5 min read

Where Are You Now? 4 Waypoints for Change

Where Are You Now? 4 Waypoints for Change
Photo by Aiony Haust / Unsplash

For years, I had no idea where I was or where I was going on my career journey. All I knew for sure was that I could do more.

I knew I wanted to break through the "glass ceiling" of W2 work and start something of my own. Yet, I had no map or waypoints. I was effectively "pissing in the wind" instead of committing to any sort of new path.

Would I start a company someday? Would I get a big promotion or job offer to keep me in the corporate world for a while longer? Would I win the lotto and buy an island?

Weeks, months, and years would come and go. Progress toward escaping corporate life would wax and wane. At various points I'd be inspired by a random entrepreneurial spark, perhaps getting as far as registering a domain name and crafting a logo for some web application idea. Other times a new corporate gig or promotion would make me forget about building something of my own for years.

Recently I've somewhat stumbled upon a path from "here" (executive job) to there (fulfilling self-employment) that is working for me. I believe it could work for you, as well.

Here's what I've come up with so far, including duration, income source, and support team for each waypoint:

Path Waypoint #1: Self-Discovery Work:

Duration: 3-6 months
Income Source: Stay at your current full-time job during this phase
Support Team: Career Coach, possibly Therapist if needed (healing old trauma, etc.)

This process formalized the beginning of my journey. It was the first material work and financial investment I had made, as well as the first accountable progress toward change.

I needed someone to help me through this part and keep me motivated and accountable throughout the whole thing. Perhaps you are disciplined enough to get through it on your own, but I certainly wasn't. As such, I'd recommend working with a good career coach and going through this discovery work systematically.

You should be meeting twice a month and documenting your progress along the way.

Having to pay for my own career coach was also a motivational factor. This element not only made it feel serious, but it also kept me on the hook to keep going and do something with the investment.

Path Waypoint #2: Familiar Consulting, Side Work:

Duration: 3-12 months
Income Source: Stay at your current full-time job during this phase, additional income now ramping up from side work
Support Team: Lawyer, Banker, Accountant

Doing some side work taught me a ton about myself and about business in general. Leveraging my personal and professional network, listening for problems, selling solutions, and carrying through with them. Ultimately, then, learning how to tie a value to those solutions as well as collecting payment on them.

This phase got me out of my comfort zone early and often. Sitting down with a local small business owner and helping them build a website, for example, was a totally new experience for me. I hadn't coded anything in years. I hadn't worked with a company that small, ever. Likewise I hadn't created a contract, priced my own project, or collected a payment directly from someone ever before.

Each side gig was an extremely valuable "rep" in the entrepreneurial gym, in so many ways. I strongly recommend offering familiar work (I did not go from digital marketing to being a Yoga teacher on the side, for example) so that you can create immense value and a ramp to the next phase quickly.

This phase also gets some housekeeping going. You'll establish your corporation (usually an LLC to start), a corporate checking account, some basic contracts, and you'll start looking for an accountant here.

Path Waypoint #3: Familiar Consulting, Full Time:

Duration: 12-18 months
Income Source: 100% coming from your own consulting business
Support Team: Lawyer, Banker, Accountant

This is what I call the side "step" hustle. Essentially building up enough familiar consulting business and pipeline up on the side to finally leave your corporate executive job.

I call it a side "step" because it may not be your "dream" business, but it's A business and it gets you out of your demanding 9-5 job ASAP.

For me, this step was a requirement because:

  1. I needed to equal or better the compensation I was receiving as an executive with minimal dip or ramp-up, again we are talking late/mid-career here w/associated expenses and lifestyle
  2. I didn't quite know what my "dream" business would be, but didn't want to sit around waiting for that epiphany, either

This is the phase I'm in right now.

During this phase of the journey, you're totally decoupled from your full time corporate job. You're "out" in the world as an independent resource. As woo-woo as this sounds, this step puts you on a totally different frequency out in the world.

You will notice a few things during this period:

  • Increased "luck surface area": Opportunity seems to come out of the woodwork when the world knows your intentions and availability
  • Mindset shift: I've noticed that I'm way hungrier for opportunity and more motivated to create value every day
  • Opportunity radar: Working with so many different clients and seeing so many different things every day, I see so many more business gaps just waiting to be filled with solutions.

It's during this phase that I've come to the realization that I can potentially REALLY help people with this website and newsletter. Which COULD be come a dream business. I'm not sure I would have seen that had I not taken this step first.

So, it's important to realize that during this phase we also experiment with and try out new "dream" business ideas. It's way easier to do this now because we're unshackled from our executive job. Hopefully one of those experiments takes off and turns into...

Path Waypoint #4: Dream Business, Full Time:

Duration: Forever, hopefully
Income Source: 100% coming from your own dream business
Support Team: Lawyer, Banker, Accountant

At this point on our path, we get to quit or significantly ramp down our full-time consulting business and are making a living doing what we love. Perhaps that's a yoga studio, a business incubator, or a real estate empire.

By this time we've pressure-tested our support team, we've learned how to make money ourselves, and we've been able to experiment enough to launch something that really makes our heart sing.

Perhaps your dream business is consulting in the first place, and if it is, well then you may have already figured things out in the previous waypoint. Fantastic. Perhaps this phase is a scaling phase, in that case, where you are:

  • Productizing
  • Systemizing
  • Resourcing

So that your business can scale far beyond yourself.

This is the phase I aspire to be in next, and perhaps this website and "executive escape" movement will get me there.

Boardoom Bye exists to help you with those first couple steps

Ultimately, my goal is to get you from "stuck" to "unstuck" with a rational escape route from high-earner to self-employed. I want to help you get that flywheel spinning early on. Hopefully this piece will help you understand where you are and where you could go. Where are you on this path?