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It’s easier than you think

Thanks to what I do as a career advisor, I’m always talking with people who are frustrated with their jobs, and even their lives. We like to think that we can completely separate work from our personal identity and life, but we’re kidding ourselves. If you have a bad day at work, it tends to follow you home. If you’re having trouble at home, it shows up in how you work and interact with your colleagues.

I often discover that this frustration in life happens when people feel stuck. If work is going well and your career is advancing nicely, you don’t tend to question things. The questions only arise and the frustration sets in when you hit a ceiling, feel stalled in your career, or you don’t see a clear path forward.

After a few years of repeating this pattern, jumping from company to company only to inevitably face the same frustrations again and again, some people start wondering if they should break free of the 9–5 grind and start their own business (I know that I finally snapped).

Take everything you know and love doing, and flow that into a new business. Leave everything behind that you hate about your job. Carefully craft your new entrepreneurial career to eliminate all of the things that you found frustrating in your old gig.


Easier said than done?

Sounds great! The only problem? You have no idea what kind of business you want to create.

First, it seems overwhelming. There are more than 28M small businesses in America alone (125M globally) and the North American Industry Classification System has over 500 pages of business classifications. There are so many business structures and types of businesses that you could start that you don’t even know where to begin. How do you focus? How do you choose one idea in which to invest your precious time, energy, and money?

Second, some people think they have nothing that they could offer as a business. They are accustomed to being an employee, deeply specialized, and being pigeonholed into a specific role. With those blinders on, they can’t really imagine being independent, or having customers or clients willing to pay them for something. It just isn’t clear what they have to offer. They really are interested in starting a business, but they fear that their only path is to go back to being an employee for a similar company.


Here’s the good news

If you’ve been successfully working in the corporate world for a decade or two, you absolutely do have something of value that people will want. If you’re feeling overwhelmed, it helps to focus on where you’ve developed your deepest expertise.

I’m going to simplify things. If you want to scratch your entrepreneurial itch, I’ve observed that it really boils down to 3 types of businesses.

  1. Selling what you can do.
  2. Selling what you know.
  3. Selling who you’ve become.

What can you make or do?

I’ve found that this is one of the easiest businesses for a 9–5 employee to start. Why? Because it is based on what you already have several years of experience doing in your day-to-day job. You have either been providing a variety of services, creating some type of product, or maybe even a little of both.

Examples from my social circle:

  • An accountant who started providing business accounting and tax preparation services
  • A designer who founded her own design service consultancy
  • A software engineer who became an engineering contractor for hire, and then he started developing and selling his own software
  • A PR leader who left a corporate job to start her own business providing PR services on demand
  • A field service technician who began offering in-home HVAC repair services on his own
  • An in-house recruiter who spun out to become an independent headhunter

I know how quickly this type of business can be created. I have witnessed first-hand many of my friends in Silicon Valley Tech do exactly this over the past 20+ years. Some of have been independent for decades. Plus, this is what I did when I first left my comfortable 9–5 job lifestyle and became an entrepreneur in 1998.

I quit my job as a senior designer at a startup and formed a solopreneur “design agency” in less than a week. I had my first client before I even quit my job, and I added additional clients over the next few weeks. I basically sold what I could already “do.” I had been providing my software design “services” for years as a full-time employee at IBM, Apple Computer, and a couple of startups.

Whether you’ve realized this yet or not, you are a product and successfully managing your career is like running a “Business of You”. The value you create for your employer isn’t very different from the services a consultant would sell to your employer to replicate what you do.

A useful exercise is to transform your current detailed job description into a business plan. How would a business describe its services if it offered exactly what you do day-to-day? What would that business charge? If your employer hires contractors or consultants to provide similar services, what are they paid?

For me, the transition from employee to independent business owner was almost seamless. The service I provided was dialed in, and I had my Silicon Valley network to tap into for discovering new clients. I also formed deep friendships with a number of other independent consultants who were doing exactly the same thing in design, engineering, QA, and program management. We would often bring each other on for big projects.

Finding customers was fairly easy during the Dot-com Boom in Silicon Valley. As I would discover later, I was spoiled and didn’t learn about the importance of marketing, advertising, and lead generation until much later in my career. The only new and challenging part of running a business was the accounting and paperwork. I still don’t enjoy that, but it has now become much easier to outsource many aspects of your business that aren’t directly related to your core offering.

One of the drawbacks of a business that sells goods you create or services you provide is that it is an active revenue stream. It requires that you are involved, is limited by your time, and you are essentially selling your time for money. It can be scaled by hiring employees, or if the “goods” you create are digital goods (e.g., software). But, an interesting transition from this first type of business is to move on to selling what you know, vs. what you can make or do.

What do you know?

If you’ve been in the working world for a number of years, you have acquired a great deal of knowledge, skills, and experience. This “Toolbox of You” can be packaged up and sold as books, courses, training services, workshops, and more.

Photo by Marcos Luiz on Unsplash

Unlike the first type of business, which is typically considered “active,” this business can generate both active and passive income streams. “Passive income” is a bit of a misnomer. It does require a great deal of active work to capture the information and put the system in place that will generate the passive revenue later.

Selling what you know takes you into the world of consulting, vs. feeling like a contractor when you sell what you can make or do. It also feels really good to be able to help someone with your hard-earned experience and knowledge.

There are a number of options for providing your knowledge live in training sessions, workshops, and speaking engagements. But, you can also capture your knowledge and offer it in a course format that can be sold essentially forever, without your active engagement. This has become easier than ever before with services such as UdemyThinkificSkillshareTeachable, a dozen others.

Selling your knowledge successfully does require that you’ve consistently demonstrated your expertise, can honestly back up your claims of experience, and have some solid social proof. Competition has really heated up in this space.

Thousands of people will claim that they have the same knowledge and experience that you do. You will need to stand out and set yourself apart with proof of your expertise (e.g., through writing and speaking), validated experience (Linkedin helps here), and testimonials and recommendations(which are invaluable when they are from other reputable people).

Who are you?

For this third type of business, you must have achieved a degree of visible and recognized success. I will admit that this is the hardest business to build of the three, and not everyone will be able to do it. It goes beyond what you can make or do, or even what you know. It is based on who you are, your career and life path, your notable success, and the resulting lifestyle you now enjoy.

Tim Ferriss from Flickr

Think Oprah, Tim Ferriss, Kimra Luna, Tony Robbins, and Tai Lopez. Their fans don’t just want to learn from them, they want to become them. They want to follow in their footsteps.

This type of business isn’t about hiring such people to create a good or provide a service. They are beyond that. This isn’t even really about paying to learn what they know. The implied sales pitch is more like this:

“Do you see my success? Do you want my lifestyle? Read my story. This is my rise from rags to riches. Attend my event, buy my book, and discover how you can follow in my footsteps to achieve my success and become the next  me.”

A real-world example

Ok, we’re not going to be the next Oprah. But, don’t get discouraged. This third business is actually achievable for folks like you and me. You will need to focus on your niche and find your 1,000 true fans, but it doesn’t have to happen overnight (which is a good thing, because it won’t happen overnight).

It’s a natural progression for people to take their business through phases from type one, to two, and then to three. They start out offering their services, then they start capturing their knowledge to sell as a course, and eventually they have enough success and fans that people will pay to learn how to follow in their footsteps.

I’ll use the example of a great photographer I know. I know someone who developed decades of experience in the industry, and she now has her own successful photography studio business. Over the past few years, I watched her take her business from what she could offer as photography services, to teaching courses leveraging her deep knowledge of photography, and eventually into the third type of business of how to become her: a successful business owner with a thriving studio.

Her first business/income stream

Products: She sells a client booking toolkit. 

Services: You can hire her photography services for weddings and family portraits.

As her second business began to take off, she dialed back this first business, which is essentially selling time for money. We all know that doesn’t scale well and has inherent limitations.

Her second business/income stream

Courses: She has courses on how to find new clients, secrets to great wedding photography, how to capture someone’s real personality in portrait photography, etc.

Now, as her third and more lucrative business began growing, she let the courses become a passive income stream that only requires occasional updates and tweaking.

Her third business/income stream

Selling her path: She has a premium offering to learn everything about following her path from start to finish of how she broke into the photography business, scaled it successfully, and now runs a profitable studio.

This may seem like a nuanced difference from the second category of “what you know.” The difference is that the focus isn’t just on acquiring some key bit of knowledge from her in a course here or there. Her followers desire to become the next “her.” I’ve referred to this a “career hero” before, and how much you should focus on what your hero actually does day in and day out (vs. focusing on what they have).

Transforming frustration into passion

I’ve spent about 13 years in corporations and startups, and another ~11 years running my own companies and businesses. I’m thankful for the people I met, the lessons I learned, and the experience I gained. But, yes, working for someone else can be frustrating. Most of us don’t have great bosses, and that is one of the biggest determinants of our happiness and satisfaction.

The longer you work in a specific type of role and for a specific type of company, the harder it is to imagine doing anything else. You may have even forgotten what it is that you wanted to do with your life in the first place. You may be tempted to break free and start your own thing, but feel stuck, overwhelmed, and at a loss for what “your thing” is.

I hope this article helps you see that you do have options. Of course you should always strive to improve your job and make it work for you. Of course you can always look for a better job at a different company.

But now, I hope you understand that you could also wrap up your amazing talent, skills, knowledge, and experience and create a lucrative business from that package (more easily than you may have thought).

I wish you the best of luck! Feel free to reach out if you need any support, advice, or guidance.

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