I found my life’s work in the mailroom. And, it led to one heck of a wild and rewarding ride.

At public speaking events, I’m often asked to share my story. When I share that I’ve worked with business owners for over 40 years, people would stare back in a way I could tell they were doing mental math. Once they arrived at a number, their head would tilt like a curious dog. The calculated age and who was before them didn’t match.

I’m 57. Forty years in means I started at 16. A major head start from the traditional path of college to entering the workplace to finding your niche. Mine was accelerated. Quick. But hard won.

I know it’s not popular for women to state their age. I offer it up because 40 years doesn’t mean I’m at the end of something. It means the runway started early, the experiences vast, and there’s a long stretch of it left.

What the head start actually bought me wasn’t just years. It was rooms. Relationships. Unique skills. Lived experience. Every one of them built a different piece of who I am as a leader, and not one of them built the same piece twice.

Ownership Starts Smaller Than You Think

My first few jobs set the stage for an unconventional path. The first was a paper route with 28 customers, inherited from my brother, who went on to build a business of his own from the ground up.

Plenty of business builders started the same way. Warren Buffett was running several routes by 14 and filed a tax return on the income. Tim Cook delivered the Mobile Press Register at 11. A route is a small business — customers, a schedule, receivables, and a margin you keep or lose. Nobody calls it that when you are a kid.

I was young. No boss looking over my shoulder. Tested by New England weather. You couldn’t call in sick. If you didn’t collect money, you didn’t get paid. It was a master class in self-reliance and entrepreneurship.

When I look back, I really can’t remember too much of childhood that I didn’t work. The route was first, and then part-time jobs followed as soon as I was old enough to apply. Fotomat was next up. Yup, the little blue and yellow booths in the middle of the parking lot where film was dropped off to be developed. Like newspapers, yet another service that has gone extinct.

Similar in experience. Working 100% alone. You opened, closed, reconciled cash, made deposit drops, handled inventory, customer service, sales, and so on. Everything. I don’t know how they got kids to do that job. Not just the isolating booth. Handling business from A – Z, with no experience. And very little supervision. They both were so self-directed, you had to have an entrepreneurial drive to succeed.

Know Your Worth

I learned a ton, including a lesson I didn’t see coming. After several months, I was gifted the not-so-generous hourly increase of 11 cents per hour. A merit increase. But I was crushed. I had performed. I got praise. I worked hard. I was dedicated. I filled in when others couldn’t cover their shift. I thought the effort would pay off more. It didn’t. The lesson came . . . know your worth.

Falling in Love with What’s Hard

Those days gave me some insight into what business owners encounter. People hear owner and think freedom. What it actually means is that everything lands on you.

Every problem, customer complaint, and issue is your responsibility. If you don’t show up, you don’t get paid. No PTO or other employee benefits. Vacations get put aside to keep up with the demand of work. I think this is why entrepreneurship and business owners have a special place in my heart and a common thread throughout my career.

A Dream Is Not a Direction

After learning the financial trajectory of the little booth, I moved on and took on two new part-time jobs. One I thought was going to be my professional path and one that ended up being that path. An animal hospital. A sales corporation.

I had always dreamed of becoming a veterinarian. I had a deep love of animals so becoming a vet tech was a natural first step. I saw what was behind the curtain at a young age. Quickly found myself facing life-or-death situations. Critical thinking in the face of high-stress environments was instilled in those early days. It wasn’t always pretty. I think I hoped the service would outweigh the heartbreak. It didn’t.

I think it is easy as a kid to romanticize a role. Like any service job, it is a business at its core.

The First Plan Is Only a Guess

These early experiences made the dream less attractive than it once was. Especially when a different path became so much more exciting.

The mailroom. Exciting right? Well, I didn’t spend much time there, but it kicked off what would become quite a launch pad.

I came to this organization with some skills needed to manage a business. I may have looked confident, but what was really there was a belief that I could figure out almost anything you put in front of me. I was like a sponge. I loved hands-on learning. I had an entrepreneurial spirit combined with the love of seeing others succeed. When those things combined in the same space — I was hooked. It was like rocket fuel.

It wasn’t long before I was moved to the customer service department after they had a large turnover. Nobody was left to help train. Pretty much just jump into the frying pan. Thankfully not my first experience with high pressure, figure-it-out environments.

I went from answering the phones to supervising to managing in quick succession. Solving hard problems became the backbone of my career along with serving and teaching others to serve. It’s important. Being on the front lines of fixing for an organization is hard work. How different would the world be if everyone had to do it at least once in their career? 

Learn the Whole Business, Not Just Your Part

Battle tested, I was ready for even more, so I made stops in almost every major department in the company including accounting, data entry, operations, and marketing. Marketing created a real spark. Learning how to attract customers by creating a compelling message. Joy!

I went from newsletter writing and production — I remember the days of hand-cutting and placing headlines — to product photography, promotions, catalog production, contesting, collateral creation, ads, events, you name it. I loved connecting the customer to the product and seeing sales increase. Loved it!

A hungry, willing to learn, workaholic combined with a fast-growing organization who valued people who could get things done. It was a wonderful match. It provided a training ground that no MBA program could compete with. Hands-on. Fast-paced. Real pressure. Heaps of responsibility. Direct results.

Confidence Is Built, Not Granted

The promotions and role changes came fast and furious. The pressure did, too. In my early 20s I found myself elevating to the role of vice president. What was believed to be the youngest in that industry. When I attended industry events, the anecdotal evidence seemed to agree.

It was such an exciting time, even though I had to fight hard to be taken seriously in those early years. I got to be with people making real moves. A front row seat and business education that was broad and rich. The amount of direct input and guiding was impactful. Both for me and the organization.

That room built the parts I still lead with. Service. Knowing what mattered most. Teaching myself and others whatever the job required. Taking on hard projects. Focusing on growth and development. It also built confidence, which is a strange thing to earn at 22 with a company that simply never asked whether I was capable, only if I was old enough to handle it.

While my peers were collecting diplomas at 22, I was running a department they hoped to be hired into. For years I carried the pressure to go back and finish my degree. In rooms where everyone had taken the traditional route, I braced for the question before it came. I had an answer ready and I never liked using it. After a while the question stopped coming. The experience answered it.

Knowing What It’s Worth Isn’t Knowing How It Grew

Though the path was unconventional, I wouldn’t trade those experiences for the world. Well, maybe a few along the way. Business comes with some hard knocks.

I had risen to the role of Executive Vice President leading every major aspect of the business. The pressure was immense. The hours were long. The learning continued. The weight of responsibility heavy. Late in that run I got lessons no higher executive wants to have.

Around year 18, it was time for the ownership to sell. I got my first experience with venture capital groups. Everything changed. Everything. Change even changed. Eventually, even the growth.

Those few years of decline at the hands of people who saw value in the business but didn’t honor how to grow it were some of the hardest of my life. Having to navigate that with people who had become like family was excruciating. I took on a ton of the stress. I felt it mentally and physically. I fought hard against the fall. No matter how much I pushed against it. The battle was lost.

I still bear the scars of those transitions. Speak to anyone having experienced a tough transition and you will see it in their eyes before they tell their story.

Coming Apart Teaches What Building Cannot

Nobody teaches it. Building has a hundred books. Coming apart has none. That room built perseverance, and it built the ability to stay in a thing that is ending without pretending it isn’t — which is the single hardest thing I have ever asked of myself as a leader, and of those I led.

Twenty years there, and I was done with the industry. Done. Done. Done. I couldn’t imagine giving my heart and soul to a similar organization. While I didn’t know what would be next, I declared it wasn’t staying in the same industry. Too painful. It was like the worst breakup I had ever experienced. Call in the divorce lawyer. I wanted out. Until, through an acquisition, I was introduced to my next wild ride.

Action Replaces Uncertainty

With no title or defined role. No clear path forward. Only a desire to land what was left of the plane, I agreed to help transition the salesforce to a new organization. That brought my next MBA lesson: don’t try to land a plane that is in freefall. It was messy. Promises broken, misinformation, accusations, hurt, loss of income. As quickly as a VC group arrives, they disappear faster. Leaving behind every messy element of a high-speed crash.

All I kept thinking was make it stop. Get out. Find the next path. But much like this first organization, this path found me. As the dust settled and the smoke began to thin, it was clear there was much to be done at this new location.

Your Actions Tell the Truth First

I spent a year telling myself this was all temporary. Commuting from the East Coast to the Midwest weekly, only to help. The story I told said one thing, my actions proved I was back in the fight. The entrepreneur spirit too strong to be silenced. I wasn’t landing a broken plane; I was fighting for growth with a new sign on the front of the building.

After a year living in denial, a real estate friend of the ownership called to introduce himself and announce that I was embarking on a house search in Ohio. The time to relocate had come. That was as official as the offer got. I hadn’t been kidding anyone with my temp story. I had already signed on months before. They saw it before I did.

Off to Ohio I went with the plan to give this opportunity a max of five years. In a flash, five turned into 20. I had never seen myself relocating. Especially not to the Midwest. Nothing against the area other than it was too far away from family and the ocean. Where the heck was I going to get good seafood? Spoiler alert, not in a landlocked state.

The leadership here was young and hungry, too. They loved to remind me that I was one of the older staff members in leadership, even though I was only in my mid-30s. While this was a corporation as well, it operated like a start-up. Loose, fast, and ready to take on almost anything without being jaded or slowed down by the worry that it might not work. It felt like my last home.

My east coast vibe meant I spoke a different business language from the ownership of this firm — to this day I try to curb my New England accent to avoid teasing — yet one thing cut through. I wasn’t afraid of work and pushed hard for growth. Willing to do whatever it takes. As much as I didn’t fit, I fit.

I wish I could recap all that happened in those 20 years. The truth, some of it happened so fast and moved to the next thing so quickly, I struggle to remember details.

The best recap I can give is the title and position changes came almost as fast as my last organization. From no title, to Director, to Vice President, to Senior Vice President, to Chief Strategy Officer. With each role, not much got taken away, just more acquired.

The Work Makes the Case First

Some people sit in the same position for 20 years. Others have to move from organization to organization to move up. I’ve interviewed enough people to know which pattern is common now. I got to prove greater worth over and over within the same organizations. It allowed me to move up without moving on.

None of it was handed to me. More often than not I put in the work first, then talked to leadership. I was in organizations that valued people who would jump in and do, even when it wasn’t in the job description. The work made the case before I did. Not every organization operates that way. Where it doesn’t, the ask has to come first — what would it take to qualify. Either way somebody has to raise it, and most people never do.

Endurance Is Not Drive

I have always been career first, so going all in was natural. We always said we worked hard and played hard. Over time that got replaced with work hard, and then work harder. Even the really hard times provided lessons I carry with me today. So many lessons they are too plentiful to recount how each arrived. But they did. Probabilistic thinking. Calculated risk-taking. Emotional self-regulation. Comfort with chaos. A bootcamp for business builders.

There were so many people that I hold dear. We shared so many laughs. Some tears. During my 20-year tenure I spent time with some of the most talented people of my career. I developed relationships with some of the most gifted salespeople I’ve ever met. In a sales organization the sales team has you outnumbered by a large margin. Relationships are complex. Personalities, styles, backgrounds, and preferences are broad and wide. I became a practitioner of communication, language, relationship building, and a student of psychology and human behavior. Developing people was not something I did alongside the job. Most years it was the job. Being able to coach, train, and grow revenue in such a hands-on way was a gift.

Twenty years of that builds endurance, and endurance is not the same thing as drive. Drive gets you into the room. Endurance is what you need in year eleven, when the number went up again and the pace never came back down. That room built the muscle for staying. It also shaped me. I conformed to the style of leadership that environment rewarded, and I did not see how much until I was standing outside of it.

Stretch and Extraction Look the Same From Inside

There was a cost in exchange for that gift. Though stretch is necessary for growth, the stretch was intense. If the intensity waned, it was suggested that it was because we weren’t pushing hard enough. Even though for many years, we struggled to keep up with the growth.

What that taught me is the thing I use most now. There is a stretch that develops a person and a stretch that only extracts from them, and from the inside they can look identical. The difference shows up later, in whether the person is still standing and still willing. I did not always call it correctly. I know how to call it now because for 20 years I was on the receiving end of it and applying it to other people at the same time. 

Every Build Asks Something Back

What I can tell you is that both organizations provided executive roles that were hands-on. No delegate to your team and go play golf. The price paid in those roles is extremely personal. I traveled a ton. I put relationships on the back burner. I said no to so many invitations that after a while they stop coming. I lost whole sections of my life to the busyness of the business. I did it in the name of success. In the pursuit of building something. There is also a trade you make in return.

It started as a measured compromise. Time for money. Presence for progress. A fair trade, or close enough to one. Then it stopped being measured. The trade kept running in one direction and I kept agreeing to it.

What kept me up at night changed too. Not the numbers. How to build. What kind of leadership the next stretch would take. What the building was doing to the people inside it. That question became an obsession.

What I found was I had become one-dimensional while I was encouraging others to live fully. I still loved the build. I wanted a different way to develop.

Speed Makes You Think You’re Alone

I’ve already established that I love to learn. I love challenges. I love to move forward. That was what sparked looking for lessons the organization could no longer provide. They weren’t within the walls any longer. So, I entered a number of certification programs and the one that felt like home was coaching.

Let’s face it, there are a lot of industry experts that become coaches. If I decided to choose that path I wanted to hone my skills to a higher level. I wanted to combine four decades of executive experience, building businesses, and hands-on know-how with the art of helping others achieve greater heights — the part of the work I had been doing longest.

In that program I was introduced to a number of executives that had experiences like mine. They were on the tilt-a-whirl. They were fighting for their dimensions to stay alive. Before this time, I felt isolated. Like we were the only organization that worked that hard. Were that dedicated. Were that hungry. Really that was just because we were too busy wrapped up in our world to see that others just like us were in the same whirlwind. It is far more common than most would think.

Range Is the Whole Point

Here is what I did not understand until I was outside of it. A bottoms-up build hands you range. I have reconciled the drawer and I have sat in the seat where the number gets set, and I did both without anyone explaining either one to me first. While it was an untraditional start to a career, it provided a perspective that is unique. It is also what makes the work possible now, because developing somebody requires knowing what the room they are standing in actually feels like. What it requires. What elevated skill looks like.

As I launched The Force Collective, it was with my entrepreneurial spirit in one hand and the desire to connect other executives, leaders, and business builders to trades they may be making. This time I’m helping others to connect with how they build. Build a way that you can still be growth focused with a wider lens. A build that doesn’t ask you to trade your core.

You have rooms too. The role you assumed knowing you had a lot to learn. The path you stayed on even though there was another pulling you. The scars you are still healing. The stretch that extracted too much. Each of them built something, whether or not you have ever named it.

Most people never take that inventory. They carry the pieces without knowing what they have, and the next room feels like starting from zero. It isn’t zero. It never was.

The question was never how you got here. It is what the getting here built — and whether the next thing you build is one you can stay inside. Take the inventory. Then build deliberately.

Build Something You Can Live Inside.