I had a hard time sleeping last night, I was mostly letting my mind run about this particular blog post which it very difficult to relax and finally pass out.

I’ve now been self employed since late August 2016, it’s been an interesting 8 months. I wanted to share some of my own personal experiences and things that I’ve learned while transitioning into self employment.

Lessons Learned About Self Employment

Self Motivation, Exercise & Time

One of the biggest challenges I’ve come across is getting motivated every single day to always want to work. My ultimate goal was freedom, right?

I’ve found myself some days waking up as late as 10am and getting the day started very slowly where as other days I’m up between 5:30-6am and I can get a ton done in those extra 1-2 hours in the morning before I sit down in my office.

Most of my morning routine is pretty much the same, I wake up and feed our 3 cats and then try to get in a home workout in front of the TV.

I signed up for a gym membership in January for the first time in over 5+ years. I was started out going 3x a week following a program by Kinobody which I thought was good, it was more just the motivation to wake up and want to get dressed to go to the gym. I’ve always had a thing about leaving the house without showering first and of course it makes absolutely no sense to drive to the gym after taking a shower just to come home and need another one after doing a workout.

I decided to go back to a classic workout I did years and years ago called Insanity, it’s a 60 day workout that is pretty much 100% cardio and using your body for some muscle building exercises like push-ups. When I did it years ago I was in amazing shape and lost noticeable fat while building muscle. I’m about 3 weeks in and so far it’s more the challenge of dealing with missing some workouts some morning and just feeling like you’ve “messed up” the schedule. I’ve typically just been picking up where I’ve left off and my goal is to get at minimum 3 workouts in a week (the program calls for 6 a week).

Beyond working out and waking up early I also have found myself trying not to just let myself slip into bad habits that will take away from getting more done. The biggest being video games, when the Nintendo Switch came out I went out the day of launch and managed to walk into a Target down the street and impulse buy the console with the new Zelda game. I ended up sitting home the entire day on a Friday and the following Saturday just playing it all day.

It’s nice to sometimes let loose and just relax for an entire day but I’ve often found myself feeling guilty about doing something like this when I could have been more focused on generating income to achieve the real freedom I desire.

I’ve overall been gaming a lot less during the week and I try to keep it to the weekends only with friends.

My Living Space

Being at home everyday can be a bit daunting, I’m probably filling up my gas tank on average maybe once a month now that I’ve gone self employed. I’ve always been more of a ‘home body’ but not needing to leave for an actual day job has definitely increased that.

The biggest thing that I find helps me being home all day is I’m able to get a lot more done around the house in terms of keeping things clean, doing chores like laundry and just actually enjoying the environment I’m in. I recently decided to tear out the carpet in my office and put in brand new laminate floors, with the combination of new paint I did last year my office is 10x better than it was when I first bought my home.

Most of the time If I find myself leaving the house during the day it’s to do something simple like grocery shopping or getting a haircut, otherwise I’m home quite a bit. The neighbors driveways are all empty during the day while everyone is out at their day jobs. It really hits you when you also realize no one is really around during the day because everyone is working. It’s not like I can call up a buddy to just hangout with or even play some casual video games over the internet because everyone is at work.

My girlfriend Brenda also works from 6am-2:30pm so most days she is back home fairly quickly and we spend time together at night so it does not feel like I’m really ‘home alone’ the entire day.


Ahh.. what a fun subject. In 2016 I was working a full time job up through August while doing all my online projects in my free time, mostly for 2-3 hours a night combined with work on the weekends. I specifically saved a ton of money knowing I’d get hit hard with taxes and I most definitely did. I ended up owing quite a bit more than I had hoped but at the same time I knew it was coming and was 100% planned for it.

One suggestion I’d make would be to look into Painless 1099 as a solution, I signed up and even spoke with the owner but I have not started utilizing it a whole lot. I’m currently just using the general rule of thumb that 30% of everything I make should be set aside so I’m not going crazy with my spending habits.

Dress Code

Some days I’ve found myself feeling entirely lazy to the point that I wear pajamas all day and won’t leave the house at all, about 90% of the time I’ll dress as if I was going to a day job so that way if I do for any reason end up leaving the house it’s just easier to get up and get going somewhere.

There are also days where I actually completely dress up, wearing a nice sport jacket mostly for the purpose of doing video recording for my online courses. I generally feel a lot more confident when I dress better and it motivates me to work on producing video content for my courses as well.


Right now I typically keep track of everything I’m working on in a tool called Nozbe, I absolutely love it and it’s a simple way to keep my to-do lists synced across my desktop and cell phone. I have a repeating task list for doing chores around the house and I generally use Nozbe every time I need to make a note of something I know I need to get done just so I simply don’t forget about it.

I also made a pretty in-depth post on all the tools I use in my business, you can check that out here.

Wasted Time

Something I’ve found myself running into quite often is jumping into opportunities to chat with people either over Skype, Facebook chat (thank god I block my newsfeed at least) and even on phone calls. This in many cases has been a big time waster, phone calls ranging from casual chats to business related stuff.

Some days I think back and wonder “Where the hell did the day go?!” and realize I spent half my day getting getting distracted with random conversations that take me away from doing actual money earning activities.

This is something I need to get better about and really have more of a set schedule for these types of things.

Fear, Mindset and Partners

Fear is also something I’ve struggled with, believe it or not despite having quite a bit of money saved in the bank even after paying Uncle Sam I find myself thinking about the worse case scenario – Needing to go back to a day job. I’ve actually built up this absolute hate for working for others and building other people’s businesses. I probably would be the most terrible worker ever for this very reason. I worked day jobs for the past 5+ years all the while doing everything in my power to generate additional income online so I could quit.

It would feel like a massive defeat to have to go back to an office job at this point. Of course I know it’s not the worse thing in the world (pretty much 99% of people do this everyday) I just can’t stand it anymore and that’s why I continued to build my own assets and work on Sundays for several years straight so I could escape from being an ’employee’.

I sometimes have to remind myself that I have a lot of skills and knowledge of how to make a living online, I’ve had a lot success doing all kinds of different things. If it really came down to a point where I’m down to something like 10k saved and things are nearing ‘critical’ I’d likely go to UpWork and simply apply to 10-20 jobs a day and bust my ass trying to land freelance work.

Right now I’m utilizing UpWork for ‘some work’ but not making it a full time effort where as I could be putting more time into Evolutly and lead generation during the day.

One thing that I’ve also had a really tough time with is feeling like I’m relying on others to have success in some cases. I’ve had many partnerships that completely failed or were just simply temporary product launches that made me a lot of money all at once.

I partnered up with Paul James shortly after going self employed and by far it’s been the best partnership I’ve had in all my years of online marketing. The scary thing about self employment is that I’ve had to get used to the fact that over a span of sometimes a month or 2 my income could be very minimal and then I do something big that earns me a lot of money such as a product launch.

We have:

-Launched 3 products on WarriorPlus (2 of which got deal of the day)

-Done countless webinars together now with our own following for various courses and online products (sold well over $20,000 on webinars)

-Launched a SaaS software together called Evolutly which has so far earned us over $12,000

I’d like to keep this partnership going for sure as it’s worked out pretty well for the both of us. We are mostly looking to continue putting our focus into Evolutly and selling our courses with a 50/50 partnership.

Focus & Discipline

I decided to pickup the Mastery Journal by John Lee Dumas which is a 100 day plan to basically help you stay more disciplined and focused. I used it on and off for about 2 weeks but managed to fall out of a habit of writing down my goals for each day. This is something I definitely want to pick back up again and I can see why it’s helped John become so successful online.

I’ve had my fair share of distractions these past 8 months, there is always some marketing some “awesome new shiny object” which could be a software tool, a course or anything related to this. I’ve gone back in my head multiple times over to my long story article I wrote right when I went self employed.

I want to spend time on the things that I’m passionate about but I also realize that what I’m working on needs to generate money for me to continue paying the bills. It’s so easy to see all of these opportunities come my way and want to go down a different path. This has been one of the hardest things for me to deal with and it always has been one of my biggest challenges in the online marketing space.

It’s a good thing I am VERY optimistic about everything I do, the problem with this is every time I see a new ‘shiny object‘ opportunity I get excited thinking “this is the answer“. As much as I still personally struggle with focus I’ve realized that nothing happens overnight in the online marketing world.

I don’t care what anyone says, there is no ‘magic bullet’ or instant way to see success online. It all comes down to simply taking action and consistently doing that same work over and over again to have success.

For everything that I’ve done that has worked for me it’s simply come down to just putting a lot of time into something and working on it until I have success with it. The biggest examples of this for me would be teaching online (39 courses on Udemy and over 100 now on Skillshare) and I’ve also started tackling UpWork quite a bit which I’ve now earned over $10,000 on.

I’m still ultimately trying to figure out what it is I really want to do, even after 8 months you would think I’d have it figured out 100% but everytime I think to myself.. Will I still be doing this 1 year from now? 2 years from now? I debate over it in my mind.

Right now my biggest goals are growing my brand new SaaS application Evolutly and generating leads which I could use to sell my online courses. I’m 100% sharing exactly how I land SEO clients with Upwork over in my free 4 part video course. (This is how I’m building my email list right now).

As we move into the month of May my ultimate goal this month is to really buckle down and really FOCUS on Evolutly. 

I’ve been reading Will It Fly by Pat Flynn and so far I really feel as though I’m onto something that has already shown us signs of success without even tapping into it’s potential market yet. 

I also spent the better part of tonight going through my email and archiving a ton of folders while also utilizing unroll.me to get rid of lots of unwanted email subscriptions.

I’m setting myself up to go into my week’s more and more with a successful positive mindset.

-Working out every week

-Trying to eat better, healthier foods

-Staying well groomed and not getting lazy about dress code, you know the basics like a haircut, shaving etc.

-Keeping my environment clean as much as possible, just overall keeping the house clean.

Thanks for reading and I’ll surely update this post as I learn more moving through 2017.

About the Author

I'm John, I'm just an honest entrepreneur here to speak the truth about internet marketing.

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