Follow The Rules, Break The Rules, Or Make Your Own Rules?

Feb 25, 2021 | Growth, Mindset & Identity

I could sum up the existential journey of most business owners like so:

Make it up as you go. Learn the rules. Break the rules. Make your own rules.

Our culture and economy organize around rules. In school, we learn the rules (both explicit and implicit) so that we can excel. When we start working, we learn a new set of (related) rules so that we can fit in and work toward a promotion.

In Can’t Even: How Millennials Became The Burnout Generation, Anne Helen Petersen writes, “…success hinges on a student’s ability to adhere to a narrow understanding of ‘successful’ behaviors: getting good grades, performing well on standardized testing, behaving ‘appropriately’ and deferentially toward teachers, establishing ‘normal’ social bonds with peers, and being willing to participate in physical education.”

Our obsession with “the rules” starts early.

We make the connection between success & rule-following early, too.

There are also rules (often unspoken) based on your gender, class, race, ability, sexuality, or age—and if you defy those rules, you risk becoming a pariah. But, of course, following those rules brings its own challenges, too.

That brings me back to the journey—and relationship with “the rules”—of most business owners. Let me break it down phase by phase.

Make it up as you go.

Most of us (myself included) start out without the foggiest idea of what we’re “supposed” to be doing as business owners. We just know that we’ve got something (our time, a skill, an idea) that’s valuable and we can sell it in various ways.

We experiment a lot. We’re accepting of mistakes. And we start to figure some stuff out.

This is a really valuable phase. And it’s one that’s often really underestimated in terms of its power to teach us about our businesses and ourselves. That’s what leads us into the next phase…

Learn the rules.

At some point, we start to realize that maybe there’s a better way to do the things we’ve been experimenting with. This might happen very early on or it might feel like it comes relatively late.

We take courses, hire coaches, read books. We learn about all the things we’ve been doing wrong and what we should be doing instead.

It’s when all of that conditioning we have from school and traditional work environments starts to override the creative risks we’ve been taking.

Now, I’m not antagonistic to this phase. I think there’s plenty of value in learning from experts and there are certainly plenty of valuable frameworks and strategies that can provide the foundation for a more effective approach to business-building.

But as time goes on, many people get fed up with “the rules” and remind themselves that they got into business to forge their own path.

Which leads to the next phase…

Break the rules.

At this stage, business owners sort of give the middle finger to everything they’ve learned and decide to make it up as they go again.

This is often done with a flourish! But can also take the form of a “crash and burn.”

Sometimes business owners take a lot of pride in breaking the rules, while others do it sheepishly.

Now this is where a lot of small business owners stay. They’ve conflated systems, strategy, and making plans with following the rules—and so they’ve let that all slide.

So while they might be glad to be rid of the tyranny of shoulds & supposed-tos, they’re also a little stuck in a less-than-effective way of running their businesses.

Breaking the rules is probably a necessary phase to move through for most people. I think we need to be reminded that a healthy part of business-building is making it up as you go and finding your own unique way of doing things. Besides, a lot of business owners do better making it up as they go than following someone else’s system.

But breaking the rules isn’t sustainable. It serves its purpose for a time and then we need to move on from it or risk burnout from constantly reinventing the wheel.

Make your own rules.

The last—and most sustainable—phase of the journey is the one in which you make your own rules.

It’s where you take everything you learned—from making it up as you go, from the proven frameworks, and from your time breaking the rules—and start to build your own systems, set your own strategy, and make your own plans.

You set humane business policies and get serious about the financial situation of your business. You look at your business operations with an eye toward longevity. And you look at your vision with an eye toward legacy.

I suppose in many ways…

…you grow up.

Your confidence grows. Your willingness to take crap from other people diminishes. You may or may not be hitting all of the goals you set—but you feel like, given time, you’re getting there.

Every single stage has value.

Every phase of this journey has something to teach us. One stage isn’t better than another. It doesn’t mean you’re more or less of an entrepreneur if you’re in a particular phase.

It’s just that each phase has its particular flavor—and I think it’s helpful to know where you’re at and what’s next.

Now, it probably comes as no surprise to you that the business owners I enjoy working with and building tools for the most are in the “make your own rules” phase.

I like to let people to their own devices in the “make it up” phase because I truly believe that flailing your way through it is good and valuable.

I don’t have rules or proven frameworks to offer, so I don’t really create things that the “learn the rules” phase folks want.

And while I know plenty of people in the “break the rules” phase, I see my job as helping to guide people out of it!

But folks in the “make your own rules” phase lack the nervous energy, quest for certainty, or contrarian vibe that often comes along with the other phases. They’re ready to put in the work, think creatively and critically, and collaborate. Their attitude and burgeoning confidence set the stage for so much growth—personally, professionally, and in the business.

Do forgive me if I describe that group with deep love and admiration!

The unfortunate part of the “make your own rules” phase is that it can be lonely.

When you’re making it up as you go or breaking the rules, you’re so focused on your own stuff that you don’t really notice if there’s no one around to support you. If you’re learning the rules, you have the connections you gain from affinity with a particular system or coach.

But when you’re making your own rules, though, it feels like you’re on your own—even though you’re primed for collaboration. You’re looking for constructive criticism and constructive encouragement. But good feedback and the people who can give it are hard to find. The absence of support can be really palpable.

It can also be a real challenge to even admit that you have needs, to request support. Maybe you’ve worked hard to be perceived as someone who has it all together. Or, you might have been burned before. Maybe you grew up in an environment where asking for help was frowned upon or downright dangerous.

When you’re making your own rules, it’s key to:

  • Cultivate close relationships with colleagues, peers, or even mentors
  • Build connections prioritizing trust and mutual benefit
  • Disrupt your habits of trying to figure it all out yourself
  • Have a plan for asking for support before you need it
  • Identify the type of support you want—feedback, brainstorming, encouragement, processing, experience, advice, etc…—so you know how to look for it

With a healthy support network, you can make your own rules sustainably and effectively. You can do business your way and still have the systems, strategy, and plans that make your business stronger.

Making your own rules doesn’t have to mean you’re on your own.

If you’re up for making your own rules, we’d love to get to know you inside The What Works Network.

We’re accepting new members into our community through March 1—and it’s the perfect time to join because you’ll get in on our Spring bundle: a ticket to our March virtual conference ($199 value), early access to our newest program, SUBTLE ($199 value), and, of course, The Stronger Business Playbook, The Deep Dive, and The Community, too.


Host of What Works

Tara is a podcaster, small business community leader, strategist, and speaker. She’s been helping small business owners build stronger businesses for over a decade.  

Tara McMullin, What Works Weekly Newsletter

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