My first year in business

I’m sitting here staring at the calendar wondering where the past year went. Seriously, I might have fallen asleep for a long period of time and am just waking up. Either way, I’m excited to share that I passed my one year self-employment mark. It was actually on 11/6, but since I don’t publish on the weekends, here we are. I’m cool with it being a day late, but certainly isn’t a dollar short!

If you didn’t know what happened, you can check it out here. To make a long story short, I left the company I had been working with for the past 8.5 years. I loved my coworkers, my boss, and the company, but I felt stagnant. I got pushed back into a position I didn’t want after my previous manager was canned. I didn’t think the company valued my skills of producing productivity-saving applications for my coworkers. It’s OK though, I’m getting the last laugh. Either way, I put in my notice in October of 2015 and had my exit planned.

You see, for so long I had been running a business on the side helping other bloggers with technical issues. My company, iMark Interactive, is there for WordPress bloggers needing help, but we also do stuff outside of WordPress as well. The business grew from just starting a blog and connecting with other bloggers. If you want to start a blog, check out this guide.

There was no conflict of interest between myself and my full-time job, so I kept it going. Near the end of my full-time tenure, I had grown my business to surpass my day job income. That was a good feeling because I’m a planner and need to know details before I make any big changes. So, quitting my job was really tough on me.

Arguing With Myself

I’ll be completely honest here. It took months to psych myself into quitting my job. It’s not that I was leaving a company I hated. I just didn’t feel anymore potential there. I love my coworkers. I’d consider them all friends and I still keep in touch with many. For the last 6 months at my old job, I used to walk around the office park thinking through my exit plan. I knew I had enough money to do it, but I had never really been self-employed before.

Yes, I did run an online electronics company before, but I still had a job when I did it. I still had something to fall back on if the business failed (it technically didn’t, but I shut it down). My new business needed my 100% attention and focus. If I were to succeed, I’d have to be there working toward my goals. I couldn’t give any attention to my full time job. Yet, I still found myself arguing to figure out if it were the best plan for me. My heart knew what it wanted to do, but my brain was still in planner mode. What were my contingency plans? What would happen if the business didn’t make it? What this and what that?

After some time, I realized I was just arguing with myself in a circle. If I could figure out the worst “what ifs” and be OK with them, then why not just do it? I knew if I were to grow the business any more than I already had, I needed to leave and go out on my own. It didn’t truly click in my head until my wife said this:

“Why do you work so hard at your business if you’re not going to go full-time?”

and my Dad said this:

“Son, you can either be an entrepreneur or you can work for one!”

These two quotes propelled me into jumping ship and going self-employed and you know what? I couldn’t be happier!

What I Love About Working For Myself

Many people ask me about the idea of working for themselves. It’s a scary thing when you’re in a job that has provided for your family for so long and then you drop out and go into something that has no guarantees or steady income. Self-employment can be scary, but also very rewarding.

There are a few things I love about working for myself and I’m going to lay them out here.

  1. My boss is awesome! Yes, I’m my own boss, but my annual review is going to be great this year. Who knows, I could get a raise. I really like I don’t have to ask anyone for permission to do something in my business. If I feel it’s a good fit, I just do it. That’s a really powerful thing.
  2. I work when I want to. OK, let’s get real, I work all the time, but that’s because I love my job. One of the sweet things about working for yourself is you can choose your hours and accomplish things when you can and have time. You don’t get that freedom “working for the man!”
  3. I can work from anywhere. This is really dependent on your business, but mine is 100% online based. If I have internet, I can get things done. I’m really excited about heading off to England in 2017 to work there for a number of weeks while we travel. No PTO and no need to ask for time off. I just do it.
  4. I make the decisions. Kind of similar to how awesome my boss is. 🙂  My business is here to help me achieve goals, not the goals of someone else. I get to decide the direction of my business, my pricing, my plans, and the customers I serve. This can also be really scary if you’re easily overwhelmed with information.
  5. I get to show off my skills. This is probably one of the best reasons. While you might work at a job you enjoy, is it taking advantage of all your skills? My business is a direct translation of my skill set. I created based on what I was really good at and it shows when I help people every day with their websites. I get to maximize all of my desired skill sets.
  6. My work provides for my family. This is also a great reason (if you have a family). While my old job provided for the family as well, this one provides even more. I get to take everything I earn and put it toward my family. The direct result of my drive and hustle goes right into putting food on the table and keeping a roof over our heads. This aspect can also be very scary!
  7. I can walk away at any time during the day. I love this one as flexibility is really important for me. I don’t like being chained to a desk all day long with no where to go. It’s why I went out for walks many times during the day. While my old job didn’t chain us to anything and was pretty flexible, I was expected to be at work for 40 hours (really much more though) a week and get my work done. Now, if I’m feeling restless and need to do something else, I just do it. No need to ask anyone or clock out.
  8. I can take days off without asking. This is the part of self-employment you hear about and wish for. If someone needs my help with anything, I can do it. I don’t have to get coverage, ask my boss, or anything else. I just do it. Yes, I still have work to do, but my business is run at any time day or night.

So, there are seven reasons why I love working for myself. There are probably more than this, but it’s all I could think about right now. Being self-employed does have challenges, which I will discuss next, but overall, it’s been pretty awesome!

Self-Employment Isn’t All Rainbows and Unicorns

OK, now for the stuff that brings many back to reality. The defensive pessimist in me will tell you that self-employment is not for everyone. Really, it’s not. There is a growing trend out there trying to get people to start their own businesses and become their own boss. While I think that is a great trend, I also know and believe that self-employment is not for everyone. Not everyone has what it takes to be a real business owner and entrepreneur. It takes a specific mindset to accomplish being a good business owner. If you’re a bad one, then you won’t make it long. It’s cut-throat in the business world and you’re responsible for your own actions. Let’s chat about what I don’t like about being self-employed.

  1. Income is variable. This is a big one for many. You don’t get a paycheck every two weeks or once a month when you’re self-employed. You get paid when you sell or provide a service to people. One month could be awesome and the next could suck so much. You really need to know how to budget with variable income when being a business owner. Nothing is consistent.
  2. Your benefits package probably sucks! If you have a spouse that still works and you can piggy-back on their health insurance plan and benefits package, then do it. Let me tell you, paying for health insurance for yourself is brutal. Obamacare officially sucks so much out of our monthly budget, it’s not even funny. The sad thing is the same Obamacare is what allowed me to become self-employed due to being a type 1 diabetic. Before, I wouldn’t have been able to qualify for insurance, but now I can. Unfortunately, it’s more than our mortgage by quite a bit each month. Killer! On top of health insurance, I have to make sure I’m saving for retirement. It’s too important to miss out.
  3. I have to make all the decisions. Yeah, I said this was a reason I liked, but it can also be a downer. When you have to make all the decisions, the buck stops with you. You’re responsible for making the right decisions and it hurts you even more when you don’t. That’s a lot of pressure day in and day out. It takes a special someone to get through this.
  4. You play every role. Oh, by far the worst part about being self-employed. Until you have the money to pay people to take over things, you’re the one that has to do everything. You’re the CEO, marketing department, customer service, tech support (unless you hire me for your website), accountant, billing and collections department, and every thing else it takes to run the business. You can easily get overwhelmed with all that needs to be done.
  5. There is no 40 hour week. There is a quote floating around that entrepreneurs are the only ones who will leave a 40-hour work week working for someone else to go into a 80-hour week working for themselves. Being self-employed makes it a little harder to run just 40 hours. You don’t just clock in and clock out. You have bills to pay and mouths to feed. If you need to near more, you work more.

There are more to list, but I figured one of the biggest downfalls of being self-employed is the constant ups and downs you face each day. While I can write about it, I figured I would use a graphic that puts it perfectly into perspective. This was created by Derek Halpern from Social Triggers and Zippy Courses. I hope you enjoy!

The day in the life of an entrepreneur

This literally is like my life every day. Did I make a right decision? Why did I do that? Oh, this is awesome! It just goes on and on like that every day. If you can’t handle these types of ups and downs, don’t get in business for yourself. You’ll lose all your hair!

So, How’d I do?

You’re probably wondering how the first year of being self-employed went, right? Well, I can answer that in two words:


This past year defied all expectations I had set for myself. I blew out my revenue expectations (hopefully I can do it again this upcoming year). While I don’t release revenue numbers, I easily crossed into six figures. I built a company I’m very proud of.  The best part about this year is I created a reputation for myself and my brand that I’m every happy about. I pride myself on my customer service and the value I provide to customers. I never thought that offering so much advice for free really would have helped me in such a way, but it really has. Yes, I built this company on helping people and giving information away for free. It can be done and I’m the proof.

As for what I think is next this upcoming year, I don’t have much of a clue. I’ve transformed my service offering this past year and focused on some things that can add more revenue to the business, but many of these things don’t pane out or take a number of months to actually be reflected. I’m still passionate about this business, what I’m doing, and where it’s heading. I just can’t wait to get there!

So, there you  have it. I’m one year into self-employment and it’s just the beginning. I got to a mark I wanted to hit and I did it with relative success. Here’s to the next year and to the five after that.

Are you self-employed or thinking about jumping into it? Let me know your thoughts in the comment section below!

I quit my job to run my own business

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  1. Even though I have to pay for my own health insurance (my bfs plan doesn’t recognize domestic partners ;( ) and pay taxes out the nose, plus take care of all my own retirement planning, I wouldn’t trade self employment for anything!

    1. I hear you there. The health insurance is a stinger right now. Doesn’t cover a damn thing and costs you an outrageous amount. Oh well, it’s the life we choose.

  2. Congrats on the great first year of being out on your own man! I think about it almost everyday to be able to finally quit my day job. Im still a few years away though I think.

    Keep up the great work and love your enthusiasm!

  3. Glad that it seems your previous experience has greatly helped with your blog, Grayson. Congrats that you made the right decision to be self-employed.

  4. So impressed. It’s really brave of you to go it solo. Good for you. I know for myself I earn extra money on the side. The amounts vary month to month and although I don’t depend on it, I find it a bit of an emotional rollercoaster waiting and wondering where the next earning will come from. Can only imagine that feeling is 100 times worse if you’re full time self employed!

    1. I appreciate it and yes, it’s a very emotional roller coaster to say the least. You always have to be on in order to make sure you make enough to cover all your costs, plus insurance, benefits, and anything else. It can be stressful.

  5. Congrats on your self-employment. Starting from April, I will be self-employed too. Takes some courage but hey, ain’t that what life is all about?

    All the best

  6. Congrats on the first year! I wish I could do that. I am sure you worked hard for this, but it did pay off.

    Keep up the great work! Hope to be in your shoes one day 🙂


  7. I had my own biz for 12 years and it was the worst financial decision I ever made. There were lots of great pros to the situation that for a period of time help me reconcile the fact that I torpedoed my income. My problem was a result of many small decisions that led me into a hole I couldn’t climb out of. I now work for the government and while the place can drive me insane there are also pros to that situation.
    My main problems were:
    1) not getting paid. I have bad debt worth a years salary
    2) doing something (taxes) that had a definite deadline I was up against every year
    3) caring more about people problems than they cared themselves
    4) abusing the flexibility of the schedule which resulted in too many nights and weekends
    5) doing something that required being accountable to a governing body (I’m a CPA), a privilege I get to pay for.
    Looking back I see a lot of things I would have done differently but for me, selling the business (which was a whole separate nightmare) and taking a job with the government was the best thing I did.
    There are “seasons” to life and your career follows those seasons. The hardest part is knowing when the season has changed and making the moves to change too.

  8. Paying for health insurance was my wake up call. It was already too expensive from the beginning but then it keep increasing. It’s a joke.