Total Reading Time: 8 minutes.
Good lord almighty, have I made some mistakes. This isn’t easy to admit or share publicly. As I write this, I’m telling myself to imagine this is just a private journaling session and will forever stay locked up — never to be shared with anyone, anywhere.
My hopes are that by being completely honest, raw, and unadulterated I can save you countless hours of headache and stress. Sometimes a simple mistake or defeat can seem like the end of the world. No matter how hard you try to play the optimism game, your reason will attempt to overpower all hope.
It takes time to see that your mistakes were just training. In fact, your mistakes and defeats are what make it possible to experience (and enjoy) success one day. Even now, I make mistakes, daily. The little ones still upset me, and the bigger ones can torment me. I’m sure you know what I mean, and have experienced the same feeling.
At times, it’s just not possible to do it right the first time. Experience is necessary. Nonetheless, there are many mistakes that can be avoided. These mistakes are not tactical or strategical, but educational — mistakes that lack wisdom.
As a solopreneur, it’s your job to educate yourself. No one else is going to tell you what to do.
This realization is both inspiring and heavy. This leaves me with a responsibility to make good decisions, get relevant and actionable advice from mentors, and study like a madman.
With that said, below are the 7 biggest mistakes I’ve made as a solopreneur.

1. Unnecessary Overhead/Expenses

One of the first big decisions I made when I became a solopreneur was to get an office space. Well, actually, a new friend at a conference offered the space to me. He said he’d only charge me $100 a month for the desk. In San Francisco, that’s quite a steal, so I took it.
Looking back, I think this is a big mistake. An office space is a luxury, and often an unnecessary expense for a new entrepreneur. In the beginning I didn’t look at it that way, but now I know better. $100 can be invested in the business (here are 15 business ideas) and go toward generating more revenue (e.g., through Facebook ads).
Even better, that money could be set aside for investing into new and existing assets, which could then put off more cash flow. Both of these concepts I didn’t understand before.
It didn’t stop there. I was the new entrepreneur, living the dream. If I wanted it and found a way to sell myself on its utility, I purchased it. Shiny new equipment, fancy software, and cool tools—all this is unnecessary overhead.
Looking back, my profit margins could have been higher from the beginning.
A top priority for every new entrepreneur should be to maximize cash flow.

2. Not Sacrificing

When I first left Google I felt an incredible sense of freedom, and I still do. For me, leaving the job world was symbolic, because I knew deep down that it was the beginning a new journey. I was ready to burn the bridges and go all in.
Yet, I didn’t sacrifice a whole lot. No massages? No nap pods? No billiards next to organic ice cream machines and table tennis next to refrigerators full of unlimited snacks? No problem.
I pretended (to myself) that everything was exactly the same. I continued enjoying the same activities, and living the same way, as if I was still making $120K.
This is a big mistake, but it’s not entirely about the money. The mistake is that I never sacrificed the way every solopreneur and entrepreneur must do in the beginning. I wanted to simply glide on over into this new world, and refused to sacrifice my lifestyle. I also didn’t sacrifice enough of my free time, and should have been more like the dedicated solopreneur I am now.
Looking back, it was right to enjoy my newfound freedom and flexibility. Yet, I should have sacrificed more of my social life. I should have said no more often. Great things happen in solitude, and that would have helped me feel more connected to my new craft.

3. Trying to Maintain Work/Life Balance

This mistake is a continuation of not sacrificing. One of the biggest mistakes I made was thinking I could keep the same hours and work 9 to 5 like before. Wrong.
I intend to build something that will leave a legacy. I intend to create valuable content and share information and lessons that can change people’s lives. That person lives and breathes their “work”, as I do now.
My mistake was naive, but forgivable. I tried to find balance, but couldn’t. It was a futile battle. I’m not advocating that you stay up all night and obsess over your venture. Knowing when and how to “turn off” is important. But to try and balance is difficult in the beginning, you’re better off just going all in.

4. Accepting the Wrong Advice

I was hungry for a strong start, and was willing to experiment with different projects, as long as they were relevant to my initial plans. The problem is, I was too hungry. I naively sought advice from the wrong people.
Why were they the wrong people? And how should I have known? One critical piece of criteria: they weren’t doing exactly what I wanted to do. I’ve learned to only get business advice from people that have done what I want to do (successfully), or are currently doing it.
It’s okay to get strategic or general advice. But I ended up pursuing an idea I believed in through a completely different method. This diluted my enthusiasm. I wasn’t proud of the work, because in the end it wasn’t uniquely mine.
Key lesson: always stay true to yourself and get advice from people that believe in you and your mission.

5. Researching/Testing Beforehand

Before becoming a solopreneur I didn’t know much about the world of online business. I’d read a book or two, and would browse a couple popular online business blogs, but that was about it. I know, shocking. Who does that? Me.
Not researching my industry/niche more was a big mistake. Not making my first dollar online before committing was an even bigger one. I committed to the idea of what I wanted to do without knowing what it would take.
This was both good and bad (ignorance can be bliss sometimes), because I took action anyway. If I did it all over again, I would definitely have set an initial goal to hit before making the leap.
Some examples: first 1,000 subscribers, first 10 customers, first $1,000, and so on.

6. Networking

For some really odd reason, I didn’t take the time to network with people much. This is abnormal, because most people would say I’m pretty good with…people. I love collaborating and sharing ideas with other humans, it’s where I get my energy.
I initially looked to my industry’s network and saw them as inspiration, not as a network. They were ahead of me, so at times there was a bit of envy to get there as fast as possible. At the same time, my social scene was too far “offline” (see mistake 3). I didn’t see the potential partnerships, friendships, and networking opportunities.
It’s important to network because you never know how you can help someone. All it takes is one idea or one perspective to change someone’s business. You also never know what friendships might arise, and that is invaluable as a solopreneur.
The people in your space will just “get it”. That understanding can’t be created with your other networks, so don’t take it for granted.
I take networking seriously now, and have dedicated time on my calendar for it. I recommend you do too.

7. Inconsistent Branding/Focus

It wasn’t until a year and a half into my journey that I realized I was making this mistake. It was a mentor that exposed the mistake to me. As soon as he pointed it out, it felt like a massive lightning storm of “aha moments” battering me all at once. It was painful, but also quite pleasurable.
The lesson summed up in one sentence:
Every single action you take in your business, whether it be creating a new YouTube video, attending an event, or writing a blog post, must always deliver on one single brand promise.
If the action or project does not deliver on your brand’s (yes, personal brand’s too) unique promise, then you are wasting your time. Furthermore, you are confusing your audience and customers with an inconsistent message.
As Larry Page, CEO of Google would say, you must have “laser focus” at all times. Prior to this epiphany I was spinning my wheels. I learned things I didn’t need to learn, and worked on unrelated projects. I was spread too thin.
Now, I know better. Since relaunching WILG in May of 2014 and making the brand my central platform, everything has changed. Exciting opportunities are coming in, our readership has exploded, and the brand has a consistent message. Plus, I’m able to focus completely on providing exceptional content to you.

Links to Resources

  1. The Lean Startup – Before you devote yourself to creating the most beautiful software or product in the world, learn about starting lean. Deliver the minimum viable product to your customers, and then iterate from there.
  2. The $100 Startup – It really doesn’t take much to get started. Read this book to learn how you can start your own solopreneur business for under $100. This site originally cost only around $100 to create.
  3. Regus – Hate working from home every day? Don’t get an office space. Get a Regus Businessworld membership. This will allow you to work from a business lounge (think fancy, quiet cafe) in almost any major city around the world, and even some small ones (2000 cities world wide). I use this around 1-3 times a week.

Mistakes can be painful. Some of them leave scars. But as with all mistakes, there is an equivalent benefit waiting in its shadows. You just have to be persistent enough to receive it.

What mistakes have you made in business or as a solopreneur? Which of my mistakes did you (hopefully) learn something new from?
Photo credit: MistakesCC License