3 Signs You're Ready to Become an Entrepreneur

3 Signs You’re Ready to Become an Entrepreneur


I will NEVER forget the feeling I had when I drove away from the band hall for the last time. It was basically the last step I had taken to become an entrepreneur. Obviously, it was really freaking scary, but at the same time…I felt like I was free.

Don’t get me wrong, I had a pretty sweet gig as a band director. The school I worked at was SUPER supportive of the band program. The funding for the band was great, and I was allowed to purchase a ridiculous amount of high quality equipment for the kids to use.

Even with all of that, I never felt right at my job. I saw how passionate the other directors were, and I felt out of place.

Before I dive in to this list, it’s important that you know I’m not telling you to quit your job tomorrow, even though I talk about working for yourself a lot on this site. One of the most terrifying thoughts for me is that M$M will create a bunch of “leap of faiths”. There’s not anything wrong with that, but it takes a lot of planning and hard work to pull off what I’ve done.

That decision should not be taken lightly.

Here’s three signs you’re ready to become an entrepreneur:

You feel like you’re suffocating at your job

This was the biggest thing for me, and suffocating is the only way I can describe the feeling (sorry if it seems too dramatic haha). Waking up every day with that feeling of  “Ugh I don’t want to do this” got old pretty fast for me. Even if you’re good at your job, a lack of passion will keep you from being bad@$$ at it.

For me – not having passion was a disservice to the kids I was teaching. Me leaving my teaching job was just as much about making sure they had a teacher who would do ANYTHING for them as much as it was about starting my own business.

You’re daydreaming about business like crazy

Beer brewery. House flipper. Even a pool company. Those were just three of the MANY business ideas that I thought about constantly. For whatever reason, I had wanted to own some kind of company since I was in college. The problem for me was that I couldn’t figure out what I wanted to do!

**Fun fact – I actually came very close to starting a pool company instead of M$M. I spent several weeks during one of my summers helping a pool company owner I know installing heaters and cutting PVC pipe to see if I would like it.**

If you find yourself constantly thinking about the types of businesses you could own…it may be time to start your own. 🙂

The vision of yourself 20 years from now isn’t right

Seriously – take a second and picture yourself in 20 years with the same job or line of work that you have right now. If it seems kinda jacked up and disappointing, that’s a pretty big sign that you need to start hustling more for whatever it is you want to do.

Here’s the thing I LOVE about entrepreneurship: It doesn’t have to be full-time. Some people give me crap for this – but I honestly believe that every person that wants to should try starting their own business on the side. The worst thing that could happen is that it fails miserably. So what if it does? (Pay your taxes or it can ACTUALLY be bad and have real consequences!)


Business ideas don’t have to be complicated. I’m obviously a gigantic fan of online businesses (especially for millennials), but there are so many cool ways to make extra money – and you NEVER know what they can turn into. M$M was something I started and worked on after I got home from work.

It’s still just a blog…but who the hell knows how big this thing could get someday?

If you have a job and love it – cool. Entrepreneurship is not for everyone, and there are a ton of things that are a total pain in the @$$ that are never an issue for people with traditional jobs. If you’re miserable and know that you need to be out on your own, stop talking about it and do something.


Questions for you:

  1. What is your dream job?

  2. Have you ever tried a side hustle?

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

Don't miss another M$M post.

Sign up for the M$M newsletter to get new posts sent directly to your inbox when they go up on the site. As a bonus - I'll send you reviews of my favorite free personal finance tools and ways to make extra money with a side hustle!

We won't send you spam. Unsubscribe at any time. Powered by ConvertKit

34 comments… add one
  • Mrs. Picky Pincher Sep 21, 2016, 8:06 am

    Ahhh, I love daydreaming about doing what I love. I do think entrepreneurship would be a lot of fun, but it does involve some risk and outside-the-box thinking, and I guess that’s what’s holding me back. But nothing was ever achieved by staying comfortable. 🙂

    • Millennial Money Man Sep 21, 2016, 8:26 am

      Yeah for sure – I don’t want to downplay the risk at all. It is REALLY SCARY. Even now that I’m making some decent income online, I still have little freak outs when I think a few months down the road. Nothing is guaranteed, but that’s a normal thing that happens to self-employed people.

      You’re trading risk for opportunity.

    • Ryan Johnson Oct 10, 2016, 1:18 am

      I know this nagging feeling of wanting to do something else.

      When I was 19 I quit my terrible retail job to play poker for a living , which I did for five years. I remember punching the air cartoonishly as I left my last shift!

      Having a side hustle is challenging and rewarding! It pushes you to improve things and you learn a lot.


  • Financial Panther Sep 21, 2016, 8:55 am

    I agree with you that everyone should at least try an entrepreneurial side hustle. With the way technology works now, there’s so many ways to be a part time entrepreneur with very little risk. Even renting out a room on Airbnb or driving for Uber is an entrepreneurial endeavor that you can do in your spare time. If it’s not for you, just move on to something else.

    • Millennial Money Man Sep 21, 2016, 9:39 am

      Yep, no reason to not try in my opinion. The internet has opened up SO much possibility to start a small business on the side. It’s a great way to get ahead financially if you work hard.

  • Tyler Sep 21, 2016, 9:00 am

    Bobby get out of my head. I am thinking about the business I already run all the time and how much more I could be doing for that well at my 9 to 5. I’m really good at my job just don’t have the drive to do it anymore, and to be honest it’s obvious by how i work well there, or rather don’t work. Great article man.

    • Millennial Money Man Sep 21, 2016, 9:35 am

      Thanks Tyler! Haha this is just the kind of stuff that I think about all the time. Keep hustling and grow your side thing until it’s a NO BRAINER to bail. I don’t recommend quitting your job early like I did. Too many variables going my way I think. Nice work!

  • Mike B. Sep 21, 2016, 9:34 am

    I like the other ideas you’ve tossed out, and I’ve acted on similar ideas of my own. Not that starting a blog isn’t a small business in itself. It is, as I’ve learned in recent months. And is something that needs to be “acted on” too.

    • Millennial Money Man Sep 21, 2016, 9:37 am

      Absolutely! Blogs are a tough business to get started, but they can make money IF you have a killer message and treat it like a business instead of a hobby.

  • Millennial Moola Sep 21, 2016, 11:37 am

    My dream job is probably something like Dave Ramsey or Suze Orman where they just take calls from listeners all day about money and I get to pontificate about what they should do. That sounds like a pretty chill existence, and check out Ramsey’s house it must pay well too

  • Brandon Sep 21, 2016, 1:47 pm

    I was thrown off the cliff, as opposed to taking a leap of faith. Around 2013-14, I worked at a marketing agency. I was unhappy and constantly daydreamed about turning my photography from a hobby to an actual business. I gave myself two years to save some money to start up, but my job let me go a month or so later. That was my sign that I needed to pursue my dream.

    Sometimes you jump, sometimes you’re pushed, and the landing hurts like hell either way. My photography business has grown, I’ve learned a lot and gained (mostly) steady work, and I’m now branching out with an Etsy store. Even with all the scratches, I’m thankful that I was pushed.

    • Millennial Money Man Sep 21, 2016, 1:54 pm

      Nice Brandon! Congrats man. I know those first few months suck – you don’t make any progress, you get turned down and fail constantly…but then it starts to change for the better. Good luck moving forward!

  • Mike @ Super Millennial Sep 21, 2016, 4:21 pm

    Great post and congrats on all the media coverage lately, well done! I definitely have “the fear” right now so I’m stashing away for the day it happens in the future. More money saved, less stress & hopefully more productivity. Totally agree side hustle is the way to start and get your feet wet, blog & book are my first attempts. Slow & steady because in 20 years I KNOW I won’t be doing the same line of work as now haha.

    • Millennial Money Man Sep 21, 2016, 6:22 pm

      Exactly Mike!!! Thanks, it’s been pretty cool lately I’m not going to lie haha. Side-hustle is the way to go. Low-risk, just takes extra work.

  • Finance Solver Sep 21, 2016, 9:38 pm

    I daydream about having a successful blog like crazy. But the thing that I love about blogging is that I can do it on the side instead of taking such a big risk and quitting my job tomorrow. I invest about 20 hours a week into my blog and I love it! Very low risk and high reward, now that’s something I can get on board with. I don’t think it’ll ever happen where it will be a business but time will tell.

    • Millennial Money Man Sep 21, 2016, 10:06 pm

      It is low risk! I don’t even know what kind of time I put into it anymore honestly. It’s WAY more than people realize though haha!

    • Mystery Money Man Sep 22, 2016, 9:09 am

      You never know, it’s amazing what others have done with blogging! I’m new to it myself, but it’s amazing how many other ‘side hustle’ ideas I’ve been brainstorming ever since. My primary focus remains on building the blog, but I’m planning on branching out to other ventures in the next 6-12 months! Great post MMM!

      • Millennial Money Man Sep 22, 2016, 9:19 am

        Thanks! You’re right – it’s pretty crazy. If you would have told me I’d be making more blogging than I did teaching this soon I would say you were crazy! Very surreal.

  • JIm Sep 22, 2016, 4:13 pm

    My dream job would be a job that I could show up for at the crack of 10:00 and nobody would say anything about it. Check my portfolios of stocks for an hour or so till it was decision time on where to eat lunch. Then take a two hour lunch with friends. Then get back and check stock market again before it was nap time. Then check and see how the market closed for the day. All while collecting $60K a year in cash dividends and growing my net worth by $22K a month (on average).
    I know it would be hard at first, but somebody has to do it.
    Living the dream….

  • JIm Sep 22, 2016, 4:58 pm

    And Yes, I have tried several side hustles as I grew up and into my thirties.
    In second grade I sold cold sodas to construction workers in my neighborhood out of an ice chest that I pulled with my wagon. (15 cents for one or two for 25 cents)
    In eighth grade dish washer ($1per hour)
    Mowed lawns in seventh grade ($10 for front and back including edging) Note: weed eaters had not been invented yet.
    In college installed peep holes in doors in high crime areas. ($20 each)
    Early twenties striped parking lots at nights and weekends (bid jobs, made good money)
    This is just a few of my side hustle jobs that come to mind now, but I am sure there were more. All on top of my regular jobs.
    Sometimes you have to just “Do the hustle”

    Be safe on your trip… very nice view from the hotel.
    While you are there you can use my boat if you want to (pier 21 slip 10) “Living the dream Too”

  • Mrs Groovy Sep 22, 2016, 8:42 pm

    Great post, Bobby. Thanks for sharing. I know there are many ways to make money blogging but how do you evaluate the ways you want to, and choose to earn money? We’re getting advertising offers for sponsored posts, but that route doesn’t seem so appealing. We got Google Adsense going right out of the gate but put a stop to it. It just bloated up our website. How did you find the options that fit your values?

    • Millennial Money Man Sep 22, 2016, 9:04 pm

      No problem Mrs Groovy! I turn down a lot of sponsored posts…probably 70%. The key for me is to only allow companies that sell something I would buy or agree with. Once you do one, the social media managers talk to each other and you get more offers (that’s my theory anyways haha).

      That’s why I’m diving into affiliate marketing. It’s the EASIEST way to pick products that I think are great. You’ll also find that as you keep growing, the quality of advertiser gets much better.

  • Matt Spillar Sep 23, 2016, 1:10 pm

    These are great tips Bobby! I really admire people like you and J$ (among many others) for taking that leap and starting your own business. I think some people who daydream about what it would be like to leave their jobs and work for themselves fail to realize all the challenges that it comes with. For me at this point in my life, I really like having a steady paycheck I can count on, routine that I know what to expect during a work week, and then getting to blog and work a second job on the side. It’s busy, but I’m happy and fulfilled. Basically my point is that entrepreneurship isn’t for everyone, and some people daydreaming about “the grass being greener” should take stock of their current situation. It’s worked out great for you, but people need to not forget all the hard work, the struggle, the long hours, being unsure about having enough money coming in, etc. that you’ve had to deal with in building this site to where it is today!

    • Millennial Money Man Sep 23, 2016, 3:26 pm

      YES!!!!!!!!!! Dude you nailed it Matt. Blogs are deceiving – people don’t realize that when they visit these sites, they are literally looking at months and months (years for J$) of content. It’s very easy to think that it’s an easy gig that just takes a few clicks and some writing here and there.

      There is nothing wrong with regular jobs and the safety that comes with them – it takes a certain type of person to do the whole leap of faith thing, and MOST fail. I consider myself so fortunate that I am making a living this way. The way that you are doing it is absolutely the responsible way to pursue an online business IMO.

      I think J$ got fired, which is definitely a cooler way to start a blog than I did by just being a crazy person and quitting. 🙂

  • Ten Factorial Rocks Sep 25, 2016, 10:27 am

    Good post MMM. However, people see only the glory side of entrepreneurship – due to survivorship bias. The odds of entrepreneurship success should not be over-estimated just because you have some bad days at work.

    • Millennial Money Man Sep 25, 2016, 11:01 am

      Thanks – I understand your position on this, but I’m encouraging people to try starting a small business on the side and disagree with your thinking wholeheartedly. If people try and fail on the side while keeping their day job…so what?

      • Ten Factorial Rocks Sep 26, 2016, 12:11 pm

        Nothing wrong with trying something on the side and failing as you say. The real risk and true opportunity cost comes if you quit your job to pursue this full time without fully understanding the odds of entrepreneurship success. Side hustles, done with zero opportunity cost (as you still have the job) and low investment, are not what I covered in my article. That’s the smart way to enter this space.

        • Millennial Money Man Sep 26, 2016, 12:35 pm

          I agree! I don’t encourage people to quit their job the same way that I did. Some people will see my story and make the leap, but I can’t control that. The only safe way to make a living online is to start on the side and transition when the income is substantial enough for a consistent amount of time to live on.

  • The Savvy Couple Feb 16, 2017, 6:12 pm

    Totally ready! After jumping around from job to job since graduating college. It’s my year to become 100% self-employed. Trying to grind to make that happen.

    Kind of stuck between a hard spot though. I actually went back to school to get my home inspection license in NYS. I really want both our blog and inspection business to take off. It’s tough to allocate enough time to each. So far it’s been about 70% blog and 30% inspection business.

    Tough decisions are ahead but the fact that self-employment is becoming more and more real is the most exciting thing ever. #Borntobefree

  • thecollegecapitalist Feb 16, 2017, 11:38 pm

    Man, sounds like you’re living the dream! I’m starting to follow in your footsteps and just spent quite a bit of money to set up my own domain (http://thecollegecapitalist.com/). I’m now posting content to try to help the younger generation be smart with their money. Who knows where it will take me! I really hope to see the same success that you have achieved, and your story is incredibly inspiring. I must admit, as I sit through my college courses (I’m a junior), I am CONSTANTLY daydreaming about starting my own business, and I really hope this website I have created will take me there. Do you have any tips for me as a young blog/business? It can really feel overwhelming at times. Thank you so much, and may the cash flow plentifully 🙂

Leave a Comment