Five BIG mindset shifts you need to make as you move from employee to entrepreneur

Transitioning from employee to entrepreneur could be rough. It’s even rougher when this transition happens suddenly like after being laid off, retrenched, or “resorting” to it because of a difficult and dry job market. Moving from working on specific tasks in a conventional job, to being responsible for an entire operation could be hard to wrap your mind around. Having been in this position myself, I realised there were a few mindset adjustments that were necessary for me to exit my cycle of failure and frustration. I had to gain a clearer understanding of what I needed to do to actually grow and thrive as an entrepreneur. Here are 5 major perspectives I gained along the way.


Working in a corporate environment, particularly at management level, often means working on a number of projects simultaneously, that feed into outcomes in different departments. We move away from seeing a process through from the beginning to the end and we lead diverse teams where each member needs something different from us. Soon, we find our focus on specialist skills waning in favour of management and leadership skills. While these are also important for your development, you’d have a much harder time packaging general leadership skills than you would packaging an expertise focusing on solving a particular problem. My advice here is to get back to basics, get back to the skill that opened the door for you. Focus on solving a specific problem or two and learn the intricacies of these issues as deeply as possible. Don’t be intoxicated by a former titles like manager and supervisor, understand that your context no longer ascribes value to that, it’s time to re-tool and retrain.


There’s a phrase that we often use “working in silos”. This is often used to describe members of a team or organisation, who theoretically, are working together towards the same goal but in reality are disconnected from each other in the process. In the corporate environment, we often find that this is the case. While not intentional, you can fall victim to this and carry it with you as you set up your own enterprise. It’s natural to focus on what you’re good at doing, but a business requires you to have a panoramic view of your life, your purpose, your intentions and your desired outcomes. In reality, you’ve suddenly been elevated to CEO and while your expertise may be the core money making activity, you can’t ignore other parts of the operation. Often, I see people delay on business registration, they don’t keep up with paying their taxes, they use excel instead of engaging an accountant, they don’t have proper branding and they leave themselves exposed by not setting up contracts among other things. I’m not saying you should have a full-fledged business with multiple departments from the start, but you need to move from the employee state of mind where you always work in your business to the entrepreneur where you work on your business so it can truly develop.


Becoming my own best sales person was certainly the most enormous lesson I had to learn. I understood that I had to sell in order to earn but in practise, I realise I really did not understand the sales process and I wasn’t selling at all. With the exception of people who actually work in sales, there is this perception that selling is begging. We think sales people are desperate because we might have encountered an over enthusiastic retail sales rep or been annoyed by telemarketers. But in reality, this is not what sales is about. Selling is about relationship, respect and solving problems. Repositioning sales in my mind unlocked a new skill that I didn’t know I had. Now, I actually like sales, because with every call, email or social media post I can close a new customer. In addition to selling, I also had to appreciate the sales process. If I tell you the amount of dollars I spent on Facebook ads, giving away “free” items and then wondering why no one would reach out to buy you’d cringe. I actually laugh at myself now, when I realised that I was stuck in marketing, unsurprisingly, and never actually got to the sales process. I didn’t follow up, I didn’t call anyone and I didn’t reach out and actually ask for the sale. Many books, a couple courses and some coaching later it dawned on me that I was again stuck in my familiar place and not stepping out of my comfort zone to actually sell. As soon as I did, the rest, as they say, is history.


Flexibility when you meet and engage with potential partners and clients is also important as you grow a new business and establish your reputation. A corporate environment is full of policies and rules to keep everyone on track. While these are important, these can make us rigid and can be a turn off for potential clients. Everything doesn’t require a meeting. Embrace the fact that you’re small and nimble and you can make decisions quickly. This is a feature of your business that will be attractive to potential customers.


Working within a particular context can really have an impact on your perspective. I’ll illustrate this with a story. In my years of working in marketing in Trinidad and Tobago, working with real live models almost always meant this person had to be ethnically ambiguous. Whether they were chosen because of some bias or to show there was no bias at all is still a bit of a mystery to me. Recently, I produced my own Mother’s Day lookbook and gift guide as a marketing tool for my fashion brand, A Posh Affair. The book included two models on the cover. However, the models in the image were a mother and son, both of whom were dark skinned and had natural hair. I chose the image because, in my mind, both mom and son looked so happy it perfectly represented Mother’s Day. However, two different people both from different companies thought I was putting my brand at a disadvantage. One comment in particular was that the models were not “relatable”. I soon realised that both these people, as well intentioned as they were, had one thing in common; they had spent so many years inside of a corporate environment where anything that was not considered neutral or mainstream would be rejected. As a result, it became their dominant lense. Remember, the real world is not bound by the mindset of the CEO or management team, so don’t make a company culture your world. Always ask yourself if you’re doing something because it’s the way you’ve always done it, or are you being true to your brand values and the market segment that shares them. Remember, you now have the chance to build your own culture so embrace it.

Yes, making the transition is hard, but it’s not impossible. You need to mind your business, learn and re-learn as much as you can and step out of that corporate identity into your own. The quicker you do this, faster you’d be able to turn a sad situation into one of triumph after a fall. Am I where I want to be? Not quite, but I’m certainly in a much better place than I was before. All the best on your journey! 

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