I eff-ed up…so, would I do it again?

It would be nice to think that the many years of schooling required to get most people to their first real job, plus the ~two decades of watching others’ mess up and have to learn things the hard way would be enough to prepare US, “the NEW generation” for success right out of the gate, right?

Sure, that would be nice. But that wouldn’t be reality. The truth that few people, particularly students, seem to realize as they advance through the traditional schooling system, is the fact that school is not the precursor to freedom. School does not prepare most people to become a founder or CEO, and in many cases, it may not even prepare them to become a good employee.

Take it from me, someone who also had make those mistakes firsthand, someone who had to learn the HARD WAY, the painful way, and possibly worst of all, the expensive way.

Now, because I don’t have time to write a Harry Potter-length novel, and you likely don’t have the patience to listen to me read through one, I’m not going to cover EVERY mistake I’ve made…there are far too many. But I will cover some of the most poignant and impactful ones.

Let’s break this up into three groups: Employee Mistakes, Entrepreneurial Mistakes, and Miscellaneous Mistakes (because goodness knows I’ve made some of those, as well)

Employee Mistakes:
I don’t want to say I was an awful employee (we’ll get into that in another blog), but I can definitely say I was an insecure one. You could call it non-confident, timid, intimidated, scared out of my mind, unsure, self-doubting, etc., and the list goes on. Point being, I did NOT instill confidence in my boss, our company’s clients, or likely anyone around me. I’m not saying I was quaking in fear all the time…but I won’t say I wasn’t.

Is a little humility in the workplace a bad thing? No, not at all. However, when your boss relies on you for soon-to-be client-facing tasks and deliverables, a little confidence (or at least an absence of fear) would be a nice thing. Why? It’s kind of like what happened in the great toilet paper hoarding of 2020, also known as the beginning of the pandemic. Some genius decided barricading him or herself inside a toilet paper castle would be the key to surviving this virus. If it were just that ONE genius, we could have called him “eccentric”, made a meme out of him, got a few laughs, and moved on…wouldn’t that have been nice? Unfortunately, it wasn’t just one genius. It was a “genius” leading a pack of other wannabe geniuses who decided to follow suit, since clearly toilet paper was the answer to eternal health and longevity. And such began the toilet paper hoarding, price gauging, and eventual shortage of 2020.

What’s my point here? It only takes ONE “genius” (or maybe “not-so-genius”) with an idea to misdirect the whole darn bunch. In other words, one person’s attitude, actions, or in my case, lack of confidence, can actually permeate throughout an entire group, company, or industry. That’s exactly why my personal insecurity (not thinking I was “smart enough” to do a good job in my grown-up finance job) resulted in my bosses second-guessing me…and possibly their bosses second-guessing them, and so on. Luckily, nothing made it that far up the chain of second-guessing, since you don’t typically pass a financial model off to a managing director or a client without having quadruple-checked it a few times along the way. Nonetheless, you can see why my insecurity wasn’t exactly a value-add in the workplace. If I couldn’t trust MYSELF to produce a good work product, why should my boss trust me? And if my boss can’t trust me, then I guess he better redo the whole thing himself, before showing it to his boss…which begs the question, why am I even here?

They say, in accounting, “Cash is King”; well, I believe in employment, “Confidence is King.” You don’t have to be perfect, and I do believe in owning up to your mistakes if you make them, but living and working in debilitating trepidation, simply because you feel scared or unworthy of the job you’ve been given really won’t help anyone. If you’re too afraid to give the presentation? Move over, someone else will do. If you’re too worried the financial report is wrong? Step aside, there’s another hungry applicant who will happily check that report, clean it up, and hand it to your associate. If you don’t believe in your own abilities at least as much as the person who offered you the job, shook your hand, and gave you an $X-figure salary agreement from day one, then maybe you aren’t ready to enter the workforce. Maybe you have some more soul-searching or self-improvement to do. Either way, your attitude, the way you present yourself professionally, and what you project among your peers and higher-ups is YOUR CHOICE. It’s only yours to lose.

Entrepreneurial Mistakes:
Oh, entrepreneurship, the land of daily challenges, heart-stopping horror stories, countless catastrophic failures, and a winding road of mistakes you’ll make as far as the eye can see. Here’s the thing about making mistakes as an entrepreneur, as compared to mistakes as an employee: as an entrepreneur, it’s your company to lose, and it’s YOUR money/time/career/product/team, etc. on the line. In other words, mistakes in entrepreneurship may be some of the highest-stakes mistakes you’ll ever make.

Where should I start? The time I overpaid for a tech product by an ill-equipped team, to the tune of $70k+? The time I launched a product with NO MARKETING PLAN, assuming my partners would 100% take care of that for me, simply because it was implied in their contract and they had the audience and resources to back it up? The time I got scammed by a brand-new ad team and let them play “experiment” (i.e. attempt to figure out what they were doing) with tens of thousands of my marketing dollars for three months? Oh, the list goes on…

Rather than go through each individual mistake, since we’d be here all day and I would end up crying over the hundreds of thousands of dollars of spilled milk in poor decisions and the consequences of “not knowing what you don’t know,” I’ll just highlight a few big areas to watch out for and some tips on how to avoid those incredibly frustrating, painful, and expensive mistakes.

Tip 1: Don’t outsource YET. Just don’t. Learn to do it YOURSELF before you delegate a thing. I’m talking about everything. I don’t care if that means you’re staying up till 3 am every morning reading a book on “how to code a launch page” or if you’re watching hours of tutorials on “how to manage a digital marketing ad campaign on X platform.” I don’t care if after all that, all you come away with is a one-page pink website with a big blue smiley-face in the middle, just like one of my good friends and great founder and CEO, Taylor did, when he was attempting to rebuild his company’s website and app…(after overpaying ~$25k for an under-qualified team who messed it up, of course). You see, it really doesn’t matter if you aren’t great, or even good, at the tasks you’re looking to outsource. All that matters is that you’ve learned, you’ve tried, and you know what’s entailed. THAT is how you know exactly who you should be hiring, what’s a fair timeline to project completion, and what’s a fair price for a qualified person to get the job done.

Tip 2: MARKETING, MARKETING, MARKETING. Listen, I’ve been one of those finance snobs before, who looked down on marketing activities as “fluff”, fun, unnecessary, low value-add, non-revenue-generating B.S. But, guess who’s laughing all the way to the bank? NOT ME. The smart entrepreneurs who knew that marketing is truly the lifeblood of sales, the singular most important thing to keep the company going, and the one and most important revenue-generating activity out there. If you don’t know, care about, invest in, or spend some real time on marketing, you better hope and pray for some viral media and PR, because without that, some great marketing, rapid-fire word-of-mouth, or pure magic, you’re dead in the water, as far as sales are concerned.

Tip 3: This kind of goes along with number two, but just remember, if you build it, and that’s ALL you do, 9.9999999 times out 10, they WON’T come. NO ONE will come. Nothing will happen. And you’ll join the hundreds of thousands or millions of other wantrepreneurs who had a great idea, put it out there, and launched to crickets, chirping away, but failing to open their little cricket wallets and hand you so much as a dime.

Tip 4: SAVE. YOUR. MONEY. We’ll get into this more in the miscellaneous mistakes, but the long and the short of it is the fact that building a company and marketing a product or service will almost always be far more expensive than you imagined. Trust me, that thing you didn’t know you needed? You’ll need. That other thing you’ve never even heard of? You’ll need that, too. That random last thing you thought you could skirt by without? Yeah, you can’t, so you can just add that onto the bank statement, as well. Startups can get expensive, but even with a tight budget, unforeseen expenses will most likely pop up here and there, and you want to provide yourself with enough cushion to address them before they cause even greater (and more expensive) problems down the line.

Miscellaneous Mistakes:
We all make tons of random mistakes all the time throughout our lives, but there are some, even in your personal life, that can have a detrimental effect on your professional or entrepreneurial career. Knowing which to watch out for ahead of time can save you grave damage to your and/or your company’s reputation and put you on a much faster path heading towards success, rather than hurling yourself at 120 mph towards a much less forgiving brick wall.

Not being professional. It might seem like it’s “just a school class” or “just an assembly” or “just a meet-and-greet.” Maybe it’s “just a mock pitch competition” or “just a practice interview.” Here’s the thing: its’ NEVER “just a XYZ.” It’s ALWAYS an opportunity, and you never know who you might encounter or what positive outcome might be lurking around the corner, but you’ll only find that out IF and ONLY IF you present yourself with your professional foot forward. I wish I could go back to college and business school and rethink some of those outfits, re-prepare for some of those meet-and-greets, and re-introduce myself as a young professional, even years before I became one.

All contacts are business contacts. Build and maintain your network ALL THE TIME. This kind of follows along the lines of the above, but in addition to being professional, you want to be cognizant of the fact that, as they say “your network is your net worth.” If you’re fortunate enough to rub elbows with like-minded, ambitious, aspiring people through either schooling, a job, summer programs, or professional or networking events, you want to be sure to create and cultivate those business relationships. It doesn’t matter if it’s Joe from AP calculus or Bonnie the financial analyst; one day, Joe might be running a tech firm looking for a co-founder or CEO, and Bonnie might be a venture capitalist, sourcing startups to pitch to her partners. You just never know who these people you meet will become, who they know, and how your paths may come to cross again, but if or when they do, you’ll sure thank yourself for having created and maintained such a valuable network and great asset to your entrepreneurial toolkit. Believe me, those well-thought-out thank you letters, following up on every business card exchanged, sending a personalized message and invite on LinkedIn, for the little time and effort those small tasks require, the potential for out-sized returns is always there, and like most things on this list, it’s YOUR opportunity to lose.

I realize this list wasn’t comprehensive, and I ended up going off on a few tangents here and there, which turned this failure story into more of an inspirational one; for that, I apologize. I’m sure I’ll go on to further elaborate on my many mistakes, pitfalls, and let’s be honest: failures, in other blogs and podcasts, but for now I hope you got your daily dose of advice, and that you can use this to do better, be better, and add to the next generation of successful entrepreneurs who get there faster than I did. Goodness knows our world could use it.

Rachel Greenberg