Thoughts on Self-Employment After 3 Years

Whelp. It’s now been 3 years since that fateful day of being let go and jumping into blogging full-time (anyone still reading from 2010?), and as we cross the 6 Million page view mark, I can’t express how grateful I am to still be here.

Who knew a blog could change your life?? :)

Throughout these past few years however – and really, the past 6 overall – I’ve learned a lot and continue to do so almost every single day. I haven’t seen anything evolve so fast as the internet’s been doing this past decade, and I’m glad we’re all here right now taking advantage of it :)

Here are a handful of things I’ve learned over the years:

  1. It’s incredibly rewarding being able to do what you love every day.
  2. Even though half of the stuff I do is just as annoying as the stuff everyone else has to do :)
  3. It’s often more stressful than a “regular” job too – at least those I’ve ever had. (Especially when you’re the sole provider for your family)
  4. And speaking of family, they pretty much think you goof off all day and will call/drop by anytime they want because apparently when you’re home that means you’re not working.
  5. But that can be fun sometimes too :)
  6. And can give you a nice break from hustling 24/7.
  7. Which is probably the hardest part of the job – there’s no “turning it off” switch.
  8. But it is awesome to be able to set your own schedule.
  9. And work in your pjs. (though warning: you always feel/are less productive when doing so)
  10. Lately, it’s also starting to get a bit lonely (I work from home).
  11. And going to coffee shops only takes you so far.
  12. I also have to continually remind myself that work is not the most important thing in the world.
  13. Nor is my “brand” or twitter account, or anything else us bloggers obsess aver. (See also: stats)
  14. It’s wonderful being recognized in your own field, but I’m thankful it doesn’t carry over into the “real” world. No one knows, or even cares, who you are offline – it’s freeing.
  15. Also, I’ve stopped telling people I’m a blogger when asked what “I do.” They never understand, so now it’s “online consultant.” No one knows what that is either, but they always shake theirΒ  heads in agreement and move on to the real reason they asked: so they can tell you what THEY do ;)
  16. With freedom, also comes analysis paralysis. It’s often times hard to focus when there’s no limits.
  17. On the plus side, when you finally DO know what you want to harness your energy on, you can start doing so *right* away.
  18. But the money flows all over the place, so it’s important to stash it away when the times are good. There’s less stability working for yourself.
  19. On the flip side, the rewards can be much better. I once made $22,000 over a weekend for probably 12 hours of work. (And then, 2 years later, lost $8,000 on a new idea/project).
  20. You can deduct a lot more than you think with a home office too.
  21. And you feel like you’re in a “special” little club with other entrepreneurs. Even though it’s just as “special” as any other job out there ;) (If we had signs on our fronts saying who was self-employed, we’d give each other high fives when walking by each other – similar to how motorcyclists and jeep owners acknowledge each other on the road)
  22. But you also have to deal with insurance and quarterly taxes for having the pleasure.
  23. And doubting yourself, then praising yourself, and then doubting yourself all over again.
  24. When you become successful at one project, you also think you’re going to be successful on all of them (you’re not).
  25. And you fail a lot more times than you succeed.
  26. But, the times you succeed make you forget about all the failures! ;)
  27. It’s definitely not for the faint of heart.
  28. Nor, for *everyone* – contrary to what many entrepreneurs like to say.
  29. Working for yourself is not the only way to define success either. What makes you HAPPY, does. At least to me… In career, love, and life in general.

So, I’ve pretty much learned a lot over the years :) And I honestly couldn’t tell you where I’ll be this time next year, or any of the years afterwards for that matter. I love my job, but I also love a bunch of other stuff in life too (and I’m no stranger to switching jobs! ;))

What I DO know, however, is that I just want to be happy. Whatever that looks like. Right now that means working for myself and continuing to grow our family, but perhaps it’ll look different later. Perhaps I’ll go back to 9-5 one day, or maybe I’ll continue blogging for the next 30 years when it’s not even called blogging any more. Who knows…

But right now? I am happy. And blessed to be able to write a post like this. I never saw this lifestyle coming, but the world works in mysterious ways if you keep your eyes open. And that’s probably the biggest lesson learned throughout this whole experience: being prepared for when opportunity knocks (and *knowing* when it’s indeed an opportunity, too).

Thank you guys so much for being a part of this journey with me throughout the years! And supporting all my crazy projects! :) You can’t have blogs (professionally)Β without readers, so I thank you from the bottom of my heart.

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Word-press photo by J$

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  1. Dee @ Color Me Frugal December 23, 2013 at 5:48 AM

    Congrats on your success! I hope that in three years I can write a post like this as well! Awesome job on creating such a great blog.

    1. J. Money December 23, 2013 at 3:41 PM

      Thanks Dee! I hope you can too! :)

  2. Clarisse @MakeMoney Your Way December 23, 2013 at 6:04 AM

    I can really relate with this “Number 22. And doubting yourself, then praising yourself, and then doubting yourself all over again”. Sometimes I’m so proud of myself because I think I did a great job but then sometimes I feel so very depressed that I think I’m not good at all. :)

    1. J. Money December 23, 2013 at 3:40 PM

      There’s a psychological thing too called “Impostor Syndrome” that people like us get every now and then :) Where we basically feel like our achievements aren’t actually achievements for one reason or another, and we’re “fooling” people into thinking we’re something we’re not. I def. have that at least once a week! Haha…

      1. theFIREstarter December 24, 2013 at 9:18 AM

        Wow… thats an interesting link J!
        I’ve had pangs of that over the years… how weird that there is a syndrome named after it (although I guess there is one for everything nowadays!)

        Looking at your list, I would definitely take the rough on there to get the smooth, so hopefully I’ll be somewhere, anywhere near where you are in 3 years also! You are right though it’s clearly not for everyone!

        Good luck for future learnings!

        1. J. Money December 27, 2013 at 11:26 AM

          Thanks! Good luck to you and your endeavors too, my new friend :)

  3. charles@gettingarichlife December 23, 2013 at 6:14 AM

    Hey J,
    You’ve shared with your readers all the chances in life you’ve taken, some more successful than other. But you got that hustling spirit. Like Wayne Gretzky said you miss 100% of the shots you don’t take. Here’s to a kick ass 2014.

    1. J. Money December 23, 2013 at 3:42 PM

      You too my friend! I like that quote too – haven’t heard that before.

  4. Mike Collins December 23, 2013 at 7:22 AM

    I’m totally swiping #15, people ask what I do online and look completely dumbfounded when I try to explain.

  5. Liz December 23, 2013 at 8:12 AM

    Congrats on 3 years! What a huge accomplishment. It is really inspiring to see someone who has made blogging work as a career. Hope to say the same thing some day!

  6. Laurie @thefrugalfarmer December 23, 2013 at 8:30 AM

    Happy, happy bloggiversary, J$! Thanks so much for all that you’ve shared with us and taught us over the years. You really are making a difference. I had to laugh at number 4. This is SO my mother, whom I adore. She calls several times a week and says “Hi! Whatcha doing?” “Ummm, homeschooling 4 children, running a freelance business and trying to keep a house. Other than that, not much.” Gotta love her. :-)

    1. J. Money December 23, 2013 at 3:47 PM

      Haha, right??? Mothers are funny like that :)

  7. Brian@ Debt Discipline December 23, 2013 at 8:31 AM

    Online Consultant does sound Sexier! Continued success J!

  8. a terrible husband... December 23, 2013 at 9:06 AM

    “And work in your pjs. (though warning: you always feel/are less productive when doing so)”

    Note to self. Putting on pants benefits me and everyone around me. Got it, oh wise one.

    Congratulations on three/six years! Oh… and to answer your question, I’ve been here since 2009. Keep up the awesome work!

    1. J. Money December 23, 2013 at 3:48 PM

      Saweet! I can now come over and visit you then, since you probably aren’t doing anything right now anyways :)

  9. Ben @ The Wealth Gospel December 23, 2013 at 9:15 AM

    Congrats J! And thanks for being a big part of the inspiration for me to start my own blog. I’m looking forward to one of these posts a few years from now ;)

    1. J. Money December 23, 2013 at 3:48 PM

      Glad you’re up and running too, my man :)

  10. Fig December 23, 2013 at 9:20 AM

    Congrats on 3 years! I haven’t been doing it nearly as long but I’ve already learned a couple of those lessons too. I hope you continue doing whatever makes you happy in life and that it brings you great success J. Money! :)

  11. Kim@Eyesonthedollar December 23, 2013 at 9:36 AM

    Knowing when to take an opportunity is huge. It takes a special something to jump when everyone else is hanging on for dear life. We all fail, it’s just that successful entrepreneurs use failure as a lesson and motivator, while most people just give up. Congrats on your success!

  12. Ree Klein December 23, 2013 at 9:53 AM

    Amazing list, J! I’ve been at this blogging thing for just over a year now. I didn’t take down my “coming soon” page until March of 2013 because I was terrified to let people know some of the stupid mistakes I’d made w/r/t money. Especially my family who I’d kept in the dark about those aspects of my life!

    You’ve accomplished so much. Just read about your LoveDrop project; so amazing and inspiring. Your site is awesome, too. Thank you so much for listing one of my posts there…I’m honored to be represented!

    Thanks for sharing what you’ve learned…I’m inspired and ready to make major progress in 2014.


    1. J. Money December 23, 2013 at 3:53 PM

      Thanks Ree! And congrats on finally taking down that “coming soon” page ;) Though admittedly it’s probably much harder to do when you’re putting your real self out there vs. going anonymous like I do!

      Just got your email too – will hit ya back in a few :) Thanks for stopping by, and for the kind words!

  13. Stefanie @ The Broke and Beautiful Life December 23, 2013 at 9:56 AM

    Congratulations! Good point about the “off” switch. I feel like I’m always “on call” with my blog, and it’s not even a major source of income yet.

  14. John S @ Frugal Rules December 23, 2013 at 10:11 AM

    Congrats on three years J! Love the post and can relate to a lot of it as I’m about 2 years into it myself. I never thought we could be successful at running a business, but love the freedom, though it doesn’t always feel freeing at times. ;) I can completely relate to #15. We tell people that we run an advertising company and at least 75% of the time they tilt their heads and say what do mean by advertising?

    1. J. Money December 23, 2013 at 3:54 PM

      Just tell them it’s like Mad Men ;)

  15. jolie December 23, 2013 at 10:47 AM

    wow that 3 years went by fast!! You have taken something that could have been a devastating curveball, and turned into a world of new experiences and opportunities. You should be very proud of the way you have inspired so many others.

  16. Lance at Money Life and More December 23, 2013 at 11:32 AM

    Congrats J! A big accomplishment indeed! Keep up the awesome stuff and have a Merry Christmas!

  17. Karen at Money Saving Enthusiast December 23, 2013 at 11:53 AM

    Glad you are a blogger. Glad you are happy. Now drink and be merry. ; ) off to my “unplugged challenge”. I’m breaking it to day hi here.

    1. J. Money December 23, 2013 at 3:54 PM

      I’m so proud of you for going for it!! I’ll admit I’m a bit fat chicken ;)

  18. Karen at Money Saving Enthusiast December 23, 2013 at 11:54 AM

    Sorry for the typos again. LOL

  19. Matt Becker December 23, 2013 at 1:29 PM

    Thanks for the inspiration man! I hope that I can write a list like this in a few years as well. Guess I should be getting back to work!

  20. Joe December 23, 2013 at 2:28 PM

    I remember that post! Has it been 3 years already? Time really flies. I was in my cubicle at work and I was really happy that you got out of there. It showed me that it can be done.
    I’m happy now too. Life is so much better when you can do things on your own term.

    1. J. Money December 23, 2013 at 3:55 PM

      Oh wow, so cool to hear! A lot of things can happen in a few years if you put your mind to it :)

  21. Justin @ RootofGood December 23, 2013 at 2:43 PM

    Happy 3 years of freedom, buddy! Hope you have 3 times 3 times 3 more good years.

    Even though I’m nothing more than a mere hobbyist at this blogging thing, it’s fun. I can see why some turn to online entrepreneurship as a full time career.

  22. kathleen December 23, 2013 at 2:45 PM

    What a great post! Happy anniversary, and Merry Christmas!

  23. Jacob December 23, 2013 at 5:30 PM

    J. Money, congrats on surviving 3 years in online entrepreneurship! I already know the pressure of a single income home with a day job, being an entrepreneur is a whole other level of awesomeness.

    Merry Christmas, Happy New Year, and keep on rockin’ it!

  24. Blake @ BeanCounterbyDay December 23, 2013 at 5:33 PM

    Congrats on your success! There are so many people out there that just float through life, never really finding something they love to do. It is a great story every time you see someone having success and enjoying every second of it.

    I started as a CPA almost 8 years ago, and realized this year that while I enjoy my co-workers very much, my passion doesn’t lie with my current career. So I’ve used the last couple of months of this year to begin groundwork on two passions of mine. One day, hopefully I’ll be able to look back on a successful trail like you can.

    Merry Christmas!

    1. J. Money December 24, 2013 at 8:40 AM

      Sounds exciting! What, pray tell, are these two passions of yours? :)

      1. Blake @ BeanCounterbyDay December 24, 2013 at 4:24 PM

        I’m taking the professional athlete market by storm baby! I get to talk finance and sports every day, and who better to need financial planning help than recently wealthy 22-year olds!

        1. J. Money December 27, 2013 at 11:26 AM

          Nice!! Sounds like a perfect concoction. Let me know if I can ever help with anything :)

  25. Michelle December 23, 2013 at 8:52 PM

    Congrats on 3 years! Here’s to many more :)

  26. Dear Debt December 23, 2013 at 10:15 PM

    You are doing a great job and thanks for sharing your insights here. I can imagine it can be lonely and hard at times. I get so stuck inside my head at times, I think I’d be extra neurotic if I was self-employed. It’s nice to know it’s possible, for people that aren’t self-employed. You are right, keep doing what makes you happy, and if something changes, you change.

  27. Christine @ ThePursuitofGreen December 23, 2013 at 11:32 PM

    Been reading from 2008! Hehe. On and off and now more so than ever! Lovely run-on super long poem thing you created above.

    Love number 4! When I was freelancing everyone thought I didn’t do much and just was home all day doing whatever I wanted. Even people in my industry who I would have lunch with would then ask me “So what are you doing later today?” I would answer “work…” and they would be like “Oh yeah…”

    Totally understand the loneliness part, its great to have some human interaction.

    1. J. Money December 24, 2013 at 8:42 AM

      You might have the record for the longest reader! WOO! Thanks so much for being a part of it this entire time – we’re now 6 years older! Haha… :)

  28. Mike December 23, 2013 at 11:57 PM

    Congrats on the 3 year anniversary. It’s certainly an accomplishment! I’m sure the best is yet to come.

  29. Agatha December 24, 2013 at 12:44 AM


    I’ve read all of your posts =P love the way you write — and you are very inspiring. I wish you the best in everything you do, as long as that involves you keeping on entertaining me and making me think [or not, you know, if something else makes you happier]!

    1. J. Money December 27, 2013 at 11:29 AM

      Awww, haha…. thanks :) I def. plan on being online, and entertaining, so hopefully I won’t let you down ;) Thanks for reading!!

  30. Katherine December 24, 2013 at 3:16 PM

    To relieve some of the loneliness, have you looked into joining a coworking group/space?

    [Maybe someone else has suggested this in the 40+ comments above]

    1. J. Money December 27, 2013 at 11:31 AM

      Hey Katherine :) I’ve actually tried it once before, but only lasted a couple of months… mainly because I had to commute a little to get there and didn’t like waiting to work in the mornings. I’d be up for trying again if it were somewhere close by, like walking distance, but currently no places like that around here. Excellent idea though! Thanks for stopping by :)

  31. Becky @ RunFunDone December 26, 2013 at 12:02 AM

    I love this! My husband is self-employed, and sometimes I get really jealous of him, because he works way fewer hours than me, and can go snowboarding whenever he wants. But, I also like the stability of my boring 9-5 job, and would probably be an anxious nutcase if I were self-employed. Your reflections tell both sides of the story! Good luck to you in 2014! :)

    1. J. Money December 27, 2013 at 11:31 AM

      Thanks! To you two as well :) May your husband take you on more snowboarding adventures this year!