What I Learned After 25 Years as a Consultant...
What I’d Tell My 36-Year-Old Self...A Letter About Resilience!
"Where you start out is not where you will end up" - quote my mom, C. Douglas.
On April 10, 2025, C. Douglas & Associates and The Inclusion Learning Lab turned 25. I worked full-time while trying to find my niche and my first customers starting in 1999, and we incorporated in 2000.
My Original Why:
C. Douglas & Associates is short for Clementine Douglas, and I am the associates. I named my company after my mother—she died two days before Christmas in 1997 while I was stuck at work, unable to take the day off to see her in the hospital.
I was angry that my manager denied my time off before the holidays and denied me the chance to see my mom before she died. No one expected her to die; her hospital stay was routine. The lesson I learned the day my mother died is that life is not promised, so if you’re going to do something, do it now.
Being a consultant in 1999 wasn’t sexy. It wasn't what normal people did. I was told by many friends that I was wasting my time. In fact, one of my children even questioned what I was doing. I think out of fear that I wouldn’t be able to keep up with the parent role of provider. (haha) My best friend at the time stopped speaking to me after telling me to go get a real job.
I never wanted to name the company after me. I had two barriers to overcome - first, I am a Black Woman without a job and no real name recognition. Second, I wanted to feel bigger - sound more important, and give folks the impression that we had some associates.
The Beginning
Where was I before I made this decision? I was first an HR and Risk Management Director, and before that, I was a Workers’ Compensation Litigation Adjuster. I left the adjuster desk right after my mother died to take a role in Risk Management after earning my Pubic Entity Risk Management Designation.
I hated my job, I hated my leaders, and I hated the dysfunctional environment. But I loved helping people return to work after an injury, and I loved helping HR leaders navigate the complexity of integrating workers’ compensation best practices into the work environment.
How I Arrived in HR
I initially took the role of Risk Manager for a 14,000-employee, woman-owned multi-state day labor and temp labor company. Six weeks after accepting the role, the owner popped her head in my office and said, “How would you like to become our new HR Director?”
I responded, I know nothing about HR. She said, “You know people, they like you, I’ll hire a good lawyer to help you, because I just fired the HR Director and you are replacing her.” (Like WTF)
I knew in that moment, this was another dysfunctional work environment, and I was either going to drown or be swept out to sea as the HR leader who was also responsible for making sure no “day labor” hire jumped off the building because they were too high when we hired them at 5 am.
I’m not even sure if the Day Labor industry still exists, but in 1998, it was a big deal.
Twenty-five years ago, I quit my job.
When is the right time to leave?
At the point where my “side-hussle” was making enough money to support my family, I quit my job. Cashed in my retirement. "Who needs retirement at 36?" When I talk to founders now, especially white male start-ups, I hear them saying we need funding. I am looking for investors. That is never an option for a Black Woman. Less than 1% of start-up funding goes to Black Women.
Critical lesson: invest in yourself now. If you cannot invest in your own business how do you expect anyone to invest in you?
Back to my journey to today…
Bought a used Honda Accord with cash. Lowered my overhead expenses and we were in business.
I printed business cards, packed my 7-year-old into the car, and hit the road to find customers. A wonderful man, Tony Abella, Jr., was the insurance agent for my former company, and he believed in me and gave me my first client. (I say your name every day).
I pitched him on combining HR and Workers’ Compensation into a consulting role. If I could help organizations hire the right candidates, keep them safe at work, and return them to work after an injury, their insurance premiums would remain low. Intern as their insurance agent, he would be able to find a market willing to insure them, and he would increase the retention rates of his client companies. An all-around win-win for everyone.
This is what repurposing your experience into a business looks like. In reality.
The Twenty-five Years in a Cliff Note:
I had a vision—and zero patience for people who didn’t match my intelligence telling me what to do.
I built a business.
I raised two sons
At our peak, I employed 12 consultants.
Then the 2007 - 2008 - 2009 hit.
A client filed for bankruptcy, owing us $50k billed and $50k unbilled.
I couldn't keep my office open - I shut it down and moved home. (Early remote work adopter)
Laid everyone off - went solo again. The cubicles from my old office are still packed neatly in my garage. The plan was to run a home office for a few years and return to a rented space. (At some point, I’ll empty the garage and donate the desks to a non-profit.)
I started over.
I’ve started over more than once. It’s not failure—it’s resilience.
You don't get to 25 years with BS and pretend success.
I’ve been a single mom at 21.
A divorced mom of two sons at 50.
I got married again at age 59.
A keynote speaker in 8 countries and over 500 conferences.
Author of 3 books, working on number 4.
I don’t sleep much—success, worry, anxiety, client stress, marketing, refocusing, and everything in between keep me up at night. But I earned every blink of it. Every damn second!
To My 36-year-old Self:
In retrospect, I should have been scared s..tless to quit my well-paying job to try to start a business with two children, and no real start-up funds. But at 36, I was fearless. Here’s what I wish I knew back then and what I would tell 36-year-old Margaret in retrospect,
✅ Do it faster.
✅ Trust yourself more.
✅ Forget the world’s opinions.
And to anyone who doubts you—say f**k you and keep moving. For everyone who said I want to hire you but didn’t for whatever reason, don’t spend one minute thinking about them.
For every client who underpaid you because you were the “small’ consulting firm and they paid the big boys more, keep moving forward and never give them a second chance to underpay you.
The first time was a necessity; the second time, you're undervaluing yourself.
So You Want to Be a Consultant, Really? Why?
To anyone brave enough to quit a six-figure job to start a consulting company today, here’s my advice. The people who take your calls today will ghost you tomorrow. The second you are on the other side of the fence, they will immediately realize you have nothing to offer them, and they will stop answering your calls. Be okay with that.
You have 30 days from the time you quit to make all the connections with your past stakeholders before they turn the lights off and forget who you are. Make use of those thirty days.
You need a lot of courage and a ton of faith. You will either become super religious or you will find a spiritual guru to keep you going. You will spend a lot of time in the valley. Consulting is like being between two mountains. When you climb to the top, you realize that there is another peak left to climb. When you are in the valley, here’s what you need to know:
👉 Never grade yourself by social media. It’s a highlight reel.
👉 Most people are lying.
👉 This journey is a grind—valleys and hills. Just keep climbing.
👉 Do the work. Celebrate every damn success you have!
👉 Assume you know nothing. Learn everything.
👉 Cover your bases.
👉 It’s okay to go solo.
👉 Find a life partner who believes in your dream...fully! This is the biggest lesson I had to learn. If your partner doesn’t support you and becomes jealous of your success, your life and business are doomed.
👉 And if you have to start over—do it. No shame in that. Go back to a regular job and come back when you're ready. Seriously, if this s**t gets too hard, hit pause, return to a regular job, retool, rethink, and be willing to try again. The second time, you will be wiser.
What's Next for Me
🌹 25 + 10 more years.
🌹 My current why and my mission: To make sure my 3-year-old grandson, Douglas, doesn't enter the dysfunctional world of work that exists today. If I get this right, he will be your boss, or his own boss, and never your employee.
🌹 Unshakable purpose in the work of inclusivity and women’s empowerment.
🌹 I’m just getting started. Betty White didn’t become a household success until she was 63 and peaked at 70. Technically, I am right on schedule.
Introspective Note to Myself
To my 61-year-old self, know when to quit. Know when to walk away...know when it's time to leave this s**t to the next generation. I never want to be old and fighting for a place in the process that has left me behind.
This business is a vehicle to help others; it does not define me, and I can at any point let it go. This is a lesson that many do not know how to embrace. Learn this lesson early and remind yourself often - that there is a life after being a founder that does not include trying to stay on the stage.
Where Am I Going After This?
I will eventually exit to the beach, and a rum 🍹 is on the horizon - Jamaica is in the future 🇯🇲 🇯🇲 🇯🇲...leaving the diaspora and returning to my place of birth was always the why…that drove the what.
In the interim, mentor, teach, learn, and give back...📣
Finally, celebrate your success...Margaret 💃🏾💃🏾🙏🏾 - As women, we need to celebrate what we’ve done to get to today. So celebrate with and for me, and every other woman on this path.
(Thank you for reading this personal journal entry.)