Written by First and foremost, I love living in Massachusetts. Yes, I’ve heard the nicknames given to the residents, and while I’m not from here, I appreciate that Bostonians and Massachusettsans (or Massachusites) are some of the most down-to-earth, shoot from the hip people I’ve ever met. The nickname (which begins with “Mass” and ends with “hole”) may seem derogatory, but it’s earned because what you see is what you get. Folks here don’t waste time on small talk or pleasantries and aren’t driven by the need to make you feel special. If they like you, it’s genuine. If they don’t, you’ll know it. Pretty straightforward, if you ask me.
Now, when it comes to driving in Massachusetts, that’s another story.
While I love the people here, I hate driving here! Don’t get me wrong, I’m from Florida, and they established road rage laws for a reason, but up here, it feels more personal when you get that honk or one-finger salute. Escaping Boston on a Friday made me realize there are quite a few lessons entrepreneurs could learn from watching Boston drivers.
Lesson One: Patience, Kindness, and Planning Ahead
There’s nothing quite like using Google Maps and watching the estimated time creep up because you’re stuck in traffic, or even worse, because cars keep blocking the intersection, and when the light turns green, no one can go anywhere! You quickly learn two things: 1) plan ahead – give yourself an extra 20 to 30 minutes, and 2) be patient – honking, yelling, or gesturing won’t clear the intersection.
The same goes for business – whether working with a team or solo, planning and patience are essential. If you’re collaborating with freelancers, remember they’re freelancers for a reason – you didn’t want the responsibilities of hiring employees (health benefits, taxes, and the laws that govern them), giving you more control over when and how they work. For those doing it all themselves, there’s only so much you can do in a day. Burning the candle at both ends will leave you with nothing, and if it’s just you, what happens when you burn out?
We may also fall victim to shiny object syndrome or the urge to keep up with others. If someone in our niche launches something big, we feel we need to do the same. Take some time to truly evaluate that urgency. Does it really need to be done today or this week, or have you slipped into “I want what I want, when I want it”? If it’s the latter, take a step back, breathe, and remind yourself that planning minimizes mistakes and increases the success of launches. Be patient, take your time, and while it may take a bit longer to realize your idea, you’ll be grateful for the results in the end.
Lesson Two: Opportunity
I’ve lost count of how many times I’ve seen someone take the shoulder illegally when we’re stuck in traffic. Sure, there are times you can use the shoulder, but that “Bus Lane Only” sign was a clear indicator that this wasn’t the time or place. Still, you have to admire those who seized the opportunity. They took the time to evaluate – traffic was at a standstill, no buses in sight, and they were far enough on the bridge that the likelihood of a police officer spotting them was slim to none – and decided the rewards outweighed the risks.
The same goes for business – there are countless opportunities to grow and learn. Especially for seasoned business owners, it’s easy to fall into patterns that worked in the past. But times are changing, technology is evolving, and with AI entering the scene, we can suddenly find ourselves left behind if we’re not willing to adapt. By the time we realize the importance, we’re already playing catch-up. Opportunities aren’t just for the business elite anymore; they’re available to everyone willing to do the legwork to find them.
Take a step back and look around your industry – what have you missed that could propel your business forward? Is there a networking group where you can make better connections? Trust is a huge deciding factor in building business relationships, and folks prefer working with someone they know or who’s recommended over strangers online. Are there professional directories that can boost your domain authority through backlinks? Are there grants that might ease the burden of paid ads or help you hire that copywriter or SEO expert, boosting your reach like never before? I get it – it’s often easier to stick to what you know, what you’ve perfected, and “stay in that lane,” even if you’re not moving forward. But look at those who took a chance on the shoulder. They saw an opportunity and got ahead because they were willing to risk it possibly working out. Just to be clear – not condoning breaking traffic laws! Not sure why, but felt like that needed to be stated.
Lesson Three: Helping Others
For those who live here, have you ever needed to merge into a lane with space for your car, but the moment you turn on that blinker, it signals everyone to go bumper-to-bumper so you can’t get over? It’s almost comical how often this happens. You can even hear the roar of the engine when someone speeds up just to block you! Even though I shake my head at the absurdity, I appreciate the lesson in it. While business owners, by the basic definition of a SWOT analysis, are in competition (i.e., T=Threat), finding those we can connect and network with – and if we’re lucky, those who complement our business for partnerships and collaborations – benefits us all.
We don’t need to step on others to be more successful, to get higher, to be better. I applaud those who constantly reach back during their journey to success and pull others upward. There are so many ways fellow entrepreneurs can help one another: speak their name when they’re not in the room, send referrals their way, do bundles together to bring your audiences together (perfect if your businesses complement each other – like a copywriter and web designer), or just be on the lookout for one another. Don’t trash talk, belittle, or demean the competition to get ahead; it doesn’t reflect well on you. We all work differently, with key strengths and weaknesses, and only know as much of each other as we choose to reveal. Be kind (there’s that word again) and lend a hand when you can.
Lesson Four: Learn to Pivot
If there’s one thing guaranteed on 495 or 93 on a Friday, it’s an accident. Coming out of Boston on the day this post was inspired, there were several. What should have been a 40-50 minute drive turned into 1.5 hours because one accident led to a redirect, which somehow led to another accident. As mentioned above, this is where planning ahead comes in, but sometimes even the best plans can’t anticipate the unexpected. In those moments, the key is to pivot. You already know what you can’t do – now, what can you do? The definition of insanity is doing the same thing over and over again but expecting a different result. In business, we tend to do just that. We keep writing blog posts but can’t figure out why our organic traffic isn’t increasing. We keep pouring money into Facebook Ads and get frustrated when that traffic doesn’t convert to leads. We book consultation after consultation but can’t understand why potential clients vanish.
The problem is we keep repeating the same processes without looking at the data. We aren’t taking a bird’s-eye view of the situation, considering our wins and losses, and adjusting our processes to succeed.
With Facebook Ads, are you doing A/B testing to see how your messages and images connect with your audience? Are you evaluating the reception of your product or service by tracking opt-ins (with UTM – i.e., link tracking) and/or calls generated by including a “how did you find us” on your sign-up forms? With consultations, are you placing potential leads in a CRM to ensure you’re monitoring them through your sales pipeline, sending follow-up emails to keep your business top of mind? Have you set up automation for this – a timely email here, an SMS nudge there, so it’s not just another thing on your to-do list?
Take a moment to step back from your business and see where you’re thriving and where you’re floundering. Don’t view it as a failure but as motivation to pivot your process. Very important: don’t make a slew of changes at once, as it’s hard to evaluate what’s working and what’s not. Create a spreadsheet of proposed changes, with columns to track before and after implementation, and lists of what changes come to mind (more/less emails in follow-up campaigns, adding/removing Hero video from the website, more/less variations of Facebook Ads). Remember, data is your best friend, so if you haven’t added Google Analytics to your site, now is the time. I also recommend setting up the Facebook Pixel, even if you aren’t currently running (or have never run) Facebook Ads. You can’t retroactively track that data, so even if it’s years before you run a Facebook Ad, you’ll be grateful for the data that pixel collected to create Look-Alike Audiences from past visitors (i.e., demographic information and target audience analysis that most businesses would love to have right at your fingertips).
Lesson Five: Determination
Last but not least, this is actually a callback to Lesson Three. As mentioned before, when trying to merge into a lane here, you either have to be patient and wait for someone to finally let you over, or be determined and put the nose (the front end of your car) into the lane with the hope and prayer that your “aggressive” move doesn’t lead to honking horns, flying fingers, or an accident. As entrepreneurs and small business owners, we know owning a business is not for the faint of heart; we understand the number of hours that go into it daily. We don’t know evenings off, weekends free, or leaving it at the door. Our business is part of us; it goes everywhere with us. We wake up thinking about it; we go to sleep thinking about it. Its wins are our wins, and its failures are our crosses to bear. For this reason, we are driven to give our businesses our all. We don’t know the outcome; we don’t know if hard work and patience will pay off or if it will all come crashing down. What we do know is that we are the fire in its belly, and as long as we work hard and burn bright, the beast will keep going. Yes, we need to keep balance in mind (burnout is no joke), but balance doesn’t need to diminish drive and determination. Why do you think the phrase “Work Hard, Play Hard” exists? There will be moments when we question why we are doing this, is it worth it, what’s the point (if it hasn’t crossed your mind, it will – give it time), but keeping our “Why” in mind is what fuels our determination. Never forget that failure is part of the process, disappointment is part of the process, and all are necessary to keep us driven. If it all came easy, would we appreciate it as much? Would the wins be as sweet?
While each day on the road feels like I’m taking my life into my own hands (I’m exaggerating – it isn’t that bad…most days!), driving in Massachusetts has surprisingly offered unique perspectives on running a business. Take some time to look at your own environment – how can you translate the day-to-day into lessons for your business? What can you learn from how people in your area drive and interact with one another? Insight can come from the most unlikely places, bringing motivation and reminders. Allow your surroundings the opportunity to teach you; you might be surprised at what you learn.
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