Yesterday I was chatting with my friends as usual on Zoom. We were talking a bit about business and how we'll overcome the crisis. Looks like many of us will have to improve our chops if we're to stay competitive and reach new clients.

As we were talking about decisions we made, a thought-provoking question popped up:

What do you regret doing at the beginning of your business venture?

It took us quite a few minutes to ponder the idea.

What are my actual regrets?

I'm not a could've-should've type of person. I care about the present moment. Even if I regret something, it's useless because I can't change the past.

So why bothering in the first place to think about it?

If I had a time machine...

That's what I asked. What if I had a time machine?

Alarm clock with hand
Photo by Lukas Blazek / Unsplash

Besides asking that girl out 15 years ago, I felt there are many things I'd do the other way around in business.

Although you can't change the past, every next venture you start is easier because you know what to avoid.

Besides, you can give practical advice to novice small-business owners and help them survive the first year. No, seriously. If someone had told me the things I'm about to share, that would've spiraled me forward like a rocket.

I found this little thought experiment really interesting. So I sat down, and before writing this article, I did two things:

  • I took my notebook and made a list of regrets. Basically, a list of things I'd change if I had a time machine. There isn't a better way to share experience then starting from a personal story.
  • I did my research on Facebook in various groups. I wanted to find out what real people with real problems in real life have to say.

The internet is full of fluffy, cliche articles. My first sentence was BS like "I'd show more bravery" or whatever... /sigh/

No, if I'm going to do this, it must be honest and raw.

So here's my list. Honest and raw.

Things I regret doing when I started my small-business venture

  1. Hiring my best friend to work with me.

It's fun hanging out with certain people, but business is business. Relationships often get screwed up.

Hint: If you're considering hiring a friend, try giving them a trial period for adjusting purposes.

2. Not having any organizational structure

Even tho I had 10+ people in a team. First stressful project and we were all going haywire.

Hint: Hire someone to make an organizational plan for you. Saves time, money, and a plenty of headaches.

3. Not writing things down

Gosh, it makes things easier when proving a point.

Write everything down. If you're often having video meetings with your clients, record them. Or send a summary in an email.

No he said she said afterwards.

Writing a business list in a notebook
Photo by Cathryn Lavery / Unsplash

4. Never telling No to my clients.

Absolutely, Karen, we can change the whole design based on your 7 year old son's feedback.

A client is almost always right. Sometimes they don't know what they need. It's your job to help them, but without sacrificing your reputation.

5. Setting no boundaries between personal and business life

Sure, it's 2 in the morning, pitch me on Whats-app, no prob.

Nope. Set office hours. Take care of yourself.

6. Not hiring enough highly-skilled people

I mean, why hire seniors when juniors cost less, right? Skilled people are your investment in the future of your company.

7. Putting up with micromanagement

It's just too much pressure for everyone involved. Build trust from the start. Work with reliable people.

8. Lack of any kind of management

Yeah, I get it, reports are boring. It's even more boring to track where things went wrong if there aren't any clues.

9. Not checking whether everyone agrees with a project goal

No, it's not O.K. to have 10 people working on your project and everyone having completely different picture of what the project is or should be. An aligned vision Β is a recipe for success

Quite a list, huh?

Now, I did a little research and compared experiences with other people.

15 small-business owners and their biggest, no BS regrets from the trenches

small local business, an older man, owner of the shop, looking at the photo
Photo by Alev Takil / Unsplash

Answers are from various Facebook groups for small-business owners. As far as I can tell, regrets do not differ much. It seems we all go through the same path.

Blaming everyone but yourself

comment from a facebook group for entrepreneurs and small business owners, on blaming everyone but yourself

We've all been there. Giving our best every day, struggling to keep everything under control, pulling our weight every time when we're supposed to... Then sh*t happens.

And it's hard to accept that all that effort just wasn't enough at the moment.

Own up to it. This will help you build a strong personality.

Managing cash flow

comment from a facebook group for entrepreneurs and small business owners, on poorly managing of finances

The thing about public education today is that they teach you how to do complex algebra, but after you graduate, you aren't quite sure how to pay your bills.

A guy who left this comment obviously risked his first business venture too much, had to close and open another one.

Not having a good business plan

comment from a facebook group for entrepreneurs and small business owners, on not having a business plan

This sounds like a no-brainer. Yet, it is if you're a seasoned professional or you've worked in big companies before. A lot of people out there just skip this step.

No budget to hire a consultant. No time to even think about it. Let's start a business and solve things on the go.

Unfortunately, it doesn't work that way. A good business plan is a prerequisite for doing serious business.

Without it, you're just sailing across uncharted seas, hoping to stumble upon a land.

Not doing research

comment from a facebook group for entrepreneurs and small business owners, on not doing research and just asking friends

Now, I'm sure your friends mean well. But unless they're doing the same job as you do or working in a analyst department somewhere, you should be doing your due diligence. Β 

  • Test the market.
  • Do surveys.
  • Poll people on Facebook.
  • Talk to customers.
  • Ask for reviews and feedback.
  • Check what you're competitors are doing.

Not valuing yourself enough

comment from a facebook group for entrepreneurs and small business owners, on not valuing yourself enough

If I had a dime every time I heard this, I would've been Bezos right now.

No one is going to respect you if you don't respect yourself first. You're a professional.

Act like one.

a shop window with three sales stickers
Photo by Artem Beliaikin / Unsplash

Giving (too many) discounts

comment from a facebook group for entrepreneurs and small business owners, on giving discounts

Discounts are a viable marketing tactic. They drive sales.

However, giving out too many discounts could make your customers get used to lower prices.

The moment you put a higher price, your sales might plummet because people don't perceive your offer as valuable.

When giving discounts, do it less frequently. Do short-term flash sales. Give coupons to loyal customers. If you're giving them to everyone and every day, it loses value.

Build your brand on various channels online and offline. Avoid the discount trap.

Staying stuck on Yellow Pages

comment from a facebook group for entrepreneurs and small business owners, on putting an ad  for small business on yellow pages

You've put your ad in the Yellow Pages and now you're sitting at your desk, quietly sipping your drink, reading newspaper and waiting for your ship to come in.

No.

Being proactive is a state of mind.

First rule of business is: Always be prospecting.

Reading recommendation: You might be interested in our article on 12 ways to do marketing for free during the Corona crisis (applicable also in this post-pandemic world).

Wrong assumptions

comment from a facebook group for entrepreneurs and small business owners, on making false assumptions

Always double-check. Not everyone thinks or behaves the way you do. Relying on someone else's moral compass is risky.

No savings

comment from a facebook group for entrepreneurs and small business owners, on not saving

There's no bulletproof way to start a business, yet there are thing you could do to be prepared and avoid risks.

Savings can be your fuel, keep you afloat until you start making steady sales.

Jack of all trades, master of none

comment from a facebook group for entrepreneurs and small business owners, on being a jack of all trades, master of none

Sorry, you just can't (and shouldn't) carry the weight of the world on your shoulders.

  • Build solid relationships.
  • Know your strengths and weaknesses.
  • Focus on one thing.

Bad hires

comment from a facebook group for entrepreneurs and small business owners, on hiring people with whom you have close relationships

Been there as well.

Hired a close friend. Didn't end up well.

I'm not saying you should avoid hiring any friends all together. Just think it through. Relationships often get screwed up.

Working for peanuts

comment from a facebook group for entrepreneurs and small business owners, on working for free

"You know, Garry Vee said that..."

Give me a break. πŸ™„ Yeah, he said you should back your ambition by doing a bit for free until you get enough traction... Or whatever.

Which is fine if you're a college grad and you're trying to land your first gigs. If you're trying to pay your taxes, working for free won't help.

Charge minimum rates. But do charge, don't work for free. Otherwise, people will just assume your services aren't worth it when you do try to charge.

Self-doubt

comment from a facebook group for entrepreneurs and small business owners, on doubting oneself

Impostor syndrome is actually quite common.

But bear one thing in mind: you wouldn't make it so far if you were a bad professional.

Business has its ups and downs. Learn to cherish fine moments and endure bad ones.

Ego is your enemy

comment from a facebook group for entrepreneurs and small business owners, on having a huge ego

Pics on Instagram with expensive cars, in shiny suits, at breathtaking locations, pretentious hashtags...

Admit it, you follow a couple of those attention-seekers as well. Unfortunately, they invest too much time in personal branding that they forget the reason they started doing it.

Yes, personal branding is important, but don't forget – no marketing can sell a bad product or service.

Striving for perfection

comment from a facebook group for entrepreneurs and small business owners, on striving for perfection

Nobody is perfect. And no one expects from you to be perfect. In fact, you might be the only person who thinks you should be perfect.

You'll make errors. Receive awesome testimonials. Get a few angry calls here and there from customers.

It's fine. (Sh)it happens.

What about you?

What do you think about these regrets?

Is there something you regret? Or, if you're at the beginning, do you recognize your struggles in these examples?

Please, share with me, I'll be happy to discuss more about this, as my goal is to help small-business owners around the world to improve their businesses.