If You Feel Stupid “Doing the Work,” You’re in the Critical Weed-Out Phase | by Rachel Greenberg | Mar, 2023

Conquering it will put you above 80% of the competition

If you feel stupid “doing the work”, you just may be in the critical weed-out phase. This phase alone is what seals many entrepreneurs’ fates, and conquering it will already put you above 80% of the competition.
Photo by Harps Joseph on Unsplash

Before I started my first company, I had a vague idea of what the “day in the life” of a successful entrepreneur should look like. That stereotypical vision was a Silicon Vallified agenda, not too different from what you’ve seen in countless startup documentaries:

Ironically, when you’re actually building a brand-new product, service, venture, or business expansion, very little (if any) of your time may be comprised of those aforementioned tasks.

If I compare a “day in my life” today to my first few years of attempting the “entrepreneurial life”, it’s embarrassing how starkly different they really are and even more mortifying to know what really moves the needle — and what never did. If you’re wondering if you’re doing the “wrong thing” or spending your time on shamefully low-value tasks and making a mockery of your startup journey, read on to uncover where the real value lies.

If you entered the startup world — or are entering it — with the assumption that there’s some secret line or qualification separating the experts from the meanderers, you may be surprised and disappointed to know the truth. The difference between the two is often twofold:

  1. Reps
  2. Confidence

Occasionally — and in certain fields, like healthcare — those “experts” may also have degrees, certificates, or other formal credentials giving them a significant edge over a DIY newbie. However, more times than not, the point at which someone deems themself enough of an “expert” or professional to release their product or service to the world is a matter of confidence-based opinion. That confidence and expertise can often be achieved through conquering #1: Reps (repetition), which comes from good, old-fashioned time at the grindstone.

Furthermore, the majority of the revenue my businesses have made has come from the “stupid work” I did myself, even when I didn’t consider myself an expert or professional. For example:

  • I’ve spent more money than I care to admit over the years outsourcing marketing, content creation, website and app development, etc.
  • Still, the vast majority of the money my ventures have made has been a direct result of marketing I did myself, content I created, and even websites and tech apps I’ve largely built…

So, what is a justifiable day in the life of an entrepreneur?

Sometimes, a day in my life looks like writing months’ worth of marketing emails — even though I’m not a “marketer”. Other times, it looks like building tech platforms — even though I’m not a “technical founder or developer”. Sometimes it looks like painstakingly building a brand-new, so far unreleased product or piece of content for one of my ventures, even though I could hire a handful of experts to collectively build it for me.

Perhaps I skew far to the side of DIY-ing my way through my entrepreneurial journey, and there are definitely days I ask myself if I’m doing the “right thing”, but the truth is, the right thing isn’t always sexy enough for a TechCrunch feature, Hulu series, or HBO documentary.

Do you want to watch a documentary of a founder planning out 57 marketing emails, laying out picture book lead magnets, or watching a development tutorial as they plan to build a new platform? Probably not — at least not for more than a few seconds. Therefore, since some of the not-so-glamorous, behind-the-scenes, far-from-Instagramable work feels tedious and underpublicized in the startup world, it’s easy to assume we’re doing the wrong thing. It’s easy to ask yourself is it stupid that I’m spending my time on XYZ?.

The answer is simple: If you ask the right person, you’ll get the right answer; if you ask the wrong person, you won’t.

I asked a friend and a fellow entrepreneur who’s seen a large portion of my entrepreneurial journey — who met me before I’d launched some of my biggest projects — this very question about a current pursuit that was bruising my ego. It was bruising my ego because shamefully, it felt “below my paygrade”. It’s not that I felt too smart or too good for this activity; I simply felt that most of my peers would look down upon it — which is the very reason I believe it represents a great opportunity (an overlooked gap in the market with significant whitespace to fill that’s perfectly synergistic with multiple of my other ventures).

When I asked my friend this question, her response wasn’t just reassuring; it was unequivocally true. She said: “I think that’s how it always feels at the beginning of building a new thing — that’s kind of what it’s like to be an entrepreneur.”

I had spent so much time working on more mature projects and tried and true proven tasks and strategies that I’d nearly forgotten that every venture I’ve ever built required this stage. In fact, it’s this stage — the stage of building in silence, with minimal feedback or financial reinforcement — that weeds out countless entrepreneurs who can’t hang with the uncertainty.

If I were writing marketing emails, I wouldn’t have thought twice, since I’ve seen them pan out. Even if one tanks, the task itself has still proven its value time and again for years, and thus has earned its place as a worthy use of my time. The same goes for building certain products or platforms. This new endeavor, however, is one I haven’t previously launched (though it’s been on the likely to-do list for years), so it’s felt harder to justify.

That said, just because an activity sounds less important, less TechCrunchable, and less Silicon Valley-ish than prepping a pitch deck for funding you don’t actually need doesn’t mean it won’t yield an outsized ROI. If anything, the most impressive ROIs I’ve experienced came from the least sexy, least impressive-sounding tasks I’ve done.

Truth be told, much of the work I did early on — and to which many aspiring newbie entrepreneurs (and wantrepreneurs) devote countless hours — is the real stupid work, and it’s largely based on egos and false premises.

I’m talking about slaving over a pitch deck, perfecting the most granular financial model with five-year projections and toggles for countless pipeline products, and crafting poetic founder bios on every startup networking platform out there.

If you’re spending more time building financial models than making them come true by pounding the pavement to acquire those customers, you’re probably doing the “stupid work” that feels “smart” or impressive. It’s not. No, it isn’t glamorous to send hundreds of DMs, thousands of emails, or cold call prospects begging for a beta customer, partner, or a sale. However, those are the actions that move the needle, and as a founder, they definitely aren’t below you.

If you’re prioritizing chasing fundraising or socializing in startup-centric founder or investor circles rather than building your product or service, once again, you’re doing “stupid work” that feels or sounds smart and impressive, even though it’s severely misguided.

Long story short, stupid work is the work you do in case someone is looking. Smart work is the work you do in spite of the fact that no one is looking, yet you strongly believe it fits into your company’s plans for future success.

My least impressive-looking days easily generate far more revenue than my most impressive-sounding ones, and at the end of the day, it’s only my ego that needs to take a backseat and pipe down as I trudge forward, feeling dumb for my unimpressive to-do list.

The false premise here that’s leading countless founders astray is the idea that there is a right and impressive to-do list or “day in the life” of an early-stage, first-time, soon-to-be-successful founder. There isn’t, and building a startup isn’t performative art for an audience; it’s the behind-the-scenes drudgery that no one would believe brings ideas to life. If it were certain, fun, and glamorous, everyone would do it; it isn’t, and thus, most don’t.

Founders who’ve white-knuckled their way through the not-so-glamorous, uncertain, tedious early stages of building a business from scratch do have a few secret weapons under their belt. One is the unwavering conviction in their mission and the belief that by out-committing their competitors and peers, they’ll already leave 80% of the competition behind.

These founders know that if they keep their heads down and do what feels like “stupid work” long enough, their peers’ faith will wane, confidence will shatter, and egos will convince them to drop like flies, disqualifying them from the race that doesn’t look how they imagined. To some degree, startup success is a game of stamina, willpower, and pain tolerance, and the entrepreneurs who can last the longest without the applause, glamor, or external reinforcement may emerge the strongest long-term victors.

So yes, you should objectively assess your daily actions to determine and confirm if they continue to align with your business-building strategy. But no, you shouldn’t assume hands-on, DIY projects or tedious tasks are “stupid work” to be outsourced or abandoned. “Stupid work” just may be the key to your entrepreneurial edge and the secret weapon to success.

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