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Alan W's story on... entrepreneurial moonlighting

Alan teaches us about the value in taking the part-time freelance route to ignite our entrepreneurial journey. Who says we should choose between being a full time employee and being a full time entrepreneur? There are many lessons to be learnt along the way and doing entrepreneurship in tandem with building one’s career, we can feed both streams.

I have learnt a lot about soft skills like dealing with clients, invoicing and quoting, and so on, which continues to give me an edge as I accelerate my career.”

Alan has an impressive solid stream of moonlighting business as a visual designer. He speaks of no hesitation when initially embarking on his moonlighting endeavor as it held much less risk compared to those who may make the full time jump to entrepreneurship. When taking this route, ‘it is very easy to say no’, and with that comes the freedom of choice in terms of how much you want to take on. You remain in control when you exercise entrepreneurship as a secondary income stream over it being your livelihood.


“My freelance career really started off the back of already having worked for a company and when I later moved on, they continued to hire me for work. I still work with them ten years later!” This pattern has followed Alan in his entrepreneurial journey where interestingly former employers have continued to find ways to keep working with him. He shows us the power of how great work today will continue to pay off tomorrow. His clients enter a low risk engagement working with Alan as his consistency in quality delivery and his professional demeanor never fails. If we view and treat each and every good client we come into contact with, with nothing less than our best, they become clients for life - priceless.

"I am very fortunate to have gotten myself to a place where I can choose who I want to work with. It is an additional income and creative opportunity to do something I enjoy, and I am not in a position where work is forced on me.”

Alan holds a longstanding relationship with his clients, many years in the making. “We know each other well, they know the level of work I deliver, and managing expectations has become easy for both parties”. This also feeds into his referral funnel with more unexpected business opportunities. Alan has set himself up to constantly receive a varied array of work engagements that keep him interested, inspired and challenged, all offering opportunity to continue to learn and grow while flexing his entrepreneurial muscles outside of his nine-to-five.


Alan balances all that he has on the go with poise and ease, what IS his secret? Discipline. “On any given day I am clear on what I need to get done. When it comes to my work I take an analytical approach.” In addition, Alan makes smart and calculated decisions in terms of who he decides to work with as the wrong clients in a moonlighting capacity, work can quickly get out of hand.

“In the past I have had clients whose relationship I ended because it wasn't working for me. In this case, YOU are the most important person, not necessarily meeting all their needs no matter the cost or burden it places on you.”

We are reminded how important decision making such as this is for those who moonlight so that their career goals are not impacted by negative moonlighting experiences - it should not come at too much of a sacrifice to oneself.


“With anything in life, exploring entrepreneurship in the form of moonlighting can get rough, there are ups and downs. Just stick through it and make sure you are still focussed on doing what you want to do.” For some moonlighting becomes a full time gig, for others like Alan, it can stay in its lane while you grow in your career, using it to learn, supplement income, and challenge one's own craft.


Patience and perseverance is essential for those who moonlight due to the fact that this is being done during personal time. Alan advises us to work on finding ways to deal with this natural flow of frustration that comes with the nature of moonlighting.

“It takes time to build habits and habits are a very powerful thing. Once they are formed you can learn to use them to accomplish a lot.”

Alan's vision remains strong and clear: to learn as much as he can from what he gets exposed to, forming long-term relationships, and to take all he can for each opportunity both from a soft and hard skills perspective. He applies all lessons to both his personal and professional life. His advice to those who want to embark on the moonlighting endeavor:

“Be very sure this is what you want to do. Start slowly. Finding good clients takes time. Know yourself, your values, and align these with how you approach it. Give attention to time management, and building efficiencies to make this type of work works for you.”

We thank Alan for reminding us that entrepreneurship is all around us, it comes in many forms, and moonlighting holds a firm place.



“Solving niche challenges Founders face”.


Illustrator: Lisa Williams (Instagram: @artist_llw)


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