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Don't Give Up Your Day Job: How To Become A Successful Part-Time Entrepreneur

This article is more than 9 years old.

By day they are accountants, lawyers, technologists, salespeople. At work they're focused, productive, successful, often rising to senior positions within their profession. Yet these unassuming salary men and women harbor a dark secret, a secret that burns within them, consuming their evenings and weekends, pushing their endurance and sometimes their relationships to the limit. Meet the part-time entrepreneur.

For obvious reasons, legitimate part-time entrepreneurs are a rare breed. I happen to know two. Charlotte Pickering is a successful London barrister and mother of two and Naj Alavi is the US Head of Financial Technology company, Xenomorph.

Both are incredibly successful at what they do for a living and both pursue completely different entrepreneurial avenues from their day jobs. Charlotte is the founder and CEO of KiddyUP, an amazing location app that helps parents to find places to Feed, Change, Play and Buy baby and child-related products and services. Naj is the founder and lead designer of a cutting edge men's fashion label in New York City.

I sat down with them both to understand how they manage to pull off two jobs when most of us are still struggling with the one:

Simon:  What are some of the challenges you face trying to balance work life and entrepreneur life?

Alavi: I am very fortunate that the work I do, I can do from almost anywhere and designing clothes does not require me to be in any particular location. But in simple terms, the division of time and labor are two that come to mind.  There are times when I come up with a new design and I am working; I may not be able to give the design the time it deserves and needs to be nurtured into something that could be turned into a pattern.  In such instances, short form notes must suffice, which I can then return to.  There are also times when I am focused on a design and a solution hits me for work; sometimes I will make a few notes, but more often than not, I will stop what I am doing and see things through so that I remain on top of work too and then return to my design.

Pickering: Every day is a huge challenge. I have two pre-school children, I work as a barrister and am co-founder of two companies - one of which, KiddyUP, has a presence in both the UK and Middle East and has just closed its first round of funding. The challenge is trying not to allow one of those things to impact negatively on another.

The nature of my "day job" is such that it requires absolute full attention - it's a profession and it is far from easy. Having moved from London to Cornwall a few years ago my practice is quieter and that suits me well. For the moment my "entrepreneur life" fits neatly around it. I am lucky to have my husband and my parents who are able to step in with childcare. I work from home in any event so my children know I am "there" if they need me, albeit sometimes mummy has to lock the door!

Simon: Something's got to give, what is it? Is it free time, family time, sleep, eating, what?

Alavi: It has varied; I have given up a combination of free time, family time, sleeping and eating as well as other pursuits such as painting.  However, the repercussions of my actions were to put a tremendous strain on my relationship with my wife, a lack of sleep started to have an adverse effect on my ability to work cohesively and not eating properly drained energy.  What I learnt is that for anything to be a success, you need to find a working balance and try to keep within its parameters.  If you are unable to spend time with your partner, ensure that you make up for it and don't take them for granted.  If you skip meals, catch up; if you miss a few hours of sleep, try to make up for it by relaxing.  It might sound obvious, but without the right balance, you will be off-balance and something will give and perhaps break.

Pickering: I stay up very late as I very often only start working once my children have gone to bed. Free time? What's that?!! I enjoy long drives to distant courts, let's put it that way. I do joke about being a "supermum" but it is far from the truth - I would be lying if I said I held it together all the time. I do a good job of presenting a calm and organised façade but behind the scenes it's a tempest of nappies, court papers, prototypes, and App download analytics! Yeah and my eating schedule SUCKS.

Simon: Presumably you need a tremendous amount of discipline, can you tell me about this? What techniques do you employ?

Alavi: Absolutely - without discipline nothing ever gets done.  I will not shy away from saying that I have wasted a number of years not following through and simply poking and prodding the odd design here and there.  Friends and family pushed but I realize now that what was missing was discipline and perhaps not believing in myself.

Now I have a different outlook - I remain focused; I set myself goals and break things down into small tasks of larger projects and actively work to tick off my to-do-list.  I engage with myself and ask questions of myself to take things to the next level.  A few years ago, I really thought my designs were simply the best; looking back now, I realize some were downright awful and I had fallen into a pattern of designing for the sake of designing without giving much thought to the end result.  There was a distinct lack of discipline as I was not setting myself objectives or goals.  Recipe for failure 101 - don't be disciplined.

Pickering: I employ the "answer emails with one hand whilst spoon-feeding the baby with the other" technique. Seriously though, it is amazing how much you can cram in to short intense bursts of work if you know that is the only time you will get that day. I've done office jobs and what with making a few cups of tea, chatting to a colleague, taking a slow walk to the loo, I probably got as much done during a whole day as I can get done during my daughter's two hour afternoon nap now. Add another five hours after they're in bed and you've got a whole working day there.

Simon: Is motivation ever an issue? Do you ever get the urge to quit your job or stop pursuing entrepreneurial life? How do you stay motivated?

Alavi: No, I am always motivated on whatever task I am doing - even buying groceries!  Keeping a keen eye on the end goal is what keeps me motivated.

Pickering: Yes, motivation is an issue and of course there are days when I feel like I want to quit the whole damn lot. However, I am very lucky to have such a brilliant business partner - Zoe Bermant - who keeps me going through the tough times! She recently sent me a gift voucher for a full body massage at a salon down the road from me - seriously could you get a better business partner?! We remind each other to think about the end goal, why we are doing this and where we see the KiddyUP platform in 3-4 years' time. We have such immense plans for it and can see such huge potential there is no way we will give up without giving it our best shot. Others believe in us too and we have some super exciting collaborations coming up - it gives us a real boost when big players "get" what we are doing.

Simon: How supportive have your families been? is family important or is it a personal mission?

Alavi: Without the support of my family, I don't think my designs would have come along as far as they have.  My wife is my first sounding board - if she doesn't like something, more often than not, the design or idea needs a rework.  She saves me countless hours and days.  My father and brothers are willing participants to try out my designs and give honest feedback - which, at times, can be difficult to hear but is needed for fine tuning.  Without family, it would be difficult.  My recent marriage was the kick start I needed.

Pickering: Very supportive indeed. I come from a family of business owners so they "get it". Ultimately though it is a personal mission (or rather the mission of me and my fellow Co-Founders) - as a "tech startup" we have a very different business model to the traditional small business most of us in the UK know and understand. Due to this there is much that my own family can't help with, but to be honest it is the practical help that is worth its weight in gold.

Simon: Do you plan to quit doing your day job at some point? What will be the tipping point for you to fully commit?

Alavi: Being part of what we are doing at Xenomorph and achieving at my day job provides the drive for what I do with clothes.  What I do at work is very analytical and practical - so being able to balance that with the creativity of designing custom suits is a beautiful balance to bring a sense of yin and yang to my outlook. As for a tipping point, I have not really given much thought to that as, right now, I am able to combine my passion for my day job with my love for clothing design.

Pickering: At the moment I am taking each day as it comes. With a young family I have financial commitments that I simply have to meet. Life isn't so simple as saying "when I can earn x amount from my company I will quit my day job", especially when the financial security and well being of your children is on the line. As with everything I truly believe the answer will slowly but surely become blindingly evident.

Simon: What advice would you give other aspiring entrepreneurs who perhaps have an idea or a passion which for whatever reason can't commit themselves to it 100%

Alavi: If you don't breathe life into your idea - no one will.  Never let yourself be in the position of looking back and thinking to yourself, I wish I had given it a go - do it and if you can't give it 100%, give it 90%, if you can't give it 90%, give it 50%, if you can't give it 50%, give it 10%, if you can't give it 10%, give it 1%.  Don't let your passion die. Try to assign some time in your daily or weekly schedule; block out time where you can focus on what it is that interests you beyond your day job.  Believe me, you will not regret it.

Pickering: If you have a great idea there is no reason why you can't start giving it some time during the evenings or at weekends. If you are truly committed to it, you will find a way! We all know that most people cannot afford to simply drop their day jobs - life simply isn't that straightforward. Get yourself a mentor - someone that can guide you through laying the foundations in preparation for taking that plunge. I've had some fantastic coaching through Oxford Innovation (www.oxin.co.uk) via their Grow Cornwall program (www.growcornwall.co.uk). And as Richard Branson has said - prepare your parachute! Think about the consequences if your business fails, and do what you can to minimize that possibility for example by securing financial help or taking on partners.

Alavi: Life is too short to not give your passions wings and your inner child a reason to smile!