Finding The Confidence To Start Your Own Side Hustle


By Chelsea Cox, founder of Well Defined and Well Assisted

There is no easy way to say this, there is no magic “start your own business” potion or book that is going to give you immediate business confidence, it’s something that develops over time. What you do need however is complete conviction, passion and belief in your business/brand/product, the confidence in your offerings will come from every baby step you take from business conception, from officially setting up yourself as a legitimate business to creating a website, every step will give you more confidence in yourself, your abilities and your business. Yes there will be setbacks, moments of doubt and the odd piece of negative feedback but as your confidence grows you will learn to not fear them but to embrace & learn from them, it is what builds you as a business person. It’s those moments that will teach you to pick yourself up, dust yourself off and start again in the morning. If any business person was to be honest, they would tell you that they ALL get moments of doubt, not always necessarily  in themselves but perhaps in a business decision, partnership, new product...etc  what drives them forward is the love and belief in what they are creating and that is exactly what you need to do, focus on the long term. 

One piece of advice I stand by as a business mentor is to separate the brand from yourself personally as much as possible, I work with a vast array of clients from brands to freelancers, influencers to coaches and something I quickly establish in my work with them is a level of separation, even if you are a freelancer this is completely doable. The ability to be able to step back from your business and know that you are ok, any feedback or setbacks are not impacting your own personal health, family and life really helps. That separation will give you perspective. 

On the subject of perspective, a question I have asked myself when I am going through a moment of uncertainty or if I have to make an impactful business decision is, what is the worst that can happen?

I confront the worst case scenario happening in my head, talk myself through it and come up with a solution. As an example, when I started my business my confidence panics came from the thought of potentially losing my house if I couldn’t make the same level of salary I had been making in my corporate career, immediately I solved that problem in my head with the reassurance of, I would take any PAYE job to replace the income I needed whilst continuing my business on the side until it was “safe” again, I was never going to give up but giving myself a solution to my worst case scenario gave me the confidence to continue and confront my moment of uncertainty straight up. I know a lot of people advise to push these thoughts away but I am a big believer in confronting your fears head on and moving on. 

Speak, this is something I cannot recommend enough, speak to people in the same industry as you, speak to people who are freelancing, speak to brand owners, speak to people at events, speak to people at your co-working space or the coffee shop you work from, the more you talk about owning your business, the more advice you receive, the larger your network, the better your contacts, the more trusted fellow business women/men you meet this will always equate to more confidence. That feeling of not being alone and of being supported is solid gold!

Know your worth, this is something I do a lot of work on with my clients. Generally speaking the majority of my clients will tell me that they feel they have to discount or do things for free in order to prove the worth of their services or products when starting out. This is absolutely not the case, you have to set your worth and stick to it. This will help you develop the confidence to walk away from a sale or client if your worth isn’t being appreciated or valued. 

Set out your brand values early on, work out who your ideal client is, the messages you want to align with, you ideal project, the impact you want your business to have on someone and don’t be afraid to turn down work that isn’t serving your brand values, have confidence and conviction in your brand values. I have been approached by many a brand that hasn’t aligned with my brand value and ethos so I have decided not to work with them, in the long run this will only benefit your business and create a stronger trust in your brand. 

Learn to celebrate yourself, be proud of every single achievement and don’t ever lose that from celebrating your 1st client to celebrating your 50th client, every step matters. Be proud of the journey.

Remember to keep perspective, know your worth, stick with your brand values and know you are not alone. 

If you are in need of business support whether you are just starting out or established & uncertain of your next steps, I can help, I offer one off or ongoing support so please do get in touch. 



Chelsea Cox, founder of Well Defined & Well Assisted. Having spent over a decade in commercial management for companies such as L'oreal, The Telegraph and Hearst UK, Chelsea launched Well Defined to support women in business & female led brands in their strategies, PR, business planning and expansions.

Chelsea offers We Are Auburn readers an exclusive initial 1 hour business consultation & review for £150, get in touch quoting "WeAreAuburn" through email: