Surviving My First Year of Business (Tough Times & Lessons Learned)

I quit my day job to give full-time blogging a try.

The past year and a half have been pretty shaky.

It’s been tough on Mrs. PT and I as we’ve dealt with the ups and downs of the self-employment journey.

I know many of you are going through similar scenarios and can relate. So today I thought I would take a moment to fill you in on how things have been going for me.

The Decision to Go Full-time

Quitting wasn’t easy.

At the time, my corporate job as an internal auditor and this blog were our only sources of income. A year earlier, Mrs. PT had left her teaching career to pursue her Master’s degree and be home with our little girl, which I really wanted her to do.

When I first started seriously hinting at the idea of leaving my career, it put Mrs. PT into a bit of a panic. She really wanted no part of me leaving the safe confines of a steady paycheck. She knew what kind of revenue my blog was generating at the time (not much), and she knew we would have to go out and buy individual health insurance.

We don’t necessarily have any conditions that would prevent us from getting insurance. It was just a scary unknown.

I had my own reservations. Would I be able to get affordable health insurance? Would my website revenue maintain it’s current trajectory? Would I be able to grow it enough to not have to dip into savings and to continue our financial progress? Would I be able to get another job if things didn’t work out?

In January, just one month before I eventually quit, I set a goal: even though I was tired of my corporate career, I would continue in my current job at least two more years and work harder than ever to bring my blog to a full-time level.

The two years would allow us to have another child, allow Mrs. PT to finish school, and allow for her to potentially get back to teaching.

Entrepreneur Dad and Daughter Baseball GameThis goal lasted a month. At work, I was assigned a three-week project in India that would have me miss our little girl’s first birthday. When it was just Mrs. PT and me, this job was the perfect fit. She would come along with me on these overseas trips and we got to see the world.

But now that we had a little one, the three-week trips were tough on our new family. The thought of this proposed three-week project was enough to help us make a decision. Mrs. PT told me that if I wanted to give blogging full-time a try, then she would support the move. It was on.

My next move was to bust through some of those fears I was having (i.e. health insurance, future job prospects, etc.). I quickly ran some quotes on The monthly premiums on the high-deductible plans weren’t that bad.

Today, instead of using health insurance found on the open market, I use a medical sharing program called Medi-Share. Medi-Share allowed me to reduce my monthly healthcare cost by over $700! Read my review of this life-changing service. Boy, do I wish it had been around when I first wrote this post!

Back to my story…We decided that if we cut back on some expenses, we could handle that.

Next, I took a look at the job market in my area for internal auditors and CPAs. Things weren’t ideal here in Texas, but they weren’t horrible either like in other parts of the Country. I was still getting the occasional call or email from a recruiter, and I felt confident that even if I had to take a much lower paying job, I could find a paycheck again if I needed it.

Additionally, my father runs a public accounting practice. As he has done many times over the years, he generously offered to allow me to do some tax-preparation work for him. So I knew I would have some extra money coming in from March to mid-April if I needed it.

With those two things out of the way, I was ready to quit. I gave my two week’s notice and wrapped up my projects there. Mrs. PT and I decided that we would use this time as an experiment. Let’s see if I can make the blog work as a full-time source of income and if it doesn’t work out by the Summer, I’ll start looking for work back in my old career with an employer that doesn’t require travel.

Lesson #1: Don’t let the supposed “monster under your bed” prevent you from getting up and doing something about it. Chase down your fears – don’t let them hang around – and see what you discover.

The 3 Month Experiment

For the next few months, I poured myself into making this work: I wrote two posts a day on the blog, I developed new revenue streams for the blog, I worked longer hours, I did a tax return a day for my Dad’s business. I loved it. There were no more “Mondays” in my life.

Truthfully though, I was working hard and not very smart when it came to the blog. I was doing some things right, but I wasn’t seeing big gains in revenue. It was a struggle to push things forward. Looking back, March to May is a tough time to grow a personal finance blog. That’s historically when traffic and thus, revenue (with the exception of tax-related stuff) starts taking a natural dip.

While the site was struggling to take off, I lucked up and landed a freelancing gig in late March. The folks at PerkStreet wanted to put their blog on the map and asked me for a bit of advice on working with personal finance bloggers.

I took the opportunity to pitch to them the idea of me being hired on as their blog manager. The gig would only require about 15 hours a week and I had the connections to make it work. The pitch worked. They generously hired me on to help manage their blog.

This would prove to play a pivotal role in us “making it” over through the Summer. While the PerkStreet gig provided a solid, baseline of income, I knew there were no guarantees (month-to-month contract). PerkStreet was a start-up company and I was an unproven blog manager.

I made another pivotal move in late April. After seeing slow progress with my site during the first two months of a full-time effort, I decided to bring in some help. I hired a consultant (you know him as Michael). I hired him to help to give my site some direction and to help manage one of my undeveloped revenue streams: affiliate marketing.

Like the freelancing gig, I had high hopes for this, but there we no guarantees when we started up in May.

Lesson #2: Do whatever it takes, including taking on additional side-hustles and looking for help when you’re progress slows.

Here’s my video with Matt Jabs of Debt Free Adventure covering some of this material. Sorry about the quality.

A Summer of Interviews and Baby News

Another month went by and not much progress with the site. Over Memorial Day weekend Mrs. PT and I had some talks and I made the decision to start looking for work. If things were going to continue on their current path, my revenue would not be enough to allow us to continue meeting our financial goals: retirement savings, another house down payment, etc.

I saw us having to possibly dip into our emergency savings towards the end of the year, or even quicker if the freelancing gig went away.

Additionally, Mrs. PT was ready to have another baby and move into a bigger house. Both things (“wants”, truly) would require a full-time job with group health insurance and a W-2, I thought. The “experiment” had seen some successes, but it had initially failed.

So I started looking for work. I figured I could get a corporate gig and still maintain the PerkStreet thing on a part-time basis. Since I now had the consultant helping with the site, PT Money would be able to get by, and even possibly still grow, on a part-time effort.

Over the next few months I sent out several resumes and went on several job interviews. I didn’t have much luck. I didn’t land that many second interviews and I struggled to explain the gap in my recent work history.

If I quit on my last employer, what confidence did they have that I would stick around for them? It’s a fair concern.

The next few months were bizarro world. The site traffic and revenue started to take off. I did the TV piece with Fox Business. The PerkStreet gig was hanging in there.

Things were looking up, but I was still this poor sap who couldn’t land a job. It was tough on me. I worried a lot during these months.

Then, we found out we were going to have another baby. I had to get a job now. Individual health insurance in Texas doesn’t cover maternity. I was nine months away from a $25,000 payout if I wasn’t on group health insurance by then. The news was shocking, but it was also freeing in a way. I had nine months. I decided to give the job search a rest, focus 100% on PT Money, and try to land a job later in the year, just in time for baby.

Lesson #3: Life comes at you fast and it’s hard to say where things, even your wants, will take you.

Self-Employment Success Isn’t Enough

August through December were some of the best months of my life. PT Money had become a financial success. Traffic and revenue saw huge increases each month. The strategy put in place by the consultant, along with the endless hours of work on my part was finally starting to pay off.

My revenue surpassed my old corporate career income. And for the first time in my life, I felt like a real entrepreneurial success. I loved my work and it was finally paying off.

But it wasn’t paying off to the tune of $25,000, the amount we would pay out-of-pocket for baby #2. So, as crazy as it sounds, I went back to sending out resumes in hopes of landing a job. I even entertained the idea of taking on a part-time job with benefits.

I still faced the same uphill battle with employers: the weird gap in my employment history. By late January of the next year, I still didn’t have a job.

Long story short, my parents once again came to the rescue. My father offered to bring me on with his practice and provide the group health insurance that we would need to help cover the maternity costs. I started with him in February, and on March 4th our second daughter was born.

Through April I continued doing “full-time” work for my father’s practice while maintaining PT Money, which continued solid growth.

After tax season, I returned to full-time blogging. Since that time, the site has seen some more ups and downs.

Google’s Panda Updates 1.0 and 2.0 (which I’m still struggling to recover from) have pushed the site back to last year’s levels.

I think had I not gone through such a volatile year last year, these last few months would have been really tough.

Lesson #4: Running a business never gets easy for long. You have to learn to love weathering the ups and downs that come with moving something forward.

When I look ahead, I feel confident about the long-term future of my business and about our ability to weather the storms.

I still love what I’m doing and wake up every day excited to take on new projects. It certainly helps that Mrs. PT and I are blessed to not have too much debt or too many monthly expenses to deal with.

So that’s where we’re at and that’s what it’s been like for us this past year.

Surviving My First Year of Business (Tough Times & Lessons Learned)

Avatar About Philip Taylor, CPA

Philip Taylor, aka "PT", is a CPA, blogger, podcaster, husband, and father of three. PT is also the founder and CEO of the personal finance industry conference and trade show, FinCon.

He created Part-Time Money® back in 2007 to share his advice on money, hold himself accountable (while paying off over $75k in debt), and to meet others passionate about moving toward financial independence.


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  1. Avatar Brian Satterlee says

    I have been on my own for 10 years now. It’s not always been easy. Good luck to you!