5 Mistakes I Made When Starting My Business (So You Don’t Have To)

Author: Jordan Fried

Jordan Fried

Jordan Fried

6 min. read

Updated October 29, 2023

It is daunting to start your own business—very daunting. There are a hundred and one things that can go wrong, and inevitably it will the thing that you’re least expecting.

To be honest, it doesn’t matter if you are starting up a business for the first time, or kicking off your latest venture; it doesn’t get less challenging. This is why advice from people who have gone through something similar can be both hugely helpful and crucially important.

I should know: I have started a few online ventures, the most recent of which has grown into a market-leading VPN site. But the road has not always been a smooth and straightforward one, and I am the first to admit that I have made a few mistakes along the way.

But if reading this helps you to avoid these five simple—yet costly—mistakes, then it will be a few minutes very well spent. So here is my run-down of the five biggest mistakes I made when starting my business (so you don’t have to make them too).

1. Micromanaging my team

When you start a new company, it is your baby, your focus, your everything, and this makes it very easy to get sucked in. This results in what is, in my view, one of the worst management techniques: micromanagement.

Of course, you want to know what is going on in your company and make sure everything is being done to your standards. But micromanagement is not the best way to do this, for a number of reasons.

  • It demotivates your staff
  • It makes projects take longer and run less smoothly
  • It drains you physically and emotionally

It is vital that you hire staff that you trust and believe in, and then leave them to get on with their job. Of course make sure they are reporting to you and keeping you abreast of developments, but don’t be looking over their shoulder all the time, or they will leave.

Plus, it will be harder for you to focus on the more important tasks that you actually need to do yourself.

2. Failing to keep a bird’s eye view of all employee workflow

No, this is not directly contradicting my first mistake. Micromanagement is ineffective, but it doesn’t mean you shouldn’t be monitoring the workflow of your staff and the progress they are making.

You need to have oversight, but you don’t need to be delving into the detail. I would suggest trying to use tools like Trello to facilitate workflow for staff in and out of the office. A project management system like this can help keep things simple and allows you to oversee progress while still giving staff the freedom they need to thrive.

Management systems also enable you to employ different managerial styles with different staff. Some team members will need more input from you, while others will benefit from you taking a step back. These services let you do both.

They also help staff to effectively manage their own workload, and you should also see a drop in the number of deadlines missed or projects delivered incorrectly. Just make sure your team has the right training to use the software effectively, then leave them to it.

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3. Wasting time on weekly meetings

I always used to think a weekly team meeting with staff members was essential. Direct engagement will make them feel important and part of the future of the business, I thought. Good for moral too, I thought.

Wrong! Weekly staff meetings quickly became a huge problem. They ate up far too much of my time, yet delivered precious little—and staff feedback also suggested most of them saw it as an unproductive half-hour.

Such formal meetings are completely unnecessary these days and I have scrapped them entirely. Open-plan offices mean I am engaging with all of my staff each day, and tools like iDoneThis allow users to take control of their own accountability and let me have input when needed.

For remote staff or those based in other offices, we now use numerous web chat services which can allow you to speak face-to-face with staff individually or collectively, from wherever they are. We use Slack for everyday chats, and Zoom for our monthly company calls (first Monday of each month).

Dragging off-site staff into the office for such meetings is just not necessary, and axing these meetings has freed up my time and actually improved my communication with my team.

4. Not renting my own office sooner

Working in the tech sphere, I initially decided that office space was unnecessary and an outmoded concept. I hired remote workers and thought online communication was sufficient. I couldn’t have been more wrong. It quickly became clear that while I didn’t need all my staff sitting in the same room every day of the week, I did need a central hub that the team had access to if and when they needed it.

Often, remote staff would come into the city for meetings with suppliers and customers. Without an office of our own, they could never host these meetings, which often proved not only costly in terms of transportation but also sometimes seemed like we were being rude.

Frequently, they would also need a place where they could work for a couple of hours in between meetings. My expense claims from Starbucks were sizable.

The clincher for me was when a member of my team was having building work done at her house. She couldn’t work there and instead had to sit in the corner of a noisy local coffee shop. She told me that commuting into the office for a couple of weeks would have suited her better and made her much more productive.

Having even a small, occasionally-used physical office is good practice and one of the best investment I have made to date.

5. Not implementing a “12 week year”

The “12 week year” has been essential in making a success of my businesses. If you haven’t come across it before, take a look at this site.

Essentially, it means breaking the year down into quarters. By doing this, we have managed to instill a greater sense of urgency and motivation in our staff through shorter deadlines and working windows.

It is more efficient administratively as well. We no longer have old-fashioned “annual reviews,” but instead more regular staff review and a development agenda which is beneficial to both staff and the business.

Moving over to the “12 week year” has proved to be revolutionary and I wouldn’t hesitate to recommend it to pretty much every boss starting up a new business.

Mistakes can be a good thing

They say you learn from your mistakes, which of course is true, but my life would have been a good deal easier if I had been able to listen to someone else and learn from their mistakes, rather than making them myself.

That is the purpose of this article—to share my mistakes in the hope that you don’t have to repeat them. I’m not in any way guaranteeing that starting your business is going go smoothly and swimmingly as a result of reading this; I hope it does, but in all likelihood, you will make other mistakes that you, in turn, will have to learn from.

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Content Author: Jordan Fried

Jordan is the founder and CEO of Buffered.com—a multimillion dollar software company, and Fried.com—a fast-growing software information website. He has traveled and worked from over 40 countries while building his online businesses. Jordan is passionate about online privacy, blogging, and living a fully remote life.