Life After Quitting Questions Answered: Saving, Business-Building and More

There are SO many questions (both in real life and from online people) that are swirling about what the heck I’m gonna do once I quit my job in New Haven. It’s about 2 months from go-time, so things are getting real. A lot of people are curious what I’m doing next. I hope this post answers some of that.

While I’m sure no two people would approach things the same way, I hope this gives you some idea of the types of things you need to think about, too.

Why are you quitting your job?

The simple answer is that my girlfriend is finishing grad school at Yale in May, and we’re both itching to get out of New Haven. Even if we wanted to stay, there’s pretty limited opportunity for jobs. New Haven is an alright place, but I wouldn’t really recommend it as a place to live if you have the choice of anywhere.

Are you going to get another job?

If the right opportunity comes along, I’ll definitely jump on it.  In case it doesn’t, I’ve saved almost half of my income from my job every month for several months now so that I can have savings to live off for several months. I estimate that I have about 5-6 months of living expenses (assuming no income) earmarked for this life change. At the same time, I have some income and I’ll be working to increase how much I make.

If you’re not getting a job, how will you make money?

I’ll be honest: I don’t have that entirely figured out yet. My SEO consulting is starting to gain more traction (got a new client last week), but it’s still not close to replacing my full-time job income. I do earn some money from this blog, and I’ve dabbled in freelance writing as well. I’d certainly consider working in a part-time capacity for someone if it allows me to both learn and stay location independent.

This whole thing sounds scary! Aren’t you afraid?

Honestly, not so much. I subscribe to the “what’s the worst that can happen?” mentality in cases like these. I don’t see too many awful scenarios that are realistic. I could go broke, but I doubt I’ll end up homeless or starving. I could move in with family or friends if I got really desperate (although I’d have to be pretty desperate for that to happen).

Being broke at 26 years old isn’t the worst position to be in (and many Americans are already far, far worse off). I’m not saying I want that to happen, but I’m not afraid if it does.

How will you make a down payment on a house?

Hah! Sorry to laugh, but I don’t plan to buy a house for some time. Here’t the short list why:

  1. I have no idea where I want to settle down yet
  2. I value mobility.
  3. I have no desire to have a mortgage payment
  4. I like the life of a renter and not having to worry about random surprise costs like repairs.
I wouldn’t be surprised if a lot of people my age don’t plan to buy. In fact, a recent survey showed that only 7 percent of respondents thought owning a home is an important part of the American dream! Times are a-changin!

What about health insurance?

I haven’t chosen a plan yet, but I’ll probably opt for a high-deductible plan. Based on some quick research and recommendations, it will cost around $200 a month. I’m sure there’s almost no benefits to this type of plan unless I’m severely sick or injured, but are there many more affordable choices in America? Healthcare kinda sucks in the U.S. Aside from that, I have no health problems, and I only rarely visit the doctor.

I thought about COBRA from my current employer, but I’m guessing it will be too expensive for it to be worthwhile. I’ll be sure to check on what the cost would be for me before turning it down.

How will you save for a wedding?

This is the total cop-out answer, but I still hate the idea of spending $20,000 on a wedding. Realistically speaking, it doesn’t look like I’ll be able to afford anything close to that anytime soon. A fancy wedding just isn’t one of my priorities right now.

How are you planning to invest for retirement?

I’m not, for right now at least. I outlined how I’m not investing in the stock market right now (although I did max out my Roth IRA for 2011 if that calms your nerves a little). I’d like to continue to make at least some sort of regular contribution for retirement, but I have to put that temporarily on the backburner. I’ll revisit this once I’m earning some sort of a livable income and not relying primarily on savings.

Where will you live?

I’m not sure yet. There are many options on the table, like NYC or Portland. My fantasy is to be a little bit of a nomad (that’s the whole point of this location independent thing for me, after all). It will almost certainly be a large city that isn’t San Francisco. Ideally it would be ultra bike-friendly.

Do you have any clue what you’re doing?!? Sounds like you’re ruining your life!

I appreciate your concern, but no, I can’t say I have a well-laid out plan for myself. But I’m okay with that. While I am a planner at heart, I enjoy changing things up and not having life be so predictable.

Do you have any more questions for me? Just about anything is fair game, and I’m happy to answer 🙂
$ $ $ $
photo by: Steve-h


  1. financiallyc says

    How will you save for a wedding? Really, do people ask that question? I can easily think of 1,000 better ways to spend money than on a wedding.

  2. Ha, it’s been almost a month now since I quit my day job and I did it because I wanted to save more..crazy and scary but I couldn’t be happier 🙂 

  3. Great post Jeff. People always want to judge you within THEIR frameworks, but you understand the value of changing the rules. It’s amazing what can be accomplished when you ask “what’s the worst that could happen?” and go for it.

  4. Just Do It, Jeff.  The methods you are using sound solid, and I think a lot of the questioning that you’re getting is really from people who just can’t get past the conditioning that we’ve all grown into.  Get a degree, get a job, work til you retire.  Being able to break away from that and go it alone is still very foreign to so many people.  You can always get a job later too, but you’ve just got to give it a try.

    • Thanks, Shane. I know you’ve been going through a similar thing lately. I definitely hear you on getting a job later. I’m not giving a whole lot up now, and I know the options will be there later.

  5. Glad that you’ve got a plan jeff – i subscribe to your risk mentality as well – i mean sure you could DIE, but that’s going to happen anyway.  Go for it, but my suggestion is not to be a TOTAL bum.  having a pittance of income coming in (not even online income, but another source from possibly a lawn mowing gig) could really help extend the savings you’ve got and allow you to get you to a replacement income from your current sources.

    •  @Jeff Sustain Life Blog Thanks, Jeff. I’m definitely not against part-time work, and I think that’s a great idea to keep things going. I don’t want to let any menial jobs get in the way of being location independent or succeeding with my larger goals. Outside of that, I’m open to anything that keeps the dream alive.

  6. inbudgetswetrust says

    This is so gutsy, but I think it’s a great move.  Good luck!
    I have a post queued for tomorrow about the options I considered when I realized I would have to pay for my wedding on my single income… but the spoiler is that the destination wedding option proved right for us.  Our friends married at a destination last year, and I think the cost to them was only $7,000 for a week in the Dominican Republic and all the guests had a blast!  I also would’ve been okay with a backyard wedding, but I wasnt’ the only one making the decision 😉

    •  @inbudgetswetrust Hah, yeah, I gotta admit that making a gutsy move makes me feel kinda cool.
      I like the idea of a destination wedding, too. I guess the main argument against it is that not everyone can afford to travel or can take the time off. But there are drawbacks to any plan for sure.

  7. Jeff, this is an amazing opportunity for you! You are definitely brave, but have made provisions, and no matter what, you are right what’s the worse that could happen? At 26 you have your whole life ahead of you and I assure you there are many worse off :0

  8. Congrats! This is definitely an interesting and awesome opportunity for you. Good luck going forward.

  9. I love how you just laid this all out… Hey, there are many worse things in life than having no plan. Like having a plan that makes you hate your life. I think it’s going to be great – you know what your values are, which is probably the more important part of the equation.

  10. Do it! Being hungry will make you hustle! Wedding’s can be on the cheap and what you learn running your own businesses will be invaluable later!

  11. Good luck to you!  You are going about this with a great attitude, and I have no doubt that, whatever you do and wherever you are, you will be a great success!

  12. MilkThePigeon says

    This is awesome man. I love reading “i’m quitting my job to do what I’ve always wanted” posts.
    You said you’re going to be heading out west yeah?  I think I remember talking to you about heading to WDS.
    In any case, good luck man it’s awesome to hear that you are making the jump.  I can’t wait to be doing it myself too! 
    I’m moving somewhere by late June too, wherever I end up you’ll have a free place to stay!  In any case It’ll probably be China or Spain, hope you haven’t been to either haha.

    •  @MilkThePigeon Thanks for stopping by, man! Glad you enjoyed the post. Yeah, I’ll be out at WDS, and I hope I can check out Portland for more than just a weekend.
      I’m looking forward to reading about when you take off again. Thanks for the offer, and I’ll gladly extend the same one to you! I’ve been to Spain and would gladly go back, and China is definitely on my list to check out, too.

    •  @MilkThePigeon I do too.  It’s very fun and liberating to hear people’s stories of freedom. 

  13. Weddings and stuff can get expensive, but it’s also a once in a life time thing. Love reading these sorts of posts. 🙂

    •  @InvestItWisely Haha yeah. I didn’t mean for the weddings thing to steal the show from this post, but it’s just something people have been asking about. Thanks for dropping by!

  14. JeffreyMissesBoston says

    Boston is bike friendly.

  15. Congrats on the new direction! My wife and I didn’t want to spend a lot of money on a wedding so we just went to Vegas. 🙂

    Great idea on not looking for a mortgage. Hold off as long as possible.

    •  @Bennyhsu Hey Benny, thanks for stopping by, love your blog!
      As funny as it sounds, I could definitely see myself doing a Vegas wedding, too. And yeah, definitely won’t be getting a mortgage soon. I love the flexibility of renting way too much.

  16. Hey Jeff!  What’s wrong with San Francisco? lol.  We are SUPER bike friendly for a big city!  Look up “Critical Mass” etc.
    I would seriously turn the after burners on and figure out ways to increase revenue aggressively.  B/c after that, there are operating costs and TAXES to deal with.
    But, if the GF is going to be a Yale grad, maybe you don’t have to stress as much?!
    Best, Sam

    •  @Yakezie Haha I know San Francisco is a great place to live and is bike friendly. That was a poor and vague comment on my part, and I just made it because San Francisco is all I’m hearing about from soon-to-be Yale grads these days.
      Yeah, believe me, increasing income is definitely a priority for me. I’m doing something to work on it every day now.

  17. frugalportland says

    Congrats — and remember, when people say mean things, it’s not about you, it’s about them, so between the lines “you are crazy this will never work” you’ll see “gee I really wish I could do what you’re doing”

  18. Congrats on the new direction! My wife and I didn’t need to spend much money on a wedding so we just went to Vegas. 🙂 fantastic concept on not looking for a mortgage.

  19. Congrats on the new direction! My wife and I didn’t need to spend lots of money on a wedding so we just went to Vegas. 🙂 fantastic idea on not looking for a mortgage. Hold off as long as possible.

  20. Nice Post! We created Hot Stone Communications because we believe that brands in the health, beauty and wellness space need a healing treatment. We heal them by transforming their marketing efforts from an expense into a strategic investment. <b><a href=” “>healthcare marketing agency </a></b>

Speak Your Mind


Read previous post:
Can a Personal MBA be just as good as the real thing?

After earning two degrees and wondering if a master's degree is always worth it, I've searched and considered many other...