Corbett Barr

Lifestyle Business Weekly

4 Ways to Leave Your Job

New readers write me weekly asking how I made the transition from corporate work to self employed.

Specifically, they want to know how it works from a financial perspective. Do you leave your day job? Do you stay full-time and just work on your own project evenings and weekends? If so, when do you finally make the leap?

There are lots of ways you can leave your job for self-employment, but most of them are variations of a handful of categories.

Here are four typical ways you can leave your job. I’d love to hear your thoughts in the comments.

  1. Keep working your current job. Build your business on the side. Leave when it can support you.

    Moonlighting. Side hustling. Evenings and weekends. Whatever you call it, this is the most “safe” bet from a financial perspective. You continue to earn a salary from your regular job while building your business.

    The financial stability is the main benefit of this approach.

    But consider the downsides: you’ll be exhausted from working so much. You won’t have much time for your side business. In fact, you might never get it off the ground. You might not have a strong motivation to bring in income from your entrepreneurial activities (because your bills are paid).

    Also, you might jeopardize your day job if your work gets sloppy due to your newfound distraction.

  2. Negotiate working less at your current job. Earn just enough to pay the bills.

    If you can swing it, this can be a great in-between option. You’ll still pay the bills, but your financial position will be tighter and might provide some needed motivation. You’ll also have more time to work on your side project.

    This is the route I went for a few months before taking the full plunge. My employer at the time was open to me working half-time and I jumped at the chance.

    The trouble is, most people will have a hard time negotiating an arrangement like this. You might also tip your employer off to the idea that you’ll be working on something else, so be careful.

    On the other hand, if you’re serious about leaving, it probably doesn’t hurt to ask.

  3. Find a new gig that pays the bills but gives you more time/freedom.

    If you really want to lower your hours so you can focus more on your new business, maybe you should look for a different job that will let you work part time.

    This might be especially good if you find a job that has low overhead and baggage outside of your working hours. Since this isn’t a career step for you, you’ll have freedom to take a job you might not otherwise.

    Better yet, you could start freelancing in the field your new business is in. That way you’ll be immersed in thinking about your new field whether you’re at your job or working on your business.

  4. Take the leap. Survive on savings.

    This is the ballsy-ist option of all.

    I first took the leap over 6 years ago. After a few months of part-time work, I decided I needed to fly without a safety net to really motivate me to make the new business work.

    In some ways, this can work, but there’s a fine line. A little too much financial security might keep you from being motivated. Not enough security might paralyze you with stress or fear.

    In the end it worked out fine for me, but there was a rough six months or so in there when I was stressed to the max and freaked out about whether it would turn out OK.

    If there’s a chance you won’t handle the stress well, you might be better off with one of the other options above.

Of course, there are a lot more factors that will weigh on your decision. If you have a spouse or family, they’ll play a big part. Consider your family and relationship dynamics as well and think about how each of these options might affect them.

Now I’d love to hear from you. Have you tried any of these options? Are you thinking about any? Are there other options I left out?

Please share in the comments!

If you haven’t stopped by my other blog Think Traffic in a while, come see what we’ve done with the new design over there. We’ve been getting rave reviews :)

Corbett Barr

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  1. Hey Corbett,

    I’ve been working on option 1, but I’m just getting started. I don’t ever have to work more than 40 hours a week and the hours are flexible, so I’ve been getting to work early so that I can leave early and have a decent amount of time to work on my side hustle in the afternoon and evening. I wish I had the savings to just take the plunge, but financial situations aren’t allowing me to do that right now.

    I just have to keep remembering what my ultimate dream is, and I figure that as long as I work as hard as I can, eventually it will work out for me. Thanks for the insights again, your writing has been an essential part of my change in mindset and realization of what I really want. So thanks!

    -Brock Taylor

    • I did option 1 for 3 years until I finally announced my engineered layoff this week.

      It has been a GREAT ride and I wasn’t tired at all working for 3-4 hours afterwork. It was exhilarating.

      If you can figure out a nice severance package, it makes leave a NO BRAINER.

      Best, Sam

  2. Jeff G

    I’m doing option #1, but I can see what you mean in #4 about needing the extra motivation!

    It’s a tough balance, because my wife really doesn’t want to deal with the stress that comes with #4, but I struggle to deal with the workload of #1… The only saving grace – I LOVE the side business, so it’s more fun than work!

  3. Luis

    I am exactly doing option 1. My job leaves me with flexible times and I can pretty much use my own schedule. I decided to wake up early and devote hours to my side business (which is not ready yet), then devote the afternoon and the evening to my “normal” job.
    The difficulty I’m experiencing is that my job interferes with my business. It is not easy to do these two things simultaneously and I don’t find myself with so much mental strength as I would have if I had only my business (that’s why I decided to shift the time I devote to it to the early morning, instead of the evening).

    Option 2 for me is undoable. Options 3 and 4 aren’t viable either due to debt, but I’d prefer these if I could choose them.

    Thanks for your great blog, Corbett


  4. Corbett:

    Nice post! Great to see it laid out like this.

    When I first started out years ago, creating my holistic career counseling practice, I started out with a messy combo of #3, #4 and #2. When I got laid off from my “transition job” after a few months, I took the leap into working full-time in my practice. But, during super slow periods, I would take side work to fill in the financial gaps.

    If there’s one wish I had, it would be that people would draw a line in the sand for themselves. I’ve seen so many would-be entrepreneurs go into unnecessary bankruptcy or financial ruin, by not leaping in soon enough to bring in extra money, when their venture isn’t.

  5. Paul

    Hey Corbett,

    I’m in Durban, South Africa and have loved this post.

    Really inspiring. I am sitting in about Option 2 with a bit of Option 1 at times due to workload. I have a real inspired business idea but it has taken me 6 months to finally pitch it to investors! I know for a fact that had I not had a job I would have been far more motivated, but then I would never have been able to support my wife and daughter the way the need. So it really does have its pros and cons. I’m in the fortunate situation that my business plan is pretty solid and is going to give me a decent return within the first 2 months, but I need to get more motivated to actually get working! And the cycle continues… I know for a fact that when I speak to my boss about my ambitions and am finally released to focus on the business full-time the productivity will explode.

    Thanks for the inspiration though. Really good stuff. I can’t think of any further options off hand. I think you’ve covered most entrepreneur’s options here.

  6. I’ve been utilizing option one for the last nine months while trying to get my blog off the ground, and my sister and I just opened an online shop as well. We’d like to open a physical location within the next year, but between my full time job and my blog, I hardly have time to keep the shop updated, let alone trying to grow the business. I’m starting to get really frustrated (and extremely sleep deprived), and I know that my performance is suffering in all areas.

    Common sense says I need to drop one of my extraneous projects and focus on my day job so that I have a steady income to pay the bills… But, I say eff that.

    I’ve been seriously considering saving up some money for a few months and then taking the plunge, but I really like the idea of option #3. I will definitely have to look into possibilities along that line.

    Thanks for the fantastic idea!

  7. Corbett

    I started option 1, 6 years ago.

    For 3 years I worked part-time in the evenings and weekends building my on-line business. After 3 years of doing that, I was ready to make the leap.

    Three years later, working full-time on my own business and I love it.

    A work friend of mine started his own property business, on the side. He worked full time but was not interested in working extra hours for extra money or building his career. He did a good day’s job and no more.

    On the side, he was saving and buying and letting out property. Within 4 years, he left work and retired! He was only 30.


  8. Dan

    Hi Corbett. I went with option 4 about 6 months ago, having saved up some money, but I’m now having to look for part time work again as I’m not quite making enough yet on my own. I would advise people not to take the plunge until they have some sort of plan for how they will make ends meet. Winging it is likely to lead to stress and financial difficulty. Having said that, it’s good to practice living frugally.

  9. Hey Corbett,

    I think I have a #5 – Rent out your Home & Downsize

    I too had a very well paid corporate job and gave it up for a more modest life in the countryside (which I am loving) – primarily to spend quality time with my kids (thinking at the time I can always go back to work later if I really have to, my network may not be as strong but it should still be there in some form) but also for the freedom this life offers.

    This was a big leap psychologically particularly as the pace of life and intellectual challenges are very different. For quite a while I felt very guilty, like I should be ‘doing’ something but after about 6 months I started to get a routine and interested in things like online stuff to have something to learn and challenge me technically.

    Financially we also had something of a safety net as we downsized considerably and rented out our old house in London rather than selling up completely. This gives us a little income and as we now live a very modest life we’re finding that it’s more than enough.

    Two years on and I’m now finding ways to be paid in location-independent ventures and hopefully shouldn’t have to return to a corporate career (not that I disliked it or anything, I just prefer having the freedom).

    • If you rent out your house, do you just rent something smaller?

      I’ve thought the same thing and moving to Hawaii where I have a paid off house. But, SF is killer awesome for entrepreneurial activities!

  10. Great to read the above 4 reactions! To me it shows there is only 1 good way to leave your job and that is the way you choose to leave your job! Even if it doesn’t turn out too well: making that decision at that time should tell you it was the right desicion to make at that particular time!

    My personal story? about 18 months ago I came up with a project which I finalized 12 months later. Since the beginning of this year is online and I’m working hard to make it a fulltime job. I tried option 2, but like you said Corbett: my employer wasn’t too keen on making an arrangement like that.

    So I went on to option 3. I found a new job, making sure I would work in shifts which now not only provides me with plenty of time to spend on 3dayz, but I also get in more money than my previous job did.

    Leaves me with wishing everybody who is about to make that big decision good luck and I’m looking forward to your next post Corbett!

  11. I’m taking option 4… Sayonara folks!
    The thing is, my current job is killing me. I realized it’s better to take the leap rather than wait for my dead-end job to devour my soul. It’s not just a matter of money in my case. I just want to do something that I really want for once.
    But the again, I’m single and have no family to think about, although I also help my parents financially.
    I guess I’m confident that if freelance writing doesn’t work out (and I will do my best to make it work), I know I tried. I will have no regrets in the future.

  12. I’m embarking on #4 as we speak (Last day at work is June 22.) Have a bit of a side hustle started but definitely not enough to live on and enough savings for about 6-9 months. :-) Should be an adventure!

    • Sarah,

      It’ll be awesome!

      I’ve talked to a couple people, now, who have left corporate America and everyone, including me, found the initial change very disorienting. Be prepared for that and try to start out with some type of schedule.


  13. Hey! I’m writing a Guide on this very topic.

    I took the Leap of Faith two months ago with 13 months savings. Took one month to do nothing and am now trying all those things “I always wanted to do”. Keeping your options completely open to what materializes for you is key. I’ve taken some part-time work that’s turned out to be amazingly fulfilling.

    One of the “other” options I discuss in my guide is retraining while at your current job if your new field is something that fits into… like, say nursing.

    Debating whether to go back a re-write with some of this info…


  14. I’m trying #1. Problem is, I’ve created a pretty comfy standard of living. If I retire, I’ll have a healthy passive income with my retirement benefits, but nowhere close to my current standard of living. I’m hoping whatever I build can at least make up the difference, maintaining my income, but radically increasing my autonomy. I’m keeping a journal of my progress on my site. My concern is that it will be far too easy to simply go do another 60-hour-a-week job after I transition, maintaining or increasing my income, but sacrificing my quality of life. But, I will resist!

  15. What about option #5? Knowing it’s time to take the leap with no safety net? ;-)

    The days alternate between gutsy ballsy gusto, and whole crap what have I done, but each si equally as motivating!

    Although as me again in 3 months and we’ll see where i’m at!

  16. To leave a job (or start anything), it is wise to always start at #1. It takes time understand a new way to make money. If it does not work out after a few months you can always keep doing your normal job. As things progress with your new endeavor you can go down the list.

    Good stuff.

  17. Thanks so much for this post! I appreciate getting that question answered. I’m doing option #1 and it’s going slow. I think it’s the only option I’m personally comfortable with but, it’s hard to tell if my small business is going to make it or flop. I’ve gotten a few freelance jobs which is great but, not enough to know if this is something I could ever support myself or family on. I’m almost fustrated by having to go to work because I feel I could do so much more on my small business if I had the time!

  18. I’m currently doing #1 (there’s a juvenile toilet joke here that I’m resisting). I think this is really the smartest way to go. It’s frustrating as hell because there’s just not enough time. You always want more… but that’s true of just about everything in life. Human nature… we always want more of something that makes us happy.

    While moving slow is frustrating, remember that it’s forward motion. This is better than no motion at all.

    It’s tempting to jump and go all in like you discuss in #4. If I didn’t have a family to take care of, I’d probably seriously consider it. Michael Santiago brings up a good point in the comments here… “It takes time to understand a new way to make money.” So true. I’ve had a couple starts and stops withe different ventures over the past couple years and I’ve learned that no matter how much planning and thought you put into your new endeavor, there’s going to be unforeseen things that get in your way. Lots of them. You really should roll up your sleeves and work at it for a while before going all in.

  19. I’m back to trying #4 again. This time I don’t want to go back to #1. For me #1 left no time to have a personal life. I thought #2 could work, and did that for a while, but I found that if you want ownership in what you are working on, it can be hard to just do the work when you want to have more say in the outcome. For me, it’s a balance between financial health and mental health (and that’s not even mentioning physical health.) After a while, whether you have a sure-fire plan or not, if you are not happy with how you are spending the majority of the hours of your day, you need to take the time to find a way to enjoy life and utilize your true talents. Just my experience.

    • There’s also the option to leave your job and go back to school full time. Actually I sometimes think of #4 as going back to school without having to pay the tuition, a kind of independent study or practical application of sorts.

  20. Corbett,

    I’m glad to read this post. I was one of the many who asked you this question via email. You were very kind to take the time to respond to me. I see that you have expanded more on what you had told me so this post is fantastic. I’m on option #1 hoping to move to 2 or straight to 4. Keep up the great work that you do man!

  21. I choose option #4. After several months of side hustle I noticed that by doing both – job and my business, I lose motivation in job, but also often am too tired for my business. Well I decided to quit, even though I’m not doing enough money to live from. But I have savings; it should enough for 6 months or so. The plan is to move to south East Asia, of course with my wife and small kid. I know, sounds crazy, but it will be definitely not boring!

  22. Go figure, I took the most ballsy. It wasn’t the smartest but it’s not something I can change now – 2.5 years later. Key is that I’m still alive :)

  23. Corbett,

    I have been working on option #1 for the past 5 years, it been good at times but have taken a toll on my family and relationship. As many of you know its hard balancing day job, new business start up and family.

    Since the start of 2012, I have started saving more and reducing my expenses, and I’m now working on option #3.

    I would love to do option #4, but private health insurance is so costly, that is the may reason I’m holding on to a day job.

  24. I must be the craziest of all. I went with a variation of #4 except with NO savings. Yep. I only had $6k if you can call that “savings” (I took a big fat check from my retirement ‘savings’). I then moved to SE Asia then went on a bunch of free adventures like zen buddhist meditation retreats.. traveling for free in Taiwan pretty much paid for by the Buddhist organization with serious crazy abundance! Those monks are techy now, and they own iPads and iPhones. Then I ran out of money in a year (or I guess you could say, in a span of 3 months after the whole hippy thing) and ‘survived’ living in the Manila slums. Not much motivation to build my biz tho since rent was only $50 and sometimes I was only making $300/mo like a local. I guess I do some pretty crazy things and make pretty crazy sacrifices.. But now I find myself stuck in a dayjob again in interim.. and I think I’m crazy enough AGAIN to quit without savings *and stalk WDS*. My freelance has not had the chance to properly get off the ground and my rent has gone up because I just bought a condo….. But my intuition is telling me I’m all in.

    • Janet, WOW! How did you latch on to the Buddhist monks?? Did you enjoy Taipei and all the lu rou fan and ou ah jian?

      I just announced my leap of faith this week and will probably stop by Taipei as well since I have a lot of friends there.

  25. I’ve done 1 for around 10 years now. Its easy if you stick to stuff that can expand to fit the time available (so blogging is perfect).

    I’ve tried 2, but no luck there.

    Really I need to do 4, but that takes some balls.

  26. Hey Corbett —

    I did a combination of #1 and #4. I built my own client base that was loyal to me while I was working for a law firm, then when I made the leap to start my own firm, many of those clients came with me. I also worked on networking with other attorneys in the community so that I had a good referral base. It helped dramatically that I wasn’t making a huge salary before I left my prior firm job, so I didn’t need to match a huge prior income, I kept my costs of my new firm down, and my wife carried the benefits with her job so at least our benefits were covered.

  27. Hi Corbett,

    I’ve talked to people who have done 1-4. I, myself, have been doing a variation of #1 and it is a killer – but worth it in the beginning. One thing I’d like to add is that if you have ideas and aren’t exactly sure where to take them, definitely start on the side. Yes, be prepared to be exhausted. It’s just that way. But it’s also really exciting, and that eases the exhaustion. Also, starting up slowly when you are testing ideas is a good thing. This also can ease exhaustion and give you time to get feedback on your project(s). Once you have a handle on what you are doing, and need to start putting all your effort into your own project, then I’d say it’s time to take a leap of faith. My own leap of faith starts next month, when I will begin working full-time on my business.


    • Suzanne, what are you planning on doing in a month? Would like to follow your story. I just announced my leap of faith today, and I’m wondering how I will feel 6 months from now.

  28. Option 1 is the strongest option especially if you have time at work to “veg” when everyone else is wasting time shooting the bs waiting for the day to end YOU go HARD.

    its rough though make sure you are not being monitored by haters because you know they are going to hate.

    what are you waiting for?

  29. I started by doing an hour or so after work but struggled with being so tired and it took forever to get anything done.

    Being an electrician I resigned from my job and became a self-employed electrician so that I could do 4 days of electrical work and 3 days of internet marketing. Over 12 months my IM work helped me get higher paid electrical work so that I could work 1 day per week which paid all the bills.

    This gave me much more time for internet marketing, but I also noticed that the more time I had available I was procrastinating more… I was jumping from training to training, strategy to strategy and building most of the time rather than promoting. I fell into the trap of thinking I had all this time available…

    I then hired a coach and the first thing he got me to implement was keeping a track of what I was doing every hour of my work days. After doing this for a few days I quickly realised how much time I was wasting… I created a default schedule of essential tasks that needed to be completed each day (using Google calendar and the repeat feature) and these tasks had to be completed before anything else. That simple trick worked extremely well…

    Ian McConnell
    Western Australia

  30. Hey Corbett,

    I too am working on option #1. I’ve never before made a website so it was slow going at first but as of late things seem to be speeding up! I have a great job doing a radio morning show so I get off the air at 10am and I’m out of the building at noon with practically my whole day to work on my side business!

    I have to say thank you for all the motivation! I found you a few months ago and you are part of the reason I finally took action. I “wanted” to do what I’ve begun for years now and thanks to you and another blogger I finally took action and I am so glad I did.

    Thanks for all you do and please keep it up!

  31. I took the ballsy leap and am living on savings right now – none of the other options worked for me, and my Intuition was telling me to jump. I get the same question all the time – “How did you do it?” “Easy, I just did.” isn’t a valid answer for most people! I’m working on my version of the same post. Thanks for sharing – good info.

    • Katie, how long has it been since you took the leap of faith? I just announced mine this week, and I’m curious to know my own future, but of course, I can’t! :)

  32. Hi Corbett,
    I just wanted to drop a line and let you know just how much your posts have helped to realign my life. I too have taken the plunge and have carved out a little bit of internet real estate to call my own.

    Thanks again for helping me find the courage to begin again at 50!

  33. I did the fourth option about 3 months ago, and the stress factor is just now starting to kick me in the butt! Terrifying! Great post.

  34. Gosia

    Hi Corbett,

    I am also working on option #1, although I must say it has a lot of downsides. It is not so much that I lack motivation because I have a steady job, it’s the tiredness that I find difficult to cope with. I am currently the only one in the household who is earning money and I can’t reduce my normal working hours which stresses me out because I never have enough time to look after my business. If it were possible I think I would go for option #4, at least you can give yourself a year to see whether it’s going to take off or you’re better off finding something steady again. Great post though, very interesting to see all these different points of view!


  35. @Jessie. I completely understand what you’re experiencing.
    I wish blogs like this had been around when I went straight to option 4 12 years ago!! Only I took the leap without savings. It’s really strange ‘cos now I look back I think my god did I really do that? At times it was sheer hell but I know that I now wouldn’t be doing what I’m doing if I hadn’t. Sometimes happiness is more important than money in the bank but at the same time there has to be some balance.
    Great food for thought.

  36. Corbett: Right now in my life I am satisfied with the way things going. Not very many people know what I do and who I am, but I am working to change that. I finally found my passion and that gives me happiness. Some of us are lucky enough to find our passion at a young age, but I did not get to be that lucky. Now though, I am trying to make up for some of the lost time.
    I think that option number one is the best option if you are happy with the way things currently are in your life. If not, then maybe a leap of faith is the best option.

    Awesome post and nice site!

    Best wishes,
    William Veasley

  37. Hi Corbett.

    I started out with #1, working on my side business (and continuing my education). It’s been a bit of a struggle with a full-time job, especially with the associated overtime and a 2+ hour daily commute.

    Reading this blog post inspired me; I was able to successfully negotiate a 25% reduction in hours (and pay) which will free up the time I need to continue to grow my side business and eventually lead to the life I want. I know the tunnel is long, but now I can see the light in the distance.

    Thanks so much; this post was the catalyst I needed!


    PS. Also the following two posts were particularly helpful: and my favorite

  38. Love this topic and just announced my retirement and wrote a book entitled, “How To Engineer Your Layoff: Make A Small Fortune By Saying Goodbye”.

    Number 1 lesson I have for you folks is: NEVER quit your job! Figure out how to get laid off. The amount of money you will get is potentially huge!



  39. Clark Humphrey

    What if you don’t already have a high paying job to give up?

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