How to Create Multiple Income Streams: 7 Ideas to Empower You

A week ago I got a question on Twitter that I couldn’t answer in a tweet, or a thread. I thought the question was advice on how to create multiple income streams, but when I reread the question this morning I realized it was a much harder, and wiser, question:

Writing a post on how to create multiple income streams is a fun task. Sharing how I actually created my multiple income streams… well, that is a review of some painful decisions, steps, missteps, accidents, and wins. It is an introspective look back through my journey. My journey has been long and painful, full of questioning myself and second-guessing decisions. It’s been a lonely journey filled with key relationships (sounds like a paradox, but it’s not).

My journey to multiple income streams started at a very young age. I’ve blogged a lot about the topic here, and even wrote a 16-tweet thread with tips here (here it is on my blog). I’ve written about multiple streams of income for years… you can find my blog posts over the years on this topic here. PLEASE READ THE THREAD FOR A QUICK TAKE ON MY TIPS ON HOW TO CREATE MULTIPLE INCOME STREAMS.

I want to say my journey to creating multiple streams of income started when I was young. Like most kids, I wanted to earn a buck where I could. I think my earliest serious venture was mowing lawns. I could make a whopping five dollars mowing a front a back yard. Doesn’t sound like much today but in the 80’s you could quickly earn enough to pay your way, with some friends, to go to the local pizza joint and get pizza, root beer, and play video games for a few hours.


how to create multiple income streams started when I was a kid

My older brother had a successful paper route and earned great tips over Christmas. I tried to follow in his footsteps but found a paper route to be super frustrating. Getting up really early sucked. Rolling the papers was tedious. Having to go door to door to collect monthly payment was lame. And worst of all, when Christmas came around, my tips were like 10% of what his tips where. I didn’t get it, and I quit.

Fast forward a decade, I was in Mexico and bought probably 20 or 30 cool necklaces with the intention of selling them to students at my university. When I got back to school I sold exactly zero necklaces. I learned that having an idea was one thing, executing on the idea was another. More specifically, I learned that I was not a transactional sales guy.

Fast forward a few more years… my wife and kids spent Christmas vacation at my parents’ house just two weeks before I was going to be laid off. I didn’t know I was going to be laid off but I certainly felt unrest at my work. The writing was on the wall but I was ignoring it. Anyway, I love going through my mom’s bookshelf. One night I found a book titled Multiple Streams of Income. I read half the book before I left for home, and was forever changed.

Alright, one more anecdote before I dive into my tips on how to create multiple income streams: My dad was a government worker. I learned that he could not have other jobs, or income streams, without declaring them and having them be approved. Something about “we know we don’t pay you enough to drive that super nice car… are you a spy??” I didn’t realize this was abnormal, so in my formative years my flawed understanding was that you could only have one job and that was it.

In 2006, during my Big Fat Failed Job Search, I was interviewing for a role I really wanted (and was sure I was going to receive an offer). I had already started JibberJobber and wasn’t ready to give that up, just because I was landing a job. I asked the interviewer if having JibberJobber on the side would be a problem. He looked at me a little confused and responded, “No problem at all. The manager across the hall has a catering business. The manager down the hall owns a movie theater,” and went on to give examples of a few others who had side hustles.

I was like,


Alright… so that’s my foundation. I dabbled in multiple income streams, although I didn’t realize this would be my long-term, professional mindset. I had experiences along the way that prepared me to not have a normal day job as my single income stream.

I know my journey is mine and yours is yours. You can’t duplicate what I’ve done. There are too many variables. These might work for you, they might not. The question was how I did it. I hope this helps you figure out your own seven tips.

How to Create Multiple Income Streams

#1: Fail at Your Most Important Income Stream

While I don’t consider myself a failure, I do think my first real, big job ended poorly. Very, very poorly. It was my only income stream. It was what I had planned on my whole life, I thought. I was devastated when I lost that job. That devastation impacted many decisions I made. It still has an impact on how I think about careers.

I needed to have an abrupt, negative end to my old career. Otherwise, I would have pushed through it. I was loyal and stubborn enough to try to work hard even though an environment was toxic and the road was just a big fat dead end. Getting let go helped me let go of the rigid plan I had created.

how to create multiple income streams even with dead ends

I like plans… don’t get me wrong. But my plan was not meant to be. I’m glad some people have great careers, make plenty of money, and stay with the same employer for decades. Bonus points if they are actually happy while doing it. That is awesome, and I rejoice with them! But for me, and many I’ve talked to, that’s not our reality.

I needed everything to be taken from me, career-wise, in order for me to recalibrate and get on the path I was meant to be on.

#2: Be Prepared to Make Hard Decisions

Hard decisions don’t always mean doing hard things. It might mean making a decision between Awesome Choice One and Awesome Choice Two. Before I started JibberJobber I had three business ideas I needed to decide on. I chose JibberJobber even though I had two others that could have been pretty awesome. It was hard to choose, but I had to.

how to create multiple income streams focus

I had to choose where to put my time, what to focus on, and what to leave for much later.

When you have a normal job you normally have well-defined job description. When you are creating your own income stream (or, starting a new business), YOU have to decide what is most important. This is either really freeing and exciting or it is overwhelming and frustrating.

But you chose it.

You’ll have a never-ending list of decisions to make. My invitation is to focus on the most important things, make progress where you need to, and let a lot of other things go.

#3: Brainstorm a Lot

In another blog post I talked about sitting down in seclusion and listing the revenue streams I was working on. I thought I had a few… I listed ten. TEN! Those ten ideas have evolved over the years. I’ve removed some, added others, and ended up with where I’m at today.

My point is to be intentionally open and thoughtful about what you choose to do.

I just spend the last three weeks working on a new income stream that I never, ever thought I’d be interested in. I had heard about it years ago and thought, NO WAY. But, the opportunity came along and everything seemed right. I could invest my time and resources into it, the market seemed to be at a good place, I’m in a good place in my life, and perhaps most important, I found the right partner to work with.

how to create multiple income streams find the right partner

Instead of waiting for ideas to come to you I want you to sit down and brainstorm. Think about all kinds of ideas or needs. Remove the “why not” and “what if it doesn’t work” ideas during the brainstorm phase. You can get into a more critical assessment later but in this phase, start with “what if it did work?”

Look, if you go work for a company you will be working under someone else’s brainstorm. A hundred years ago someone sat down and said, “what if I could create a better soap?” And then they got some chemicals in their bathtub, mixed them together, and here they are today with a multibillion-dollar organization (this, by the way, was the story of a vendor I worked with a few years back).

Someone’s got to brainstorm. I want you to be purposeful about it. Do it to start a revenue stream and continue to do it as you build your portfolio.

#4: Allow Other Income Streams to Organically Grow

Years ago I gave a presentation to a bunch of young entrepreneurs and I talked about a friend who’s son sold their chicken eggs. The kid got to keep all the money because he took care of the birds… fed and watered them, collected the eggs, worked with customers, etc. My friend figured this was a good learning experience for the kid.

At the same time, I had some peach trees in my backyard I wanted to make sure where producing at their max. I talked to another friend who grew up on a peach farm and he said the best fertilizer for fruit trees was chicken poop fertilizer. I immediately thought that my friend, who’s son was making a few bucks a day selling eggs, could easily create a chicken fertilizer business and have his kid make a lot more without having to invest in more product (or, goods sold).

They were literally walking on top of what they could have been selling to neighbors for their fruit trees.

how to create multiple income streams fruit trees

I called this poop idea residual products/services. What are residual products or services you could offer?

Another example: I live in an area where we have basements, and basements have window well and windows. I hate cleaning mine out, even though storms will bring in tumbleweeds and other junk. So I begged my kids to go out and charge, say, $5 per window well (which means they could make $15 or $20 per house).

Then, we brainstormed residual services… like washing the windows, painting the window wells, spraying for weeds, replacing the rock, etc. A $15 house could easily turn into a $100 house, right?

Don’t get too focused on what you think you are doing/offering when there are other tangential, logical, organic ideas that grow out of your core offering.

#5: Learn When to Move Away From Something

This goes along with making hard decisions… but it might be one of the hardest decisions you have to make. I’ve had income streams come, thrive, and they die. Mostly, they died when it was the right time. For example, for a while I was an in-demand professional speaker. That was partly because I was one of a few people who had written a book about using LinkedIn. But then, one day I wake up and find there are dozens and dozens of authors who have books on LinkedIn.

I was no longer one of a few, I was one of many. And my conversations went from, “how much do you charge” to “will you speak just for a free lunch?”

how to create multiple income streams free lunch

My mortgage holder didn’t like the idea of me working just for a free lunch. That, along with COVID, became the end of me travelling a lot to speak in person. I still do it a little, and I do it online, but not nearly like that first year when my book came out. That was a magical time.

I was also a paid blogger for a company for a while. It was a great gig, really. I enjoyed it and got paid really well. Until my main contact decided it was time for me to stop… it wasn’t my choice, and it impacted my income, but I needed to move away. I hadn’t pursued paid blogging, and new that when that client went away I was done with that as an income stream. That was a decision I had made a long time before the end.

One thing I’ve learned is that you need to figure out how you’ll handle these situations. Will you need to get another income stream, nurse an existing income stream, or just go back to your primary stream and focus more on that?

I can’t answer that for you… again, many variables. But please, please prepare to lose one, ore more, income streams.

#6: Just Keep Working at It

If you would have asked me 20 years ago how to create multiple income streams I might have either given you some low-hanging fruit ideas, or I would have said I had no idea (because I was pretty focused on my job goals).

If you would have asked me 10 years ago how to create multiple income streams I would have given you better advice, based on the path I was on, but the truth is, your path should have been different than my path. I had to believe in myself, or a system, or hope, or whatever when no one around me did (to be fair, my wife has been extremely supportive).

You have to just keep working at it when you don’t understand what’s happening, or when you aren’t sure if the right things you are doing will actually pay off.

This makes me think about the cartoon drawing of a person with a pick axe, underground, digging a tunnel hoping to find gems. They give up just inches away from the gems. They put a ton of work in but they didn’t put enough work in to get to the gems.

Being an entrepreneur feels a lot like that. Lonely, tiring, hard work, and nothing in front of you but a rock wall. What if you had equipment to help you find gems? What if you had better tools, or a better team?

Sometimes you just have to keep working at it with what you have.

Bonus: Sometimes you have to make those hard decisions to pivot. This doesn’t mean you are a failure, though. It just means you made a risky and educated decision to change direction.

how to create multiple income streams don't panic

One day someone is going to ask you how to create multiple income streams and you’re going to scratch your head and think, “well, I did it this way, but your journey should look completely different.”

If you want it bad enough, though, you’ll keep working at it, even if the “it” changes along the way.

#7: Always Look for Non-distracting (or Complementary) Income Streams to Add

One of the things that worried me along the way was this: was I adding new income streams that would be a distraction to existing streams that I cared about?

Once you open your eyes to opportunity, and make space to pursue it, you’ll find it. It will pop up regularly. So what should you pursue, and what opportunities should you leave for others?

The way I thought about this was that anything I agreed to take on had to complement what I was already working towards. Writing my book on LinkedIn was just fine because that was a value-add to my audience of job seekers (JibberJobber). Speaking professional was great money, and it put me in front of a lot of people who should have become JibberJobber users (as well as spread the JibberJobber brand throughout my travels).

Working on a website for a real estate agent, though, would have been a distraction.

Creating my Pluralsight courses was a great complement to my work and a value-add to my users.

When big opportunities came I considered them based on how complementary they were, or how distracting they would be.

how to create multiple income streams watch out for distractions

I have other streams that are outside of JibberJobber… for example, we moved from a house that for some weird reason wouldn’t sell. We ended up renting it out and it has been a great income stream for many years. While I always wanted a rental I wasn’t prepared to buy one. This just happened because of some weird set of circumstances. So, sometimes you’ll find something dropped on your lap that just makes sense to keep or pursue. That can be okay, just be purposeful about it, always thinking about your limited resources and how thin you can be stretched.