Considering Entrepreneurship? Here's the REAL Stuff You Need to Know.

Considering Entrepreneurship? Here’s the REAL Stuff You Need to Know.

Everyone that has been around this site for the last year or so has a good idea about how I feel when it comes to side-hustles. I think any young person with a brain and a computer that wants more money should at least try one.

A lot of people disagree with me on that, but as per usual around here…I don’t really care haha.

The “entrepreneur life” is REALLY appealing to Millennials. I get it. I freaking LOVE working for myself. But I want everyone to understand that when I tell them to get a side-hustle, it’s to supplement their income and pay down debt or get ahead.

It’s not so they can bail from their job like I did to run M$M.

I started Millennial Money Man at my in-laws kitchen table after work back when my wife and I were living with them. I had finished paying off my student loans, and was really fired up about $$$ for whatever reason.

From there, it’s blossomed into this thing that I run from my computer wherever I want making $8-10k per month. Sounds so cool right? Well, it is. But it’s not for everyone, and it’s not nearly as easy as most people think from the outside looking in.

Working for yourself has killer advantages, but if you like working 9-5 and literally NEED video games or Netflix to “let off steam” and turn it all off…full-time entrepreneurship may not be for you. Just hear me out.

Here’s the real stuff you need to know about working for yourself:

The day you quit your job is the scariest day in the world.

I didn’t ease myself into being self-employed. I took that leap of faith that is the barrier of entry  to entrepreneurship for most people. I literally added up all the money I had on my phone calculator to see if I could make it work, made the decision with Coral (my wife), and then walked in the next day and quit my job.

Yes, I’m crazy. But it’s also what makes me good at this.

I had a full-blown panic attack at 3:00 am the next morning. I’ve never had anxiety in my life, but for about 20 minutes I swore I was going to straight-up die from a heart attack. That’s what happens when you rip the security of a steady paycheck out of your life.

Health Insurance Sucks

I totally thought I was just going to jump on to my wife’s school insurance, but that was laughable at best. Our monthly insurance premium would have jumped up to $800/month for two high-deductible plans. So, I picked up a plan from the marketplace (not subsidized) with a $6,000 deductible that seemingly doesn’t pay for jack.

I’m 28 and basically a “non-user” in insurance companies’ eyes, but that doesn’t mean I’ll get a great policy. This is not a political post in any way – so please don’t turn it into one in the comment section. I’m just telling you right now that insurance isn’t great for self-employed people.

Every month starts at zero.

Last month I made $10,172.27 from my computer. You can check it out on my income report here. However, that was September. September doesn’t mean crap in October.

That feeling of security most people have with their paychecks every few weeks is a tangible thing. You absolutely get used to not having a guaranteed income out on your own, but it takes time. Really consider that if you are thinking about quitting your job in the near future (I know a lot of my readers are).

There are no “hours”.

The three things about self-employment that I mentioned above are probably a little concerning to the average person, but if you need to turn your mind off after work you need to pay attention to this:

There is no turning off with entrepreneurship. It’s not sexy. You can’t vacation all the time. It doesn’t just fade away when you want it to.

I wake up at 5:30 am and immediately check my phone and emails (after my normal 2:30 am wake up to do the same). I look at my social media pages constantly throughout the day. I respond to every comment and message at any hour.

It’s totally common for my attention to drift to my business mid-conversation with my wife (which is definitely no bueno with her). Even when we took a vacation to Jamaica earlier this year, I had my computer and a crappy internet connection to stress me out the entire time.

Entrepreneurship never goes away, and there is no off button. Think about that really hard if you’re thinking that working for yourself would be incredible. If you STILL think it’s a good idea and have a dream to do it – go for it, but respect the game or you’ll be miserable.

Question for you:

  1. Self-employment or steady pay and security: Which do you prefer?

Live differently. Your bank accounts will thank me later. ~M$M

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17 comments… add one
  • FinanceSuperhero Oct 26, 2016, 8:04 am

    Awesome analysis and questions to consider, Bobby. Right now, the answer for me is “both.” I am not quite ready to make the jump and leave behind the guaranteed income which my salary affords for a couple reasons.

    1. I value my sanity. I know that if I were to shift to full-time entrepreneur through a combo of blogging and real estate hustling that I would probably descend even further into workaholism. I think I just made up a word there, but you get my point.

    2. I respect my wife. She isn’t comfortable with me walking away from my day job’s salary and benefits, and if I’ve learned anything behind married for six years, it is that I should listen to my wife 99% of the time.

    Do I have what it takes to be a full-time entrepreneur? Yes. I know I could do it. The desire just isn’t there, and as you’ve pointed out in the past, if you don’t want it badly enough, you’re not going succeed.

    • Millennial Money Man Oct 26, 2016, 8:11 am

      Yeah I think that a lot of people have what it takes to be an entrepreneur, but the cool thing is that it doesn’t need to be full-time. The internet has made having a small business in addition to your day job very accessible.

      I don’t feel like I work a lot, but my wife says I work all the time. Good problem to have I guess haha!

      If your wife isn’t comfortable with it at this point, don’t do it! Definitely making the right decision by listening to your wife…I’m sure Coral wishes I did that more often 🙂

  • McClain Oct 26, 2016, 9:46 am

    Great article! Pretty eye opening on how it really feels to be on your own. For me eventually I want to get there (not willing to jump in like you did yet, haha, but maybe someday). In my eyes (and I have zero experience with this so you would know better than I) I’d rather work for myself, I’ll take the bad with it, to not have to work for someone. The article definitely helped me understand it a little better though!

    • Millennial Money Man Oct 26, 2016, 11:09 am

      Yeah don’t jump in like I did, or at least let me know so I can dig in to ALL of the pros/cons with you. I created a really ideal situation for myself before I made the leap.

      I love working for myself – I was honestly not a great employee because I wasn’t happy doing what I was doing. If you are a full-blooded entrepreneur, working for someone else feels like you’re trapped!

  • Financial Panther Oct 26, 2016, 10:00 am

    I think you make a good point about the vast amount of work that goes into entrepreneurship. A lot of people have this idea that when they control their own time, they’ll somehow work less. The opposite is true though. When you go the entrepreneur route, your work day is 24/7.

    • Millennial Money Man Oct 26, 2016, 11:05 am

      Working less is definitely possible, but so far in the beginning of my business it hasn’t been a vacation or anything like that haha! I enjoy my life a ton and don’t feel like I’m working when I am, but a lot of businesses aren’t that way at all.

  • Aliyyah @RichAndHappyBlog Oct 26, 2016, 11:12 am

    I’m two weeks into it and I’m already exhausted, lol. The fact that you start at $0 each month is the scariest part.

    • Millennial Money Man Oct 26, 2016, 11:32 am

      It is scary! My wife just kinda rolls her eyes at me when I start freaking out at the beginning of the month. Always seems to work out as long as I keep putting in the time though.

  • Mrs. Picky Pincher Oct 26, 2016, 1:47 pm

    Thanks for the insight! I’d love to be a full-time blogger someday and it’s good to know what to expect. Dude, I had no idea aobut the health insurance thing! That totally sucks!!

    I don’t think it’s for everyone since you basically have to be “on” all the time. Hell, I took one day off from the blog to move to my house and I swear everything broke during that five-hour block of time!

    So while I prefer the security of a paycheck, I’m not above going off and doing my own thing. But I admittedly wouldn’t do it unless my spouse had a regular job–just in case.

    • Millennial Money Man Oct 26, 2016, 1:59 pm

      My wife having a job was a huge reason I made the jump when I did. It would have been super tight financially and ultimately depressing if this turned out to be a failure, but knowing you literally won’t starve helps.

      The insurance thing was a huge shock. My wife was paying less than $100/month for her insurance plan through the school, but just adding one person in her district took it up to that ridiculous $800 level. Every person I’ve told that to has been shocked so far haha. Makes no sense but it is what it is.

  • The Accountant Oct 26, 2016, 2:52 pm

    Great post! As an accountant, I have to point out that you are also paying employer and employee taxes on your individual income and depending on the classification of the business you run, you may be paying corporate taxes. It’s something a lot of people don’t realize before they go into business for themselves. You also don’t get taxes taken out of your paycheck, so you have to do some extra work with estimating quarterly tax payments. While still completely manageable, it’s another aspect that entrepreneurs have to consider before taking the leap.

    • Millennial Money Man Oct 26, 2016, 3:35 pm

      Absolutely! I need to have an accountant come on the site and detail some of that information. I’m set up as a LLC with a S-Corp designation – I think getting a great accountant to help you set up your tax structure is huge!!!!

      • The Accountant Oct 26, 2016, 5:44 pm

        I”m no tax expert (I was on the audit side when I was in public accounting), but from my limited knowledge (and not to get too technical) LLC with S-corp designation is the best way to go. LLC limits personal liability and the S-corp passes the income/loss through the business to the owners (aka no corporate “double” tax). Definitely worth having someone good set you up!

  • Dani Oct 26, 2016, 9:47 pm

    What a great post Bobby. Currently I’m still working monday to friday from 8 to 5 and wondering whether I should stay in this job I’ve been doing for the last 10 years while doing side job or just focusing on it and quit my job. So many things to consider. Thanks! I would like to share the post on my twitter timeline. 🙂

    • Millennial Money Man Oct 27, 2016, 10:40 am

      Hey Dani! I’d grow the side thing and see what happens! If it fails, you’re good. If it kills it, you’re good. 🙂

  • Kimball Hansen Oct 28, 2016, 11:51 pm

    Dang Bobby. This blog, specifically this post is exactly what I’ve been looking for. I’ve had an itch for the past few years that won’t get scratched.. But I’m stuck in the middle: I value security and steady pay but I’m getting all ancy-nancy and wanting to branch out and do my own thing. How can I figure out which one I ultimately want? And if you can’t answer it because it’s up to me to decide then I understand.

    • Millennial Money Man Oct 29, 2016, 7:43 am

      Do both at the same time! I started M$M when I still had a full-time job. Whatever you are wanting to do, start small and work on it when you get home from work. If it gets to the point where you are making comparable income to your real job from your side-hustle, start considering if it could work full-time! Hope that helps 🙂

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