not going to happen unless you build up other potential streams of income. I’ve invested in rental properties, built up a real estate brokerage business, done freelance writing/social media work, run my own personal finance blog, and flipped textbooks—and I’m still getting pitched different job opportunities without me even asking.  

Key to this is always hustling and being open to what comes your way. Just like with money, your hustle will have a compound effect over time. When I officially left my job, I had three more people approach me about working with them. It truly is a snowball, and every skill you add makes the snowball even bigger.


Remember that you’re not alone.

Don’t forget that everyone, at one point or another, has been where you are. Some of them wish to be where you are. You probably expect people to tell you that you’re crazy, like I expected. That’s natural, but you’ll be pleasantly surprised at how many will actually look up to you. Some may even follow in your footsteps and pull the trigger as well! In the end, you have to live for you, but remember that you’re not alone, even when it seems like you are in certain isolated moments.

This is not forever!

I’ll admit I fall victim to black-and-white thinking all the time, too. Just because you are leaving your job doesn’t mean you will never be able to get another one! If trying the whole entrepreneur thing for a while tells you that it’s not the right fit, you can always go back to traditional employment. Being an entrepreneur is NOT for everyone, so don’t feel guilty if it just isn’t right for you.

After The Talk

So, you did it. After rehearsing what you were going to say and summoning up the courage to have that dreaded, painful conversation with your employer, you officially have turned in your two weeks. They’ll go by faster than you think, as you’ll be busy tying up loose ends.

What’s next, you ask?

Here are some tips to ensure your first week as an entrepreneur is a productive one.

Continue with a routine.

When I was working, I would wake up around 6:00 a.m. I’ve found that I would wake up tired and grumpy, regardless of what time I went to bed the previous evening. The important thing here is to pay attention to how your body feels and adjust accordingly. Now I wake up a little later, usually between 7:00 and 8:00. Some entrepreneurs are probably appalled at how late that is! But I have found that by doing just that one thing, I feel better and don’t succumb to the customary afternoon haze.  

However, to make sure I was sticking to that timeline, I scheduled appointments my first week at either 8:00 or 9:00 a.m. There’s nothing like a client appointment early in the morning to light a fire under your behind. Whatever you want your routine to be, plan it out and stick to it. Everybody is going to have a different style so what works for me may not work for you.


Have a designated work area.

For me, it’s my kitchen table. I know that if I have my laptop with me at the table, it means business. No doing my work in bed or on the sofa because it’s just that more tempting to procrastinate and turn Netflix on.

If I find that I really need to pound some work out, I either go to a coffee shop or a local free co-working space. The energy there alone is often enough to pep me up even more and get me in the zone.

Related: 4 Steps for Getting Your Finances in Order BEFORE You Quit Your 9-5 to Invest

Talk to people.

This goes beyond your first week (as should all the steps, really), but set up meetings with people ahead of time. Maybe it’s an acquaintance that you’ve been meaning to catch up with but haven’t found the time to. Or perhaps it’s someone new you met at a networking event. You completely control your own schedule now—so fill it!

I can’t highlight this point enough. My network has grown exponentially because I take the time to sit down and get to know people one-on-one; in fact, I prefer it this way! You can really get to know someone, and as an entrepreneur, you can truly never know too many people.

It’s okay to reward yourself with food/coffee.

This may not apply to you (boy, do I feel sad for you if that’s the case), but I love food. I don’t drag my feet on much, but if I find that I need to work on a project that I just don’t really feel all that excited about, I head to Bruegger’s Bagels. Feel free to go wherever you want. In my city, there are a few spots that are a Bruegger’s and Caribou Coffee combined. I know—heaven, right!?

You have to tempt the little kid inside of you sometimes, and that’s totally okay. As soon as I’m on my way to Bruegger’s/Caribou, I find that I look forward to working on whatever it is that I need to work on. It’s like magic!


Set up a to-do list or goal checklist.

My previous employer turned me onto a nifty Google Chrome extension called Momentum, which makes opening a new tab a reminder of what your main priority is for the day, along with a pretty picture and a to-do list on the sidebar. And I know you (like me) open a lot of tabs. It allows you to check things off, prioritize and be inspired with a little quote and a picture, all in one minimalist little dashboard.

It doesn’t matter how you do it, but having a list of what you want to accomplish for the week is super helpful. That way, if you find that you have a moment where you’re not working on anything productive, you can re-focus your mind just by referencing your to-do list. Aim to have everything checked off by the end of the week!

Your Future is Bright

Leaving your 9-5 (I’m personally not a big fan of the word “quitting”) is difficult, regardless of the individual circumstances surrounding your decision. Growing up, getting a corporate job was just what was expected. I am so glad that I’ve learned that being entrepreneurial and going my own way is not “weird”—frankly, it’s darn courageous. I hope this article helps you make the leap when you’re ready. This is where the fun really begins!

(If you liked this article, be on the lookout for a follow up from me on how I’m building up my real estate business! Even if you’re not a broker, it should give you some business insights that are applicable to any industry.)

We’re republishing this article to help out our newer readers.

Have you left your day job or are you thinking about taking the leap?

Let me know about your experiences and any tips you might have for others in the comments section below!

About Author

Tiffany Alexy

Tiffany Alexy is the Broker/Owner of Alexy Realty Group, a boutique real estate firm located in the Raleigh-Durham, NC metro area. She actively invests in her own buy and hold projects. With several financial certifications under her belt, Tiffany specializes in helping individuals understand how real estate can fit into their investment portfolio. In her spare time, Tiffany loves to ride horses and travel.


  1. Mike McKinzie

    Great article Cyndi. My father would disagree with you about what time to get up. When we both owned a couple of Real Estate Franchises, we could get in 18 holes of golf, go home and shower and be in the office by 9:00 AM. I quit the entrepreneurial world in 1999 and joined the Corporate World and I aged 20 years in 10 years. Talk about the hamster on the wheel!! By 2010, due to circumstances, I quit the Corporate World. Since then I have purchased 15 more rental properties. I don’t think I could make it in the Corporate World, all I am doing is making someone else huge profits!

  2. Trent Honea


    I hope you find not working as rewarding as you hope it will be. I am working toward that day myself through property investing. I am also beginning to explore writing as a passive income stream.

    I don’t find writing difficult as I have seen many say, but I don’t have “the marketing gene” and am trying to learn that aspect.

    • Tiffany Alexy

      Trent, thanks for reading! It’s definitely all about the passive income. I’m definitely not at the point where I am quitting work altogether though – it’s just a shift into what kind of work I’m doing. I am one of those people that will probably never stop working… the key is to find projects that you are passionate about. Then it isn’t really work!

  3. james russell

    more and more often i hear about, “quit your job, for a better future.” obviously this cant be done lightly, but its nice to hear success stories from real people that have actually done it and are happy. thanks for the post. im inspired

  4. Tiffany,
    Wonderful article and thanks for the tip about Momentum. I’ll check it out. You are the embodiment of what Earl Nightingale warned about so many years ago – not ‘conforming’ and creating your life as you want. I am looking forward to learning more about your success and enjoying more conversations over coffee.

    • Tiffany Alexy

      Thanks Tommy! Definitely… learning about non-conformism in high school was life-changing for me. Ultimately what drives me is that I want my work to fit my lifestyle – not my lifestyle to fit my work, you know? Real estate is great at helping me do just that!

  5. Grant Fosheim

    This article is very applicable as I put in my two weeks at the end of last month. I know that sweaty palm feeling! I had a 2-3 year “to-do/goals list” building in my head, on paper and anywhere I stored any sort of notes. I am now on my second week of the entrepreneur lifestyle and I wake up at 6:30, same time as always, hit the gym (that was lacking before), put out fires in the morning then network and work on my goals sheet in the afternoon/evening. So far so good! Thanks for the awesome tips!

    • Tiffany Alexy

      Thank you for reading Zoran! As far as cutting down on expenses, I think first that assumes you are tracking your expenses — right? It doesn’t really matter where, it can be a notepad, Excel, Mint, Personal Capital.. but the important thing is you are tracking your expenses to the penny. That is the only way to know with any sort of accuracy where your money is going.

      Next, I would look at the categories and rank them in the order of how much joy they give you. Sounds weird, but I am a fan of spending money on what I value, and skimping on what I don’t. For instance, my restaurant category is pretty high, but I spend $0 on a gym (I go running at the lake). I get massages about 1x a month or so, but my clothes budget is very low as well (I go thrifting.. and yes you can still find good stuff, you just have to look!)

      I hope that helps! Spend where you value, cut where you don’t.

  6. Rick Grubbs

    I haven’t had a “real job” in over 20 years and never looked back and wondered if I did the right thing. REI has allowed me to do Christian ministry full time while raising 12 kids. God is good.

    Thanks for these reminders!

  7. Matthew Chauvin

    Thanks Tiffany!

    I am in the process of doing just that, however a 2-weeks notice doesn’t cut it where I am, more like 2-3 months. Regardless, the things I am putting into place you have touched on. This article reaffirms my convictions and lets me know I am on the right path.

    I, too, am surprised that most people are very encouraging about my decision. I do have one person who is playing devil’s advocate, and I think that attitude is the most beneficial. They cause me to dig deeper into my thought process and really be much more careful with my planning.

    Like you, my job is getting in the way of my side hustles, one of which being real estate. So, a huge thanks to BiggerPockets for being here! I have and continue to learn an incredible amount from this community.

    Great article Tiffany! Thank you!

  8. Gregory Brown

    Tiffany, great article! I left the corporate world about nine months ago. I had only been married three months and had, what I felt, more responsibility then when I was single. I remember the day, I had landed a big consulting contract with a real estate company. I told my wife I wanted to “quit” my day job and work my business full time. I have not looked back since. Owning my business full time and solely has been a hard yet rewarding task. I found your list informative and inspiring. Entrepreneurialism is my life, my passion, my biggest dream. I too would be living a lie if I had not made the jump.

  9. I really needed to read this article this morning.. I will be walking from my “comfortably uncomfortable job” as I like to call it, as a Police Officer to explore the world of becoming a business owner, here in the coming month and a half. I’ve set a hard date on which I will exit and while it’s exciting it’s also equally scary!

    Thank you for you’re tips Tiffany, much appreciated.


  10. Linda Summer


    I’m with all of the positive feedback above. I immediately downloaded the Momentum app so that I can have my to do list on all my new tabs because you are right, I open a new tab so many times per day. I agree with Fredrik Eklund that all my real resistance is myself. I have been self employed for 20 years now and would not go back to a 9-5. I moved in 1996 and had a hard time finding a 9-5 job so I started taking in ironing for some income and quickly got into cleaning houses. I heard an ad on the radio one day for massage school starting new classes so I got signed up before I changed my mind. I have been a massage therapist for the last 13 years and for many years I kept up my cleaning business simultaneously. I slowly phased out my residentials and just let my last business go in December. I have been a wanna be investor for so many years and have done a couple of wholesale deals, been to classes (beware of the overpriced) and local REIAs. I have hooked up with another successful investor who has hired me as his project manager for his flips. I am finally starting to build confidence and get some hands on education (the best). I am on track to finally wipe out my credit card debt this year and my goal is to do at least one flip on my own this year. My goal is to have enough rentals for passive income for my retirement in order to spend time with my grand children and contribute my time to any other causes I choose in the future.

    Thanks for the article and the practical tips, I’m sure Momentum will be a huge help keeping me focused on my to do list and goals. Looking forward to seeing more from you in the future.

    • Tiffany Alexy

      Thank you so much Linda! It’s great to hear your success story and how you made self employment work for you. The heart of is really the big “why” and it seems like you have it… time with your grandchildren. That is an amazing reason for anyone to pursue their own ventures versus getting stuck in the 9-5 grind: time. More important than money, IMO. Good for you for keeping it going! All the best to you!

  11. vicki gleitz

    This is awesome, Tiffany! My husband and I have recently sold our auto repair shop and are in the also scary, but super exciting, business of retirement with a few “side hustles.” We were getting a trifle lacksadassical in our day to day “pursuit of relaxation” and many of your tips inspired me to make a few tweaks.

  12. Great article! I think that the hardest part of doing work on your own is your career trajectory. I’ve found it not only helpful, but sometimes fun to continue to go to workshops and utilize educational materials to help keep me moving.

  13. Christopher Coleman

    Thank you for the help, Tiffany. This is an amazing article!

    I’m currently a teacher and really don’t see myself continuing to teach. I know I’m on a never-ending cycle of being unappreciated, grossly underpaid, and spending very little time with my family while building very little financial wealth. With that being said, there’s very little in my savings and I plan on saving as much as I can for the last 4 months remaining in the school year but it will be nowhere near your recommended savings amount. Do you have any suggestions as to how I can raise the capital to become a REI?

  14. Tiffany Alexy

    Hey Christopher! Thanks for the kind words! I totally understand. Depending on what kind of subject you teach, maybe there are tutoring opportunities available to earn extra money? I know SAT/ACT tutors and such can each some pretty decent money. I know that would take you away from your family even more in the short term, though. Other than that, it’s just a waiting game… maybe check your expenses again and see if there’s anything you can reduce?

    I don’t know if you read the Mr. Money Mustache blog, but there is a forum poster there who is a real estate investor and has done it on a teacher’s salary (he and his wife are both teachers in the Las Vegas area I believe). They have something like 30 properties I think and have now retired to do some traveling, and I think they’ve barely turned 30. You might be able to get some insight from his posts! His username is arebelspy.

    I hope that helps!

  15. Wendy Brown

    Nice post I’m there now. I hate my job I’ve stuck with it for four years, hoping things would get better, but it doesn’t. Good thing for me I got hurt on the job and I now have the opportunity to start working for myself.
    I have learned to live off of less the last four years, so living off of workers compensation pay is easy. I’ve had my mortgage modify to a lower interest rate down to 3%, which brought down my monthly payment. I’m doing work from home as a product support for Turbo Tax, and can pick up other clients as needed. I’ve also started my real estate whole selling business. I’m now trying to learn every thing possible about the business. I’ve taken a few steps by setting up my e-mail site and Google voice number, and business cards. I’ve join Bigger Pockets, I’ve read so many articles, and sat thru many of webinar and watch videos. I receive leads every day thru my e-mail account. I feel that I’m just about ready to pull the trigger. I make it a point to get up early and work out, and to keep a routine going so I won’t get lazy. It’s scary but I’m already happier been away from that job. I’ve just given it to god and letting him drive.

    • Tiffany Alexy

      Wendy, so great to hear your story, thank you for sharing! I agree it can be terrifying at times, but it all works out in the end, and usually if you’re resourceful things just have a way of working out. Sounds like you are! Hope things continue to go well for you! I admire your ability to do early morning workouts… I am terrible at it! My business partner has a 5am routine though and it amazes me… kudos to you! That is not easy.

  16. Cornelius Charles

    Great Post Tiffany. I really enjoyed it. As a new investor, I know that one of my weaknesses is growing my network. I think this is the hardest part about trying to invest part time is trying to find time during the week to meet with people (other than REIAs). I need to make this a priority and try to start meeting with people on the weekends.

    Thanks again.

  17. Naren Gunasekera

    Great article. I’m a fan of waking up early though 🙂 5am and I can get a lot done. I started in the corporate world, switched to my own company in the tourism field and now I’m back in the corporate world. I learned a lot as an entrepreneur and my aim is to get back into that through real estate. Thanks for sharing these tips!

  18. Alexis Mobley

    Tiffany, I feel like a lot of what you said are things I am concerned about when it comes to making real estate investing a full-time thing. I have not done a single deal but I know I would like to get to the point where I do not need to exchange hours for a paycheck. Maybe in 10 years or so but we all start somewhere!

  19. Thank you so much for sharing. Very inspirational. I am currently studying for the real estate agent exam at the same time I am working a “long hour” job, which I’m probably going to put on hold for a week or so closer to the test to really focus. Getting a lot of different streams of passive income is key to it. Thanks again.

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