Tales From A Newspaper Delivery Girl, Lessons in Delivering Good Work
I used to deliver the Boston Globe as a kid, waking up at 6 a.m., rain or shine, my next door neighbor and I split the route. Success wasn’t measured by accolades or performance reviews; it was whether the newspaper got delivered, dry and intact, and whether we got a tip at the end of the week. Sometimes the paper got wet, sometimes it blew away, sometimes there was no tip at all. What mattered was holding ourselves accountable, showing up, and constantly asking: Did I deliver - literally and figuratively?
That lesson stuck with me as I navigated the corporate world in the 90s, working for global firms like Ogilvy, KDDI, and MCI. In those companies, structure, processes, training, and hitting KPIs guided our success. Milestones were clear: hit your targets, deliver your campaigns, meet your metrics. As employees, you knew when you were on track or not.
But my journey in tech wasn’t always easy especially in the 90s. In fact more times than not I was the only woman in the room, part of the less-than-5% rule. I remember walking into meetings where male colleagues would wipe my winning quota off the whiteboard. I would hear comments from women questioning how I looked, walked or talked. Eight times out of ten, I was the lone woman in the meeting. Looking back, I’m not entirely sure why I stuck with it—but my passion for the work, outweighed the noise in the background. That focus and perseverance is exactly the mindset required to run your own consultancy or a strong six-figure business.
Entrepreneurship doesn’t come with a roadmap. There are no KPIs set by someone else;
Which is the correct way to go?
our milestones are whether we have signed agreements, clients, dollars, cashflow, and referrals. And just like in those early newspaper days, how we really know we’re doing well is how we hold ourselves accountable. Are we delivering work that truly matters to us? Is it stand-up, stand-out? Is our pricing and processes competitive and fair. Are our clients not just happy, but are they thrilled?
When Doubt Creeps In
Doubt is part of the journey. It will creep in, and that’s okay. Rather than running from it, lean into it, in fact listen to it carefully. Sometimes the doubt is telling you something valuable: maybe you low-balled a quote, rushed a job, or skipped hiring help for a task outside your expertise. Instead of fearing it, learn from it. Ask yourself what the doubt is pointing out, and use it to course-correct.
Grab the doubt - what is it pointing out?
Assembling the Plane on the Way Down
Entrepreneurship often feels like assembling a plane on the way down. You’re building as you go, figuring out processes, juggling multiple roles, and learning from mistakes in real time. It’s exciting, terrifying, empowering, and humbling all at once. Solo entrepreneurship, in particular, requires curating an ecosystem of contractors and collaborators who share your vision and bring something unique to the table, something you are collectively proud of.
Empowerment, Freedom, and Accountability
The beauty of this path is the freedom it brings—the freedom to make decisions, set priorities, and create the life you want. But freedom without accountability is chaos. True empowerment comes from taking ownership of your work, asking the hard questions, and consistently evaluating whether what you’re doing is worthy of your best effort.
So whether you’re an entrepreneur, freelancer, or stepping into leadership, remember: the plane is always in the air, the newspaper still needs to be delivered, and doubt isn’t your enemy it’s your guide. Ask the questions, listen to the answers, and keep building.
Are you delivering good work? Is it stand-up, stand-out? Tell me your story!
Stand up and stand out!