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How to Evaluate Your Readiness for Starting a Business: A Checklist of Key Considerations





It is not entirely clear what is causing this, but an unprecedented number of people are quitting their jobs, many to start on their own.

If you are one of them, whatever your reasons are, there are things to consider before you make the decision, some of them less obvious than others. In this post I will try to share what I have learned in many years of mentoring startups.


Note: what you are going to read may sound like I don't think this is a good idea. Nothing can be farther from the truth. I think setting up and developing your own business may be the most exciting thing you can do in your professional life and my only aim is to highlight the challenges in order to help you overcome them and avoid common traps.


So here goes:

  1. It looks better on paper - it may be very appealing not to have to work for other people and focus on what you love doing - and it probably will feel good - but in reality so many other things are involved in owning and running a business that you might find yourself one day wondering why you even started. As the business grows you will find yourself dealing more and more with management, finance, sales and marketing etc. and less with what you really love doing and the reason you started on this journey. This is not an inevitability - you can always decide to only develop the business to a level you will feel it has the right balance between your expertise and business management but you need to be aware of this, as growth is the default for every business.

  2. No-one is waiting for you - no need to mention that there is not going to be a paycheck and the end of the week or the month, but if you think sales will just happen, think again. You need to be extremely lucky to start a business based on something so special that clients will bite your fingers off to get what you offer. As talented and special as you are (and I am not being cynical here), if no one knows about you they will not buy from you, so you need to think long and hard about how you are going to reach your target market. Nearly every new business I have ever started working with had little or no marketing budget. Don't make this mistake.

  3. Partnership - having a partner (or partners) has its advantages. You share risks, other people bring their expertise to the business, you can get additional investment, etc., but there are other things to consider. I have seen too many partnerships fall apart because the partners hadn't thought it out in advance. Here are some pointers (you can read more on my blog post about this):

  4. Whom: the fact that someone is your best friend does not mean they are the best partner. In fact, it may be exactly the opposite so thing long and hard if you want to risk your friendship and your newborn business.

  5. Why: different people may have different reasons to start a business. It is extremely important to discuss what are your ultimate goals before going into this so you don't find yourself sometime down the line with diverging goals, pulling in different directions. Make sure your potential partner understands the risks and is happy to take them.

  6. What: figure out in advance what is going to your respective contributions to the business, and what happens if someone is not pulling their weight. Make sure you have a written founders' agreement that includes such eventuality.

  7. Do your homework: you may know everything about baking/editing/building websites/whatever else is your expertise, but this does not necessarily mean you know everything about owning and running a business that does it. There may be a lot under the bonnet that you know very little about so talk to:

  • a solicitor

  • an accountant

  • an insurance broker

  • an industry specialist

An initial consultation is usually free and you can ask them what you need to consider. It doesn't mean you are going to do everything they tell you (they have their own agendas too) but at least you will know the risks and will be able to decide which are the ones you are willing to take.

A piece of advice - don't rely on answers you get on social media. It's OK to look for a specialist on Facebook or LinkedIn but to get all the information you need do book a proper meeting.

  1. Have a contingency plan: no one starts a business thinking it may not work, but with all the planning in the world things may not go exactly to plan. Without some leeway you may find yourself struggling to keep your head above the water long enough to get to shore so have some best-case/worst-case scenarios ready, and make sure you know how to deal with the latter.

  2. Get a mentor: mentors come in various shapes and colours but having someone with experience in running a business (better still, someone with experience as an entrepreneur) at your side, to share their knowledge and support you in difficult times is very helpful. There are plenty of charities offering free mentorships (although some of them come with conditions) but if you can afford it, or find someone who is willing to mentor you for free don’t forgo the opportunity. It doesn’t have to be lonely at the top.

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