One of the so-called “advantages” of working for the man is that it yields a predictable income month in and month out. Whereas working for yourself there’s no predictability.

This leads many to think that entrepreneurship is in fact then somehow riskier.

However, in my opinion the opposite is true.

It’s the same principle as diversifying your investments to spread out risk.

If you’re just getting one paycheck, what happens if you get laid off? But when you get your income from multiple sources, you can get laid off, and still have some income coming in.

That was the case for me this month, but I still made it through.

After a record breaking $52k May, my income took a massive hit after the loss of 2 of my major “core” accounts, and conclusion of a large shorter term project.

This month’s total certainly proved that as income can fluctuate quite a bit as it was down by roughly $33,000 (!)

Here’s how the numbers played out for me in the month of May:

  • Upwork/ Online Freelance: $18,200
  • Fiverr: $947.52
  • Stock Dividends: $22.69
  • Cash Interest: $131.67

Total income received in the month of April: $19,301.88

Overall, a large hit to my income this month, but still overall not bad, as this would equate to approximately a $233,622 yearly salary, a little below my desired total for the first year off work freelancing online full-time.

Here’s what how it all went down this month:

Upwork/ Online Freelance

As mentioned, I lost 2 major accounts – what I call “core” accounts.

Core accounts I think are critical to your success as a freelancer. They are what allowed me to originally feel confident enough to leave my day job.

To my way of thinking, there’s 2 types of freelancing accounts – short term jobs, and long term clients. Long term clients who you have on retainer, or have an agreed upon hourly amount per month, form the backbone of your business. They’re what allow you to have the freedom to work for yourself. Then the short term jobs add color & context to what you do – these are one time projects. For me so far, what’s worked best is having about 3 core accounts and then landing a steady stream of short term engagements.

This month I lost a $5-$7k/ monthly core retainer with a software client. They hired a new CMO who the proceeded to clean house – he fired the internal marketing team, the vendors, and then moved over to some marketing automation software and other vendors whom he had worked with previously. In a case like that, there’s nothing you can really do, except thank them for the experience and move on.

I also took another hit by losing another client who just decided to move in another direction.

Finally, I had a large $18k project last month that was a one time project, so that income loss was just due to that project being done.

Next month I’ll have to step up my new business game & try to rebuild to stay on track. On a positive note, the extra time is giving me some extra time to work on things I’ve been wanting to do, like starting this blog, so for me I’m questioning if I want back into the sanity of April, just to make a larger paycheck.


A decrease from April and now a portion of this is going to additional expenses as I hired someone to essentially run the day-to-day of the Fiverr business, communicate with clients, and fulfill orders. My time spent there now is rather minimal, so the income that does come in is pretty much passive for the most part.  Additionally we had a slight decrease in order volume last month, which again is somewhat outside my control, as Fiverr controls who gets impressions, and who doesn’t. Fortunately a number of my gigs have good rankings, so we get a steady flow of traffic. In any case, my Fiverr partner & I are working on building this business up, and actually start promoting it (which we’ve never done – it’s all been just passive traffic), so I hope to see this Fiverr number go up in the months to come.

Stock Dividends

This isn’t a big income source for me currently, and I aim to transform it into my largest source over time.

Cash Interest

This is the only area that went up for me as I increased my cash holdings over this time period.

Currently I bank at Capital One 360 and Spark, both of which sport stellar (at the time of this writing) 1% yields. If you have cash or are building an emergency fund, I would highly recommend these guys.


Online Income - May 2016


Overall, not my worst month, but certainly down significantly from the first quarter.

As mentioned, one of my goals is to reach $250,000 in purely online, virtual income. With this month’s $19,301.88 income, that puts me at $133,994.97 for the year, or 53.5% towards my goal, still ahead of schedule.

I’m really enjoying these checkups as they are both motivating for me, and hopefully should serve over time as a good indicator of longer term trends and my success (or lack thereof) as I progress.

I’ll update my monthly income report to reflect this most recent income.