Entrepreneurship, Money, and Donuts

What up what up! Was digging around some emails and came across a little note I sent to myself a year ago that said: “share this around or something – you did a great interview!” Haha…

So today I shall comply and do just that. You know, to not let my previous self down :) I’m not sure it’s my best, but I do know tons of people are struggling to “figure it all out” right now work-wise, so maybe this will shake something up for y’all. Lord knows it takes us time to sort things, and even when we DO finally get our $hit together something else comes up to challenge it!

Anyways, hope you enjoy it. Big thanks to WiseBanyan for letting me republish this today. Check ’em out if you’re looking for some investing help… They say they’re “the world’s first free financial advisor,” but I think they forgot about blogs ;)


J. Money currently makes six figures a year through blogging, being a blog/money coach, and advising financial startups. But before getting to that point in his life, he held over 30 jobs and got laid off more than once. [Update: I no longer do coaching, but it was fun when I did!]

J. was kind enough to give us some insight into what it takes to be an entrepreneur, why getting fired doesn’t have to be the worst thing in the world, and the truth about making money on the side job hopping. Take a look!

Job hopping is getting more common these days, but it’s still looked down upon. What would be your advice to someone young and restless thinking about making a quick job switch?

I think it’s fine to switch jobs so long as you’re truly going after your goals and not just chasing the money or a title.

It’s so easy these days to get sucked into wanting more just because it’s what society tells us, but when you realize you can be just as happy – and still grow! – without job hopping all over the place, it becomes a much more positive, and peaceful, experience. And believe me – after having 30+ jobs myself before “figuring it out,” it’s a world of a difference!

Just do your best to go after the right things, and whether you have to job hop or not at least you know you’re on the right track.

Everyone says build up 3-6 months of savings as an “emergency fund,” but would you give any other financial advice to people in case of a layoff?

Yeah, the more savings you can bank the better, but something even more beneficial is having a side hustle or two in the works. That way you’ve always got an income stream coming in whether large or small. God forbid you do lose your job you could always dedicate more time to your side hustles and keep up the flow of money while you’re out on the prowl for a new one. IF you even need a new one!

My little blog I started years ago went from making $0.00 a month to fully supporting a family of four and ending up changing my entire life. So you never know what other opportunities can arise from your side hustles. And even better if you can get passive income streams going which don’t even require any work on your behalf once you get them up and going!

You were actually relieved when you were laid off. For people who are pretty upset about it, what would be your go-to plan (both emotionally and financially)?

When it comes to being financially/emotionally ready, the best thing you can do is have as much of a foundation set before a time like this ever occurs. That means getting debts paid off, savings banked, an overall sense of good financial management, and general life goals. All easier said than done, of course, but believe me – it’s easier to get working on this stuff now versus later when you lose your job! That’s always a shock whether you’re prepared for it or not.

What about people looking to start their own business?

If you’re even remotely interested in starting your own business, I strongly suggest getting started with it now on the nights and weekends while you have that stability and income flowing in.

You will fail and learn a ton in the process, and if you’re not willing to spend your free time now growing a business, you’re probably not a good candidate for self-employment.

You’ve got to want it bad, and it’s much easier to take risks now while you’ve got nothing to lose than later when your livelihood counts on it. And these days you don’t need business cards or fancy business plans to get things rolling – just focus on getting as many “yes’s” as possible by pitching people (i.e. clients) and then build out the company from there! It’s all about that lean startup mentality until you get things rolling.

Would you say entrepreneurs in a sense are always at risk for getting “laid off?” due to out-of-the-box thinking?

Hell yes! No job – or business – for that matter is ever 100% secure. You always have a boss, it’s just a matter of whether it’s a manager above you or a paying client. In either case a strong work ethic and creativity go a long way in securing your future. And the more times you get up after failing the better you get over time too!

Working for yourself isn’t all rainbows and donuts – it’s just a trade off of pros and cons.

Any other money/general advice for people in their twenties feeling queasy about the job market?

YES! If you get a good grasp of your money early on, the “job market” or economy or anything else matters much less as time goes on because you hold all the power. So being conscious of where your money is going and doing your best to prioritize can make all the difference in the world. One of the best ways to get on top of it all is to start tracking your net worth (assets minus liabilities).

It’s quite empowering knowing where you stand, and you can’t measure success if you’re not tracking anything. So track your net worth on a monthly basis and then really challenge all your expenses and see what’s truly important in your life. Remember that the less you need to live off of, the less you need to earn.

Once you become financially free almost all the events in the world matter less and less with time. And so does needing a job for that matter!

You’re a dad now! Do you have a key piece of advice regarding jobs and careers you plan on telling your child in the future?

I want them to experiment like crazy and work on whatever it is that they’re passionate about!

You always produce better work when you’re excited about a project, and these days with technology and the internet the options are really endless with what you can build. I still hope they get a college degree to fall back on throughout the process, but at the end of the day if they can wake up and be excited with how they’re spending their time, I’ll be one happy and proud father.

I never want them thinking there’s only one path to success, or that they have to do whatever everyone else is doing. Most everyone else is stressed and in debt :)


Here’s to figuring it all out!

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  1. Brian @ Debt Discipline February 13, 2017 at 6:08 AM

    Still holds up even after all this time. :) Some of the same advice I recommend. I like have at least 1 year worth of cash in an e-fund, and that varies depending on your monthly budget. Always have the plan B cooking. You never want all you eggs in one basket.

    It’s something I’ve express to my three children, what things can you do on the side to make extra cash so if you do choose to work for someone else you do need to feel like it the only way you need/have to make money.

  2. Mrs. Mad Money Monster | @madmoneymonster February 13, 2017 at 6:15 AM

    Awesome interview! Thanks for sharing. I, too, want the same thing for my 7-year old daughter. I told her I want her to do whatever she wants to do for a career, but I never want her to “have” to do anything. Passion is top priority when you have all the basic necessities covered. :) I just wish I had focused more on this stuff 10 years ago. As for now, time to get ready for that W2. Hahaha. Hopefully only for a few more years!

    1. J. Money February 13, 2017 at 9:45 AM

      Haha I know… if only we ALL had our epiphanies sooner than later.

      At least we finally got them though :)

  3. FullTimeFinance February 13, 2017 at 7:00 AM

    Fantastic interview. It’s so interesting to read about the many paths people took to becoming an entrepreneur. What field where you in before you went to blogging?

  4. Freedom 40 Plan February 13, 2017 at 7:08 AM

    Some great advise, thanks for sharing. In particular I like the point about it being OK to switch jobs so long as you’re truly going after your goals and not just chasing the money or a title. Maybe particularly relevant to me right now as I’ve found myself trapped on the later part of that statement, but trying to move more towards my true goals.

    1. J. Money February 13, 2017 at 9:48 AM

      It’s a hard one. I struggle all the time even with this blog stuff cuz it’s SO EASY to chase the $$ but can come at the loss of putting out good quality or slapping ads all over your site. And reading blogs over the past 9 years I can tell you that more people are starting to chase the $$ than actually blog :(

  5. The Green Swan February 13, 2017 at 7:15 AM

    Good point about job hopping, J. I see too many folks continuously jumping within a year from job to job. It doesn’t take too long before their resume looks like a mess and HR managers start asking more questions. It’s important to have a purpose and strategy which each new job. Coincidentally I published an article about the subject and my personal experience job hopping today. Check it out! Thanks J$.

    1. J. Money February 13, 2017 at 9:51 AM

      Hah – cool timing, will check out.

  6. Go Finance Yourself! February 13, 2017 at 8:16 AM

    Great advice here on starting multiple streams of income. By not having all your eggs in one basket, you can alleviate a lot of stress. If something happens with one source of income (i.e. you lose your job) you have other sources of income to help you stay on your feet.

    It’s incredible how common job switching has become today. I think a lot of it stems from short-term views people take and the feeling that the grass is greener on the other side. If it’s a move that furthers your career and provides more opportunity for the future, then I say go for it. But many times I see people giving up a good opportunity at their current job for more pay at another job. Sure they may earn more money right away, but they may be kicking themselves for lost opportunities at the previous job in a few years.

    1. J. Money February 13, 2017 at 9:50 AM

      It seems to be much more tolerated and accepted these days too, so furthers the hopping even more I’m sure!

  7. Josh @MoneyBuffalo February 13, 2017 at 8:31 AM

    Thanks for sharing this interview. Lots of great nuggets. We are 1+ year into our entrepreneurial journey & having as much money banked up is very important. But, as you mentioned about trying to establish your business while still gainfully employed is even more so.

    If my wife hadn’t done that with her income stream, I would have needed to find traditional employment again. I first idea fizzled out & now I’m doing something different (teaching) as my primary income stream now.

  8. Kalie @ Pretend to Be Poor February 13, 2017 at 8:40 AM

    Great career advice! I really like how you point out that no job or business is 100% secure. We experienced staying too long in a “secure” job at a big company with great benefits and pay, where marketable skills really weren’t being developed.

    I also like your point about having a side hustle option as well as emergency savings in the case of a layoff. Having something to fill some of the gap is so important.

  9. Paul February 13, 2017 at 8:56 AM

    Job switching is fine. Its incredibly naive and short sighted to think that you are anything but a vessel for a company to profit off of. If they didn’t make money off of your effort you would not have a job. You are nothing to your company but a debit or credit… I have had many jobs myself, and how I explain it is that I left for career progression. People have said to me it looks like I job hopped early in my career, I tell them that I am not the guy that will sit and wait his turn. If the company can keep up with me then I will stay, but as soon as I feel like I am being held back I’m looking for a way forward. No false pretenses, they either are looking for someone with potential or they are looking for a body.

    A company being loyal to its employees, that is a myth. Or at the very least a relic of days gone by. Opportunity means nothing, never stay or joins for an “opportunity” because that may or may not ever happen. Unless there is a plan in writing all an opportunity really is, is a flat out lie from a potential boss or human resources dept.

    I have had 19 jobs, I’m in my mid 30s and every single time I switched I got paid more. It wasn’t all good, there were some choices that turned out to be in hindsight maybe not the right ones. But it forced me to step up my game. In the end it was worth the experience.

    1. J. Money February 13, 2017 at 10:00 AM

      Yup – only reason people hire us is to increase their own bottom line. But if you’re a job hopper I’d imagine it’s one more hurdle to overcome in an interview next to the guy who isn’t – so all your reasoning (and debate skills!) will come in handy :) And believe me, I’ve had to use them myself over the years.

      1. Paul February 13, 2017 at 2:23 PM

        Yeah, it really wasn’t bad, every single HR person basically just said oh ok, looks like each of these job changes show career progression. I said, yep, that was that.

        I work for myself now, so I answer to clients not managers. Its better for me this way, I don’t know if I had it in me to sit through one more performance review…

        1. J. Money February 14, 2017 at 6:17 AM

          Haha… I didn’t mind those so much as ALL THE MEETINGS EVERY DAY!

  10. Mike B. February 13, 2017 at 9:12 AM

    Every “no” is one step closer to getting that “yes”; which means the inevitable probability of failure in entrepreneurship. I look at stories of people who made it, and they all involve some degree of hardship or struggle along the way. Nice interview, J$. Very sound advice for those with the fires in their bellies!

  11. FinanceSuperhero February 13, 2017 at 9:16 AM

    I’m a big fan of the advice for children. None of us can even begin to pretend that we know what the future economy will look like 10, 15, or 20 years down the road. But those who find a passion and genuinely enjoy what they are doing will find a way to be successful in helping others and earning a living.

  12. Mrs. Picky Pincher February 13, 2017 at 9:23 AM

    I’m guilty of job-hopping (oops). I know outwardly job-hopping makes you appear immature and flighty, but my reasons for leaving were different. Each time I took a job I was desperate to get out–I didn’t bide my time and wait for the right job to come along. As a result, I worked at some really, really toxic and nasty places. I had to abandon ship because some jobs made me physically sick. Anyhoo, there are a lot of reasons for job-hopping and, even though it looks bad, I wish people knew there are many reasons for doing so. Being a millennial isn’t always one of them.

    1. J. Money February 13, 2017 at 9:55 AM

      Physically (or mentally) sick is definitely a good reason to job hop!! No shame in that AT ALL.

  13. Joe February 13, 2017 at 10:11 AM

    Great interview. Interesting answer about the kids. I’ll tell my kid to experiment too, but do it smartly. If you’re good at something, then concentrate on getting better at that. Probably avoid going for low paying careers unless you’re really good at it.

  14. Mrs. BITA February 13, 2017 at 10:51 AM

    I really need to work on additional streams of income. I’ve relied on income from my full time job my whole life (it _has_ been a good income, so I can’t complain), but I feel like I don’t know if I have what it takes to generate income from some other source. My investments are starting to count as a second stream now, but they don’t quite satisfy the itch I feel to prove that I can make money myself from something other than my day job.

    1. J. Money February 14, 2017 at 6:19 AM

      investments most definitely count!! and probably the easiest way to make money without doing work :) hustling on the side is good, but it’s not a requirement to be successful/wealthy/retire early. just helps speed it up of course (and adds extra protection).

  15. Ms. Montana February 13, 2017 at 10:56 AM

    I have little tolerance for doing things I hate (especially if I don’t really care about it, and it takes 40+ hours of my week). Life just seems to short for that. Keeping our expenses low, and having some passive income plus extra cash, means we just get to do stuff we love. We can try a bunch of things, quit the ones we don’t like, try new ones, and put time into the good stuff. And once you don’t need much income, it seems like 100 cool new options magically appear.

  16. Stephonee February 13, 2017 at 11:31 AM

    Having a side hustle or a freelance gig to lean on was clutch for me. The first time I was laid off, some former coworkers of mine launched a Kickstarter and invited to hire me to help out with their brand new business. This really helped close the gap with freelance work for them, until I landed a full-time job.

    The second time I was let go from a job about a year later, I had kept up working for my friends on the side. I was able to walk into their office the next day and say “Hey, I’m available full time now! Put me to work!” and I’ve been doing steady work for them ever since, but also keeping up other freelance work on the side of that! It’s so much more secure to have multiple streams of income. It’s like, having a bunch of levers I can pull. If one falls through, I can just pull the other levers!

    1. J. Money February 14, 2017 at 6:20 AM


      1. Stephonee February 14, 2017 at 9:45 AM


        (this is why I don’t do domain name arbitrage)

  17. Sylvia @Professional Girl on the Go February 13, 2017 at 11:41 AM

    Great advice! When I was told that my contract wasn’t being renewed back in 2014, I completely shut down. I didn’t have an emergency fund saved, I hadn’t been looking for a job because I thought they would renew it and I had just booked a trip to Jamaica for myself and my fiance (now husband). So I ended up accepting the first job that came along (I left two years later) because 4 months of no income while bills continue to build up was extremely stressful. I just use that time in my life as lesson learned and now I always try to have a Plan B.

    1. J. Money February 14, 2017 at 6:22 AM

      did you at least have fun in Jamaica when you were there? :)

  18. Amanda @centsiblyrich February 13, 2017 at 12:05 PM

    There is so much to love about this interview, but I REALLY love your wishes for your children! I’m so with you on that. If my kids take a non-traditional path, I’m totally okay with it. I want them to do what they are passionate about and what brings them joy. Of course, I want them to be responsible (financially and otherwise) at the same time, but finding true happiness is my wish for them.

  19. Primal Prosperity February 13, 2017 at 1:01 PM

    I’m a total job hopper myself, so ‘financial flexibility’ was a big priority for me in my late 30’s. Now, I just claim that I’m on the corporate ‘lattice’ instead of the corporate ladder. :)

  20. Smart Provisions February 13, 2017 at 1:52 PM

    Great interview, J$. I’m a frequent job-hopper (3 jobs in 2 years). I agree that job-hopping is bad for the resume, but if done well, it could increase your salary by over 20% with each job hop.

  21. Finance Your Goals February 13, 2017 at 4:39 PM

    I think job hopping can be beneficial and is essential to build skills, figure out what you want to do, and necessary to increase your income.

    A piece of advice I received from a former boss when I was contemplating leaving my job was to make sure to always move toward something. I’ve found myself in professional ruts and ultimately pulled myself out by finding something new to move toward (vs. just wanting to leave the job that was unfulfilling). Even when you’re in a good position and/or happy with what you’re doing I think you should look to see what else is out there and pursue new opportunities.

  22. 2 Rivers Properties February 13, 2017 at 5:09 PM

    I have to agree that you’ve got to want it bad to start your own business. I remember when I started my real estate company in 2010 I would work my regular job during the day time and then spend my evenings showing houses, dealing with tenants, and paperwork.

    Starting a business is never an easy task but if you hustle hard and long enough eventually it all pays off. Thanks for the post :)

  23. Kraken Fireball February 13, 2017 at 6:10 PM

    I like the thinking that no job is 100% secure. It keeps me on my toes and away from the normal complacent insecure lifestyle, which is how I think most people get into financial trouble in the first place. Thanks for sharing this interview that I missed out on the first time around.

    1. J. Money February 14, 2017 at 6:31 AM

      Yup! And even when you’re self-employed too!

  24. ZJ Thorne February 13, 2017 at 8:25 PM

    This wisdom stands the test of time. Thanks for re-sharing it.

  25. Liz February 14, 2017 at 5:34 AM

    My father did something very similar when I was growing up (pre-internet days) – he would work on some evenings and weekends helping friends with their painting businesses. When he got laid off from his corporate job, he transitioned into the painting/wallpapering/powerwashing/ceiling business full time. Having those side hustles let him transition into a full time business where he eventually made more than at that corporate job. I don’t do job hopping myself-I was with my prior company for 12 years and this current one for 6 – but I do believe strongly in diversifying income streams. A company can decide anytime they don’t need your services anymore, and you need to be prepared.

    1. J. Money February 14, 2017 at 6:32 AM

      Smart father :)

  26. Anders February 14, 2017 at 7:58 AM

    Nice article and thanks for a good blog!

    I’m rather new here so I’m not sure how old your children are.. but are you trying to teach them to have a good financial sense too?

    I’m asking because I’ve got a daughter who is almost two years old now, and I’m planning to do my best to teach her as much as I can of what I know (and what I learn) about economy and finance. I was just wondering if you’ve had a plan for teaching your kids, or if you hope it will just rub off on them since you’re on top of your money? :)

    Take care!

    1. J. Money February 23, 2017 at 3:14 PM

      Oh – I plan on them taking over the family business one day! So they better be learning about it! :) They’re currently 2 and 4, so we have a ways, haha…

  27. Daniel Palmer February 14, 2017 at 5:21 PM

    Especially like your entrepreneurship on nights and weekends advice. Like everyone else on this earth, I’ve got this burning passion to create business. But yes, the stability of a day job is nice in the mean time.

  28. AJ Money Matters February 17, 2017 at 7:28 PM

    I can totally resonate with this entire post! I’m in my mid 20’s and was just made redundant. Luckily I’ve been taught good money practices form an early age and don’t have to stress too much at the moment. I really wish though they taught a bit pf personal finance in high school, as you never know when you may be out of a job or how long for. I never thought it would happen to me, but it did.
    Having said that though, I do feel completely inspired to really work on our own financial blog and expand it. I feel like my mindset is shifting to thinking more outside of the box now and getting more creative with ideas. Your 20’s is such a great time to take risks and I think it’s all to do with how you approach situations and the power of positivity.
    Very inspiring post :)

  29. Chris February 19, 2017 at 10:10 AM

    Thanks for sharing!
    My favorite response: YES! If you get a good grasp of your money early on, the “job market” or economy or anything else matters much less as time goes on because you hold all the power.

    My wife and I have been talking with our six-year old son about money and saving and opportunity cost…it’s been an interesting process as I sometimes feel like I’m talking in circles and confusing him more than anything. The way you put it about getting an early start is the point I’m trying to get across. Trying is the operative word here. :-)

    1. J. Money February 23, 2017 at 3:16 PM

      Haha… well if you figure out the magic way, please do let me know as I haven’t had much luck either :)