5 Clues You’re Building a Business to Imprison You, Rather Than Free You
No, entrepreneurship doesn’t have to mean being a slave to your startup. However, you can only blame yourself for what you’ve built.
When it comes to pet peeves, one of my biggest (though perhaps unwarranted) ones is when people are on their phones, far from present, delaying or disconnecting from “IRL” (in real life) experiences. While I can appreciate that the social media age is upon us and many people are connected to their phones, technology, and businesses 24/7, I’m someone who prides myself on living in the real world as much as possible…despite running a handful of digital companies.
In fact, my preference for real-world experiences over the metaverse-obsessed phone addicts who’d rather live in a screen has never held me back, precisely because I’ve purposefully built freedom and disconnection into my businesses. Well, to some degree. That said, I have a friend and aspiring entrepreneur who refuses to believe designing a freedom-enabling business is possible.
Instead, he’s fallen for every trap that’s begun to enslave him in a business that’s rapidly taking over his life — despite being far from profit. Here are five clues you may be building a startup that will succumb to a similar fate, along with the tips to avoid that and achieve a profitable venture that also allows you to be present “IRL”.
1. Lack of automation (or scalability)
Spoiler alert: The words “automation” and “scalability” are not reserved for high-tech startups backed by VCs requiring exponential growth and massive teams. Instead, automation (and the subsequent scalability it facilitates) is a crucial element to building a business that doesn’t suck — or suck the life out of its founder and team.
If you’re letting constant, repetitive, manual tasks compromise your time — especially on a daily basis or at inconvenient moments — I’d argue you’re letting your startup encroach upon your freedom in unnecessary ways. More importantly, I’d argue there are very simple, affordable solutions that you’d be remiss to ignore.
A few areas in which to implement automation:
- Content marketing creation, scheduling, and posting
- Lead generation for prospects’ first touchpoint
- Customer onboarding and confirmations
- Almost all mass or standard email, text, and chat communications
Where to avoid automation:
- High-tier (premium, expensive) and highly-customized services, order confirmations, and sales calls
- Fire drills (even if automation can handle these, a human touch goes a long way in peace of mind, customer experience, and resolution)
Investing a few hours in researching, learning, and implementing a few key automation software tools could make a jarring difference in your business operations and save you thousands of hours (and tedious headaches) down the road.
2. Failure to batch and pre-plan
A close cousin to automation is content batching and pre-planning, and no, I’m not just referring to social media marketing. For years, I’ve set aside weeks in which to plan, batch-create, and schedule months’ worth of marketing content and product launches. Yes, I’ve known three, six, and sometimes nine months out what we’re launching (for businesses that employ multiple annual product launches), and no, that hasn’t required any last-minute scrambling.
As a Type AAA person who believes most everything is plannable, I attribute last-minute scrambling to a major failure or blind spot in a company. In other words, if I’m working on something the day of (or even the week of), that screams poor planning and makes my blood boil. Why? Because in most cases, those last-minute scrambles are 100% preventable.
My friend, however, has convinced himself that it’s acceptable — and even prudent — to board a perpetual hamster wheel of daily and weekly tasks and requirements for which he can never get ahead. When I’ve proposed the idea of content batching and pre-planning (and shown him examples of successful founders in his industry who do just that), his retort has always been:
- “But I like doing [said business activity]”
- “But having a daily schedule keeps me disciplined”
- “But if I didn’t do this, what else would I be doing?”
To that, I’d reply: Sure, you might like (or not mind) doing a certain daily business task now, but once you’ve been running this venture for many months, years, or even decades, the tedium is likely to set in. Furthermore, you may like the option to do something, but the obligation is when your freedom gets compromised.
With respect to discipline, you don’t need an inefficient to-do list to keep you disciplined. You don’t get more brownie points for repeating the same activity if it isn’t the highest and best use of your time and effort. Profit doesn’t reward working harder or longer; it rewards adding the most value, and I believe you can add more value by building a pre-planned, scalable venture that isn’t bottlenecked by your 24 hours in a day.
As for the question of what else he’d be doing, that’s a great question that could open the door to new skill acquisition or expansion opportunities. However, one of the worst reasons to take on an inefficient task is because you don’t know how else to fill your time. As a founder, there are always countless opportunities to squeeze the most value out of your hours, and sometimes it takes weeks of deep research to figure them out, but avoiding the question is certainly not the best answer.
3. Belief that you’re irreplaceable
I’m going to be brutally honest here: I’ve met very few entrepreneurs who are truly irreplaceable to their startups. That said, I’ve met countless entrepreneurs who believe they are and thus, build a business that’s hindered by their shortcomings and nearly impossible to scale or sell.
In fact, this is where influencer-led companies tend to fall short (if they aren’t thoughtful and careful from an early stage). While some founders, like my friend, may believe that being the “face of” their venture is what will keep them valuable, I’ve more often seen it play out the opposite way.
To that end, I know multiple founders who’ve built successful 7+ and 8+ figure companies who’ve strategically stepped away from the forefront, brought in other faces, and distanced themselves from their brand in order to secure an exit. Why? Simple: Any business that requires a specific founder’s presence, association, or likeness in order to have success or customer appeal will require that founder’s respective involvement forever.
If you sell a business for which you’re an integral, irreplaceable puzzle piece, you better be one of the assets acquired in that transfer of ownership.
Since my friend believed he was irreplaceable, he made himself the prominent and sole face of his business. In so doing, he instantly cut off other opportunities, tied his hands in many ways, and tripled down on the lack of freedom his business would allow him. He clearly didn’t realize (or believe) it is possible to allow others to fill in for you, share the spotlight, and perhaps even attract more prospects who might resonate with a brand showcased by multiple diverse faces.
4. Distrust in your tools or team
I’ve built businesses with big teams, and I’ve built (sometimes even bigger) businesses with small teams, but there’s one commonality required for scalable, liberating success, no matter the size of your team: Trust. If you don’t trust the team you’ve hired and/or the tools you employ enough to run without your constant chaperoning or micromanaging, you’re significantly diminishing the benefits of employing that team and those tools at all.
Though my friend had hired a fragmented team to take on some of the grunt work in an effort to free up a bit of his time, he didn’t trust any of these team members with any critical tasks or autonomous roles. In other words, he’d delegate to them the small tasks (that could be more efficiently, effectively, and affordably accomplished with automation software), yet reserve the larger, strategic, needle-moving ones for himself.
While it may feel hard to let go of some of the control as a founder, it’s a crucial step in building a business that doesn’t burn you out. It can be scary to offload a critical task (like sales, marketing, or anything customer-facing), but once you see a team or a tool perform just as well as you, you realize you’ve built a valuable (and possibly sellable) asset, rather than a glorified job (or personal prison).
5. No succession, exit, or expansion planning
I’m not suggesting that every startup needs an exit; however, I am suggesting that founders who punt any thoughts of succession, exit strategy, or expansion planning might be too wrapped up in the day-to-day operations at the expense of the long-term broader vision. I’ve been there: I’ve been years into a venture, deep into the weeds of its operations and steady growth, only to realize the business had become more like my job than a separate asset I could easily (and lucratively) transfer.
Some founders cling to the excuse “But I’d never want to sell”, and while that’s fine, that doesn’t excuse unknowingly binding yourself to a venture forever with no future options. At the end of the day, each founder needs to ask themselves what they’re truly hoping to get out of the business:
- Is it a chance at financial freedom?
- Is it merely a fun way to monetize a hobby?
- Is it the pursuit of a lifelong passion with purpose over profits?
Any of those options could be the case, but I find that many founders who are caught up in the day-to-day minutiae have yet to consider the longer-term end-game. The last thing you want is your startup controlling you, dictating your future, rather than the other way around.
The price of freedom
So many wantrepreneurs and 9-to-5 employees would never underestimate the price of freedom. In their eyes — the eyes of people who have yet to build, launch, or grow their own business — entrepreneurship looks like freedom from the boss, the grind, and the daily obligations without end. Ironically, many of those freedom seekers swiftly change their tune and lose sight of why they ventured towards startup life in the first place once they’ve replaced one set of golden shackles for a pair of brass ones.
As you build your business, don’t discount the very pursuit that drew you to it in the first place. You’re either building freedom-enabling assets or freedom-inhibiting obligations; it’s up to you to know the difference and objectively admit which ship you’re captaining.