What does it really mean to be productive? It’s a question I’ve been sitting with—especially as...
My business is officially 18 months old. That milestone, combined with countless conversations with friends and former colleagues who have also struck out on their own, has me reflecting on this entrepreneurship journey — what has gone well, what surprised me, and what I wish I'd known sooner.
If you're running your own thing — or thinking about it — I hope something here resonates.
1. Get your tech stack right, and make sure it talks to all your calendars.
This one is still a work in progress for me, honestly. Here's where I've landed so far: I built my website on HubSpot's CMS and use their CRM as well — both on free plans. I use Gmail for email alongside the Microsoft Office suite, and I rely on Calendly to sync my calendars and manage scheduling. On the AI side, I have paid plans for both ChatGPT and Claude. When you're operating solo, your tools need to support the way you work. Scheduling conflicts and siloed systems are a tax on your time and your sanity. It's worth investing the effort early to find software that integrates cleanly across your whole setup.
2. Build in operational checkpoints — and hold yourself to them.
I set quarterly goals for myself, and I block time during the first week of every month to document how I'm tracking. My goals aren't financial targets. I focus on things like number of clients, new types of experience, continuing education, and networking activity. That regular cadence also creates a natural moment to step back and assess the business itself — which services are most popular and most rewarding, where pricing needs adjusting, and whether there's anything I'm offering that no longer feels like the right fit. That kind of reflection is hard to do on the fly. Protecting time for it makes all the difference.
3. Watch for old habits creeping back in.
When you leave a structured corporate environment, you bring yourself with you — tendencies and all. For me, that means staying vigilant about being decisive, maintaining clear boundaries, and not underselling myself. These aren't one-time fixes. They require ongoing attention.
4. Time management is a bigger challenge than you'd expect.
Running a business means doing a lot of things for the first time — all at once. Executing your services. Writing proposals. Sending invoices. Managing your own schedule. Even with great AI tools, everything new takes longer than you think it will. Give yourself grace on this one, and build more buffer into your days than seems necessary.
5. Make time for learning and experimentation.
In a corporate setting, you absorb knowledge from colleagues constantly — through osmosis, through meetings, through mandatory training. As a solopreneur, you have to build that structure yourself.
For me, this means building continuing education into my quarterly goals (I have a certification to renew every three years), carving out time to experiment with new AI tools, and attending webinars that keep me current. If you don't protect this time, it disappears.
6. Support your people — genuinely and without strings attached.
Like and comment on the LinkedIn posts of your clients, friends, and colleagues. Follow their company news. Send a text when you're thinking of someone. Check in just to check in. This kind of generosity matters, and it compounds over time. It's simply the right way to move through the world.
7. Don't let your network go cold.
I've always been someone who stays in touch, and I count that as one of my genuine strengths. Still, it helps to have a system. A quarterly or biannual calendar reminder to schedule coffee or lunch with the people who matter to you is a small investment with an outsized return. Your network is one of your most valuable professional assets. Treat it that way.
8. Build your own "expert board."
It can feel a little strange — at this stage of a career — to be the newcomer in the room again. It's humbling to ask for guidance on things you'd be expected to know. The good news is that you probably have something more valuable than answers: an extensive network of people who've been where you are.
I lean on a few fellow coaches, including my former coach, for perspective on everything from program design to pricing. I turn to my dad, who had a long and successful business career, for broader perspective. I offer the same in return — to new coaches, to my husband as he builds his own business, and to friends navigating similar transitions. Find your people, and be one of those people for someone else.
9. Your work is your reputation. Protect it.
More than ever before, the quality of what I produce reflects directly on me. That means I sometimes spend more time than I technically need to on a proposal, a client report, or a piece of content. Integrity is the standard I hold myself to every time.
10. Lead with value.
I've believed this for a long time, and running my own business has only reinforced it. Patrick Lencioni captures it well in Getting Naked — his recommendation is to jump in and start consulting right away — even before you've won the business. The value you provide speaks for itself.
This approach fits naturally with coaching. Coaching only works when the person on the other side is genuinely engaged and committed to their own growth. I go into conversations focused on what's possible. I ask questions. I listen. If there's a fit, it becomes clear on its own.
11. Practice gratitude. Seriously.
Years ago, I read a book on happiness — I believe it was The Happiness Advantage by Shawn Achor — and one idea has stayed with me ever since: you can actually change your brain chemistry through behavior. When you consistently focus on what's good, you develop neural pathways that naturally orient toward the positive. Neuroscience backs this up.
One of my favorite ways to build this muscle is keeping a gratitude journal. Three or four minutes before bed. That's it. The habit means one of my last thoughts each night is something I genuinely appreciated about the day — something like dipping my feet in the cool water of our pool while working outside. Small, simple, easy to forget. The journal helps me hold onto it.
Eighteen months in, I'm grateful for every part of this — the learning curves, the surprises, and the deeply rewarding moments in between. If you're on a similar path, I'd love to hear what's on your list.
