“True wealth is not of the pocket, but of the heart and of the mind.” — Kevin Gates
When I left my corporate sales career over a decade ago, I had no master plan or playbook to follow. Just a desire to do more meaningful work, regain control of my time, and build a business around my strengths.
That journey has been anything but linear. But looking back, I can now see three distinct stages that helped me evolve from a solo freelance coach to becoming a portfolio entrepreneur that spreads my risk and reward across three distinct pillars.
- An instructor, facilitator and executive coach for Oxygen
- A partnership with an executive coach providing 1-2 year comprehensive leadership development programs to growth-stage organizations
- Private business coaching for clients who are B2B experts looking to simplify their business and productize their offers
I recently sat down and shared this path with a client and I thought it could be helpful to others — a roadmap of sorts for coaches, consultants, and fractional executives who want to break free of the time-for-money gig, build a steady business without burning out, and leverage their expertise for capturing more value.
Important note: You don’t need to scale like a startup. You just need a structure that fits you and keeps your sanity intact.
Here’s what that can look like.
Stage 1: Use your existing skills as freelance contractor or fractional professional
If you have existing skills & experience, contracting with organizations that need your expertise is probably the simplest option.
When I started my freelance coaching business 12 years ago, this didn’t register as an option for me.
Today, I love it so much that it’s a key ingredient in my portfolio entrepreneur recipe.
As I described in this article, I see portfolio entrepreneurship as the easiest path to flexible and meaningful work that leverages your existing skillset.
In my case, the skills I’ve developed over the last decade include coaching, facilitation, and teaching/training. I use these skills to lead virtual cohorts and do virtual training + coaching for a leadership development company called Oxygen.
I also get to utilize my experience and skills gained from 15+ years in startup and corporate settings. By blending all of this together and positioning my value around these skills and experience, I can work for a company like Oxygen a few hours a week and still have plenty of time for other professional or personal pursuits.
And the best part – you only need one or two of these engagements to replace your corporate income and cover your living expenses.
From my perspective, if you’ve never ventured into the entrepreneurial waters before, it’s probably best to skip the pure entrepreneur route and go straight to being a freelance contractor or seek a fractional role.
This significantly reduces risk while allowing you to test your skills in the marketplace and still have a lot of flexibility to pursue your personal projects in parallel.
In this stage, I’d allocate my time as follows:
- 1 hour per day researching and exploring potential contract and fractional opportunities (research)
- 3-5 hours per week networking and reaching out to organizations that seem like a match (outreach & referrals)
- 2-4 hours per week demonstrating your skills and showcasing your value with prospective organizations (proactive outreach & follow-up)
- Create short Loom videos demonstrating your skills
- Offer to take on an initial project to prove your value
- Create a proposal that addresses a need or solves a painkiller problem
- 1 hour per day writing content on LinkedIn that showcases your skills and experience or commenting on other LinkedIn posts
- The rest is filled with pour-over from any of these
The key is to hold the intention of evolution in your mind so you don’t get trapped in this stage.
Stage 2: Build your skills and evolve one layer
Once you’ve secured work that leverages your existing skills & experience while paying your bills, it’s time to explore other pillars of opportunity that are more personal.
For me, this looks like partnering with an executive coach to offer workshops, training, and executive coaching in the form of comprehensive leadership development programs for mid-market growth stage companies. Most of this work is based on year-long retainers with single organizations.
I also have my own private 1-1 clients. I’ve nurtured this part of my business for years and it’s 100% referral based.
A valuable lesson I’ve learned over the years is that you can only take on so many private clients if you want to maintain your sanity, energy, and minimize the number of hours you work.
And if you want to maintain a simple one person business, you’ll need to identify the path that allows you to maximize your value, minimize your work time, and do it without hiring a bunch of full-time employees.
Fortunately, I’ve discovered this route for you, so you don’t have to go through years of trial and error like I did.
Here’s what I would do at this stage:
- Build a following with writing and selective networking – don’t waste time creating YouTube videos, a podcast, or writing a book just yet. Share on one social media channel and start a newsletter to practice getting your thoughts and ideas out into the world and sharing them with others. If you want to see a good example of this, just look at the activity for Catlin O’Shaughnessy on LinkedIn.
- Evolve to a new client model – create a loosely-held curriculum and take on more clients in a group coaching format. This brings your client work down to 1-4 hours a week while increasing your revenue. I’ve done this with entrepreneur coaching groups as well executive leadership and manager training cohorts.
- Evolve for fulfillment and flexibility – remove time-suckers like 1-on-1 calls, set boundaries on how many hours a day you’ll work, and restructure how you deliver to your clients without reducing any value.
Now, thanks to my hard won experience, you’ve just increased your earning potential from $100k per year to $200k+ per year while working no more than 5 hours per day.
Stage 3: Productize your expertise
You can productize your expertise and unlock even more income, impact, and flexibility.
In this third stage, you will:
- Codify your experience, skill, and expertise into a proven structure that represents everything you’ve done to get results in the two stages above. You restructure time-consuming aspects of your work so that you can package and deliver a specific service over and over again. This creates more efficiency in your business, and thanks to your growing following and reputational capital, you’ll likely increase your earnings even more while working the same amount of time. I’ve supported dozens of clients with this. Here are a few examples …
- A second option in this stage is to build a standalone digital product – use your teachings and results from your client work to build a successful entry-level product. You build it once and you can use it to nurture clients at a lower price point while adding to your income.
- Leave 1-on-1 client work if you want. You may see a dip in income at the start, but that newly allotted time is used to focus energy on your productized offer, experiment in new areas, or just enjoy more downtime for yourself.
Again, thanks to my 12+ years of experience, you’ve just increased your earning potential from $200k+ per year to $500k+ per year – without adding more hours to your week.
This is where rapid iteration comes into play. You must detach from manual labor and solely bank on your creative ability.
Your time is allocated to:
- 1-2 hours per week fulfilling your productized cohort program
- 1-2 hours per day writing content to fuel growth
- 1-2 hours a day building or refining projects that take you even further
You can build new products, branch out of the one-person business, or just enjoy life for a bit until early retirement bores you enough to start meaningful building again. 😉
You’ve now built so much credibility and expertise that you can probably sell whatever you want.
If you take nothing else from this, keep this in mind: You don’t need to build it all at once.
You can start with what you know.
You can grow with time, experience and credibility.
And eventually, you can productize your wisdom + knowledge while working the same or less while earning more.
For me, this path is about building a business that actually fits your life. One with plenty of room for creative energy, long walks, afternoon workouts, and making a meaningful contribution.
So whether you’re just getting started or looking to evolve to your next stage, I hope this gives you a framework, and the permission, to build it your way.
Live bravely,
Michael
P.S. If you were to design the next chapter of your work, what would it look like?
