Independence Is Simple, Not Easy

Reflections on the entrepreneurial journey

CISO Dreams… A conversation

At a networking event…

CISO: What do you do?

Me: I’m a Fractional CISO for Startups

CISO: Really? That’s so cool! I wish I could do that.

Me: Wait, what? I thought being CISO was the best thing?

CISO: Not really, depends on the company. Plus now with all the lawsuits and liability, it’s become quite stressful.

Me: But you all get paid top dollar right? Like 500k or even $1M+ annual take home. Not to mention benefits and stability.

CISO: Yeah, but it’s stressful and always an uphill battle. I’m burned out.

So this was a real conversation I had with a CISO last year. It was eye opening to be honest. I then ended up having similar conversations with CISO’s everywhere. 

What was going on? Why do CISO’s want to leave their cushy jobs and go out on their own? Is it money? Independence? “Control” of their life?

The life of an entrepreneur* is filled with chaos, especially in the beginning, but of course can be filled with reward. Not only that but the reward can be elusive if there isn’t enough thought into WHY you’re going on this endeavor. There will be low times where you question what you’re doing.

*The life of a solopreneur can be much more balanced, but still requires planning.

Being A Wedding Photographer

Let’s take a look at a different business: Photography.

You have this amazing passion for photography. You’re good at it and are able to capture excellent candid photos. A friend asks you to photograph their event and you do an amazing job. You get great feedback from everyone. 

“Best photos ever!”,  “You have a talent for this!”

So you decide to go into business doing event photography.

You then find out that to run an event photography business, 90% of it is NOT the photography itself. 

You find out it’s:

  • Scheduling and time management

  • Accounting, Billing, and Taxes

  • Customer Success and Satisfaction

  • Payroll and hiring staff

  • Negotiation and Contracting

  • Insurance and liability

  • Expenses (Equipment, travel, etc)

  • Maintaining cash flow (actually paying yourself)

These are the components of ANY business. Why would anyone want to go through all this headache? It’s way easier to work for someone else and collect a check every two weeks.

Here’s the key: You need a little bit of insanity and vision to go into business yourself. There will be low times that will require you to push through.

Now that’s the key to get INTO business.

The Path To Independence Is Different For Everyone

When any person or country decides to go out on their own, they are taking a big leap. They are selling themselves that we would rather be in control of our own destiny (to some degree, you can’t control everything), even though it’s going to take much more work.

FTE life doesn’t have to be so different. If you play your cards right, you are investing your extra income on real estate, the market, or whatever else. You are marketing yourself internally at the company to get a better salary or shares. You’re often taking a bet on this or that startup in the hopes that your shares and sweat equity will pay off. It’s the same thing.

However, being completely passive about your destiny regardless of whether you are a business owner or FTE will not get you far. That ship has sailed with our previous generation where they had pensions and a decent retirement.

A book I highly recommend is Design Your Life. It’s an excellent book for anyone at ANY stage of their life.

The Path Towards Independence Can Be Long

It takes patience, grit, and perseverance to become independent. The United States didn’t become independent overnight. 

It was a long journey with several steps along the way.

(Of course many details may be missing, so this is for illustrative purposes)

The Rewards Of Independence 

The reward can be very promising. As your skills and experience improve you increase your rates while at the same time your processes and efficiency are also improving. Whether it’s a wedding photographer business, business consultant, or cloud security person, this is generally true. The caveat, which also applies to FTE work, is that you must keep abreast of the market changes and ensure your skills are up to date and sharp. You must adapt.

Rewards don’t always have to translate into monetary rewards, although in the US there are tons of tax advantages catering to business owners. (except for health insurance that is!)

Here are some other typical rewards:

  • Flexibility in choosing your clients

  • Affecting change and results with your clients

  • Control of your schedule*

Staying Independent AND Successful

There is a lot of material out there for learning how to START a business, but we often neglect STAYING in business. This is something I had to learn on my own (thanks Kindle, Youtube, and Twitter!).

The key here is pausing and stepping back to reflect on where you are in your business and where you want to be.

If after a 3-5 years you’re still working 60 hours a week and you’re drinking the hustle culture kool-aid, but meanwhile you’re completely out of shape, not in touch with friends and family, and in front of your screen for hours on end, then what’s the benefit? (If that’s your intentional design, no problem - no judgment here)

Staying alive and happy in your business is another set of skills that one must learn.

Here are some skills that are helpful:

  • Foresight and Intentional Design

  • Humility

  • Taking action (Pivoting when needed)

Whether you’re a business owner or a full-time employee, you NEED to have some intentional design to your life. Being intentional about why you do things, your purpose, and your vision will help fuel everything else.

The Entrepreneurial Journey is a Lonely One

You will soon find it hard for your FTE friends to understand your challenges, concerns, and problems. 

You’re trying to find and define your ICP (Ideal Client Profile) and do marketing, get your pitch refined, and build your pipeline.

You may have dumped some of your savings into this new project or are stressed out about the opportunity cost of not working full-time.

If you have a co-founder, that’s awesome.

If not, but have a life partner, then consider bringing them into the business.

If that’s not a good idea, then consider forming a “board of directors”. This is a loose group of friends and colleagues who are on a similar journey as you. Personally this was one of the best decisions I made in my life. My small yet important board has been so helpful on my journey and we’ve become great friends as well. Sometimes we’re just an outlet to rant on about business and sometimes we are mirror for each other, discovering interesting epiphanies. I’m grateful for my BOD.

Whatever You Choose - Don’t Be Complacent

Whatever path you decide, it’s important to never be complacent. Whether it’s at work, in business, or even in your personal life, you must always stay sharp, adapt, but step back to reflect. If you don’t, you are increasing your chances for an outcome you may not have expected, which would lead to disappointment.

It’s our expectations that hurt us at the end of the day, not the outcomes themselves, so you must mentally and realistically adapt and prepare and then you’ll be in a much better position for what comes your way.

Happy Independence Day!

Join the conversation

or to participate.