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Why I juggle 5 businesses at once

I started freelancing in 2007. By 2008, a month before my college graduation, I embarked on it full-time as a career.

The years 2008-2012 were roller coaster rides that would give anyone gray hair (or in my case, make me lose my hair). Clients came and went. Money rose and fell, as did stress.

Then, at the beginning of 2013, as my business was stumbling along on fumes, I was put on retainer by a big client.

Suddenly, I found myself with a steady paycheck (plus royalties!). My income stabilized. I got hefty quarterly payments in commissions for copy that I wrote. I even had enough time to grab the occasional one-off client here and there.

It was incredible.

After years of struggling, I had arrived. Life was great. For the next two years, my income soared. My wife and I paid off mounds of debt. We took little weekend getaways, just the two of us. We shopped and bought whatever we wanted because we were making such great financial progress.

Then came the phone call.

One Thursday in November

I was out of my home office, typing away in a coworking space in downtown Milwaukee. This was a regular practice for me, just to get my brain out of the house.

I emailed my retainer client a few questions about several active projects I had with them. My copy was still selling like gangbusters for the client, and they put a lot on my plate as a result.

My client replied back, asking for a phone call in the afternoon. Thinking nothing of it, I agreed.

That afternoon, I sat on one of the comfortable couches, put my feet up, and opened my laptop, expecting to take some call notes.

Instead, the client answered, “Hey Tom, it’s Katie from [CLIENT]. Just so you know, I’ve also got Melissa from HR on the call…”

My stomach sank. I knew what was coming.

“We’ve decided to terminate our working relationship at this time.”

No reason given.

No reason would have made sense, anyway. They were making back the money they were paying me in spades.

But they didn’t need to give me a reason. I am an independent contractor. They just have to tell me that they’re firing me.

My confidence took a body blow, but I wasn’t shaken up too badly. After all, I had worked with over a dozen companies in that industry in the previous few years. I had contacts! I would just go out and get another retainer deal, right?


It all disappeared

The regular pay was gone.

Clients weren’t really hiring consistently.

Everyone was moving to in-house copywriters.

I would bust my butt to deliver copy that clients would love. Then, they would tell me that the retainer agreement we were aiming for wasn’t an option anymore.

That happened repeatedly.

As the years progressed, my income kept falling… cutting half over and over again.

In 2014, I made great money.

In 2018, my income was literally 17% of what it was at its peak.

I don’t care who you are: losing 83% of your income is devastating. And we had two children in that time span.

We went from a comfortable living to hovering right around the poverty line for a family of four. It felt like, no matter what I did, no matter how hard I worked or who I schmoozed, I couldn’t catch a break.

I even interviewed at local agencies for copywriting jobs. I went through two rounds of interviews with one agency located downtown that worked on big, national brands. They even toured the building for me, showing me where my office would be.

And then they hired somebody else at the last second.

5 years of rebuilding

I did anything I could to pay the bills.

I started an online store selling cat socks (true story).

I bartended some nights.

I still grabbed the occasional copy client.

I started a wood shop.

I took up ghostwriting books.

Over time, I built up new contacts in the industry and kept massaging relationships that I had for years.

Then, in 2019, the ship began to stabilize.

Ghostwriting was paying well.

And my copy clients started coming back to me. In June of 2019, I was offered a retainer deal for the first time in years.

I didn’t stop hustling away, though

While ghostwriting wound up not being a long-term career for me, I kept hustling up clients and building relationships.

I kept selling stuff out of my wood shop.

Today, in 2021, I have 5 different streams of income:

  1. Copywriting
  2. Book publishing
  3. Coaching
  4. My wood shop
  5. Blogging (for myself and my clients)

Beneath these income streams are little sub-streams, further spreading out my risk.

For example, I blog for myself here on Medium and I also have clients who pay me to write blog posts.

I have 4-5 different copywriting clients, three of which keep me on retainer deals.

Is this overkill?


Each one of these income streams is a lever that I can pull. In some seasons, I pull harder on some than others.

Right now, copywriting is the main gig, and those income streams underneath the “copywriting” heading are doing well.

My wood shop, for example, is essentially on hiatus until lumber prices start coming down again.

And some are in the process of being built. I am trying to sell more books, and I am just building my coaching practice – teaching other copywriters how to build sustainable businesses without making the same mistakes I have in the past.

I’m making more money than I ever have in my life, but I keep trying to build new stuff on top of them.


It can all go away overnight

At the end of 2014, I learned that it just takes one or two bad pieces of luck to completely destroy your income and profitability.

I suspect that, in 2020, many others learned this same lesson.

I’ve chosen to work for myself, and that means I have to make sure I am diversifying my risk so that I am not reliant on one source of income.

If you work for yourself, you have to find the best way to do that, too. Maybe you just focus on taking on multiple clients. That’s not the way I want to go long-term, but that’s you. In any case, you need multiple streams of income.

Yes, there are weeks where I am so overwhelmed, I feel like I can’t breathe. I do have to juggle a lot.

But to me, it’s worth it if it means I have the peace of mind knowing I can weather storms that come around in the long run… while still providing for my growing family.

Image by Theodor Moise from Pixabay