SG085 - The harsh lessons from a year in business

A year ago, on the 30th April 2018, I left the safety net of my corporate career, I left a business I had worked in for over ten and half years, to do something I never thought I’d be doing, starting my own business. 

I’d been one of the lucky ones as far as my corporate career was concerned, as a qualified accountant I’d never once been out of a job, I moved up the senior ranks in the finance function and was lucky enough to work internationally with global brands I really admired.  I also enjoyed the trappings of a great salary and a healthy bonus scheme working for a business that I thought I’d be part of for many more years.

But, I had an inner niggle, something was missing for me and I was getting frustrated with the inner knowing that I needed to look beyond the veil of safety I was clinging too. 

I had begun to notice the patterns - people following the same routine every day, the expressionless faces on the morning commute, people filing off trains onto the escalators a bit like lemmings I thought, following a herd, moving on autopilot towards, what looked like from their faces, impending doom.

It caused me to question the life I was living and whether I was really doing what my heart desired.  I wanted a spring in my step, I wanted adventure, variety, to be stretched and to be around people that were passionate about doing what they were doing every day.  I’m absolutely sure there are much easier ways to achieve the above than starting my own business but something inside pushed me to leap and go on this adventure!

It’s been a huge year of learnings for me so now I’m at the one-year milestone I thought it would be helpful to share my lessons, of which there have been many! 

Some of these I wish I had known before I made the leap, although perhaps I would have hesitated to leap if I did!  So I hope this will help you if you are considering embarking on the same journey.  Even if you aren’t it might help you to understand a perspective from the other side so you can appreciate what you have!


1. Be ready for the many hats you will wear 

Call me naïve or stupid but when I left my corporate career I’d never really considered all the different hats I’d be soon be wearing.  I had left to do executive coaching and leadership development and the only thing I had on my mind was the excitement of helping people overcome their obstacles and making a difference in their world. 

I had some idea when I left my corporate world that along with being a coach I would be my own admin, finance and strategy person.  I know this will sound really silly and although I’d like to consider myself reasonably intelligent I actually had no real grasp of the fact that the single biggest role I was actually leaving corporate to do was a sales role. 

Now, if I’d really considered this at the time, I’d have run for the bloody hills! A sales person, me, no way! That’s not what I was signing up for, I was a finance executive I didn’t have a clue about actually making sales, I was the person who just added them up!   

I learned the hard way and I have to confess I’m still learning because I’m certainly no master at selling just yet, but the truth is, if you don’t figure out how to do sales you don’t have a business, period.

I have a much greater level of empathy for anyone doing sales and marketing than I ever did being in corporate.  Trust me, anyone practicing those disciplines deserves a huge applaud because not only is it an incredibly challenging skill to master but the mental toughness needed to be comfortable with rejection is something I never appreciated! 

So whether you are a finance person looking to business partner better or someone considering making the leap into entrepreneurship I’d encourage to really develop your skills in this area – I reckon if you can master selling you can achieve anything!


2. Understand you need boundaries and routines 

Going from a regular routine and a clearly defined role into a new environment of total uncertainty was pretty scary.  At first I felt the freedom of not having the dreaded commute but then after a short while I felt a little bit lost and clueless. 

My day job had so much structure that I struggled with the lack of it in my new world.  I’d taken a leap but I hadn’t really considered what the day to day would look like or involve. 

I was bad employee in the first couple of weeks as I indulged in my new-found freedom and then I became the bad boss the one that became the task master that didn’t know when or how to switch off – I’d wake up and jump on to my laptop as soon as could and then struggled to switch off.   

What I learned was that you have to set boundaries so you know what to expect of yourself.  Also that it’s absolutely imperative to define your own structure for the day and have a clear morning routine so that you start the day well and set yourself up for success.  It’s really easy to wander around like a clueless zombie and find yourself in your head first thing in the morning (yes this was me) so having the discipline of having a nourishing morning routine really takes some of the stress out of the day whether it be exercise, meditation or journaling or some combination of all of the above.

Another thing I didn’t really understand in the beginning was the importance and the value of my time.  I was doing a significant amount of networking and I failed miserably to plan my day.  I found myself in and out of the city with sporadic appointments each day and lost a lot of time in commuting from one to the other.  Sometimes it’s unavoidable but it’s so important to recognise where there is opportunity to bunch meetings together on a specific day a week dedicated for networking and have a base location for meetings where possible so that you don’t lose more time than is necessary.  


3. Be ok with it being messy 

In corporate I had the luxury of great systems and processes and more often than not you’d be working on solutions to problems in anticipation of them arising and you’d have time to perfect things before you actually had to deliver.

One the biggest lessons I learned is that if you work that way in the early months of your business you don’t achieve anything also it’s an easy excuse to avoid doing the scary work of getting in front of people pitching. 

I could lose hours perfecting a brochure or creating a perfect programme but unless I was actually getting out there delivering work it was a complete waste of time. I learned I had to get comfortable with good enough and just get out there and deliver and test if it was what people wanted.

I learned you actually have to work the opposite way to the luxury of most corporate environments, you sell the concept and framework first and then you develop it.  As a dear friend guided me you must ‘create the problem first then solve it’.  In corporate I’d spent my whole career solving many problems that hadn’t even occurred! 

This was so alien to me!


4. Have your tribe 

I didn’t consider who I had on Team Glin when I set out on my own and truthfully I found the early months incredibly isolating.  When you move from having a bustling office and team around you it’s a huge transition.  I missed having people around me and I was working from home a lot in the early months. In the absence of a formal team I learned I needed to create a team of my own, a team that would help buoy my spirits and keep me honest on this new path.  I live across the other side of the world from my family but I leaned on them very heavily and still do.   Without their unconditional love and support I don’t think I’d have made it through the last year. 

I also learned that I needed to have the right friends to share the journey with, most of my friends were in corporate so couldn’t empathise with me when I was having my moments of fear and self-doubt.  It was hard because most of them would just say “you can always go back and get a job in finance” which is true, but it’s not really what you want to hear every time you hit a road bump.  You want a pit crew that are going to stand for you when you get scared, a team that will have your back but also challenge you to do better.  You want objectivity but also need those that are interested in seeing you succeed not ones that are just waiting for you to fail.

I wish someone would have told me to really cultivate Team Glin prior to making the leap because without this team in place, the journey is so much harder.


5. Be aware of your mental, emotional and physical health 

This is the biggest and toughest lesson. I had no idea embarking on this new adventure could have serious consequences for my health and wellbeing – incredibly naïve I know.  Given one of the foundation levels in Maslow’s hierarchy of needs is security, I didn’t really make the connection that removing the security of a regular monthly income could have significant adverse effects on my mindset.

Being a finance executive I’d done the math and left my career with a financial runway that I would leverage as I developed my business.  But even with the maths done and with no immediate risk to my safety my mind took me to a whole new level of fear.  Honestly it was like nothing I’d ever experienced.  I’ve had an income from the age of 15 when I first started working weekends whilst at school, so this was the first time since I started working life that I didn’t have a regular monthly income. 

My brain took me to deep dark places, and over the last 12mths I’ve experienced both high anxiety and depression and if I’m to be brutally honest there were moments where I wanted things to be over.  I don’t believe I would have ever have harmed myself but it really scared me that I could actually understand why people committed suicide for the first time in my life.  I soon learned that entrepreneurs are highly susceptible to mental illness (50% more likely) due to the high levels of uncertainty and pressure they are navigating. 

Nothing had prepared me for suffering a mental illness with starting a new business and again had it not been for the loving support of my family and some dear friends things could be looking very different for me. 

Again, it’s logical to think I could just easily get another job so why did my mind take me to that level of suffering but the truth is when you’ve been brave enough to make the leap in the first place the last thing you want to have to do is give up and go back to the day job. 

Shame also plays a huge factor, my mind was under so much pressure to succeed that it kept playing on loop the fear I had of failing, and so the anxiety and depression at times was debilitating.

I described it as losing the ability to adult.  I remember walking into a supermarket once and not even knowing what I should purchase to create a meal – I was so overwhelmed I walked out with nothing, I lost weight because I wasn’t eating properly.  I exercised lots but had little energy without the right food for fuel and mentally I was a mess. I lost the ability to make decisions even simple ones like - should I go to the gym or go for a walk, I had many moments of circling my hallway as I struggled to choose. I woke up experiencing fear and dread and at times barely wanted to get out of bed to face the day because I felt like I was stupid and was foolish to think I could develop my own business.

Thankfully I’m out of the deep end of my mental illness, although I’m very aware that I could easily be there again so self care and support is incredibly important. As I mentioned I didn’t have Team Glin in place to support me and many of my friends didn’t understand what I was going through and some even distanced themselves because I wasn’t the same Glin anymore, so I felt incredibly alone.

I’ve since set up a Start-ups Unmasked community group which focusses on creating a safe space for entrepreneurs to share their journey with those on the same path.  I learned that many people experience the same rollercoaster I did but not many people speak of it, and many suffer in silence.  There is always pressure to keep the shop window of your business well presented so it can certainly be hard to find a group of people that could actually hold space for you be open about the challenges of entrepreneurial life in a safe and confidential way that doesn’t adversely impact your business. 

If you are reading this and are an entrepreneur struggling, please get in touch, and I’ll share more with you about the community. Please note, this doesn’t replace getting professional help if you are in need but it is a safe space to share your journey with others who understand.


6. Be ready to pivot

Other things I learned along the way were being able to adapt my offering and develop products to deliver a solution to the problem the customer had rather than just sell what I had to offer.

When I set out to start my business I knew from the outset that one-to-one coaching was not going to be scalable so I focussed on developing in areas I could scale as well as recognising that the coaching would bring in a regular cashflow whilst I developed corporate work that had much longer lead cycles.

As an entrepreneur that is looking to generate income you really have to get savvy about solving the problems the clients have and creating solutions that meet their needs.  In the early days you don’t really have the luxury of saying ‘hey this is my product take it or leave it’ as you are trying to build a business so it’s important to be flexible and acknowledge how you will pivot if necessary.

I do one-to-one coaching, leadership development programmes, different workshops half day/ full day along with financial mentoring and business coaching.  I’ve developed bespoke programmes for clients and this has taken time but without recognising I needed to be adaptable and be able to pivot on what I could offer, as well leaning into my full skill set and leveraging my experience I was never going to be able to succeed.

I still have aspirations on where I want to take the business and the impact I seek to make, I know it’s going to take time to reach that destination so in the meantime I’ll continue to adapt and pivot appropriately.


7. Have a clear financial run way 

You need a financial safety net and be prepared to consider exactly what you would be willing to sacrifice to achieve your goals.  I walked away from really healthy package and I don’t have a partner to carry me financially as I embarked on this journey so I really needed to have a good run way of cash to leverage.

I got really strict with myself cutting back on all expenditure that I deemed to be a luxury.  I don’t have Netflix, I don’t buy new clothes or shoes unless I have to replace something, I don’t buy expensive brands of products and don’t have 15 different bottles of perfume!  I realised that for the short term I needed to live a different way because I couldn’t indulge in the same way I once did having lots of disposable income.

It’s important to give yourself a budget for self care because if you are the business you need to keep yourself well but you have to be clear up front what that looks like and choose things that will help you navigate forward not just numb your pain when things are challenging.

Also don’t go crazy like I did because I did end up being really harsh and extreme (when the high anxiety and my mental health was at it’s lowest) when I decided spending money on a new mop was a luxury and that I’d be able wash the floors by hand with a cloth!

Thankfully I now have a mop and I’m acknowledging that whilst I have to be sensible, I don’t have to be ridiculous.  But it is worth recognising that financial security is going to be your number one pain point so really give yourself the best chance of success.

I went all in with my business and left my job to build something from scratch but if I had the time again I’d have definitely started a ‘side hustle’ before quitting my job mainly due to the challenges I faced with my mental health in the early months.  I would have felt much more secure had I established the business before leaping.  I certainly accelerated the learning curve doing it the way I did and truthfully for me I know it suited my personality mainly because I’m an all in kind of person, but it certainly wasn’t easy and the health impact was a huge price to pay.

I would encourage you start your business when you don’t have the financial pressure to pay the bills with it.  Also a two-year run way would also be advisable if you can get to that level of savings.  It takes much longer than you think to get to a consistent cashflow level and you don’t want to stop being able to live and do fun things whilst you build it up.


8. Factor time for play

I mentioned setting boundaries earlier but it’s worth mentioning that play is really important to keep energy levels up and to sustain you on this path.  I did not do this at all in the early months and I’m still learning how to do this effectively, because when you are accountable for everything there is a lot of pressure to perform.  But you need the play time to connect you to why you are doing this this in the first place and it helps to switch off and rest your mind especially when it never stops racing. 

Creativity also comes from play and I have some of the best ideas come to me when I’ve actually given myself permission to play without feeling guilty.  I am learning to see play as fuel for my soul and also to remind myself that I have to feel alive whilst on this journey because it’s a long road.  Play helps to reset me when I feel overwhelmed and it reminds me that life doesn’t have to be serious all the time in fact it’s actually significantly better when it’s not!  I certainly perform better in my business when I give myself time to play and it brings more warmth and energy to everything I do.


9. Build partnerships

I also learned really early on that my energy comes from being around people so building partnerships with people that shared the same values was one way I could still have the flexibility of building my own business whilst still being part of a high performing team.  When you work for one company you don’t really get to choose all the people you work with and not everyone lives the same values even if the company itself has defined them.

The gig economy that I am now a part of is really disrupting the way we work.  I feel really privileged to be a part of it and experience first-hand what it truly means to business partner.

I’ve been lucky enough to find businesses that share the same values I have – they too are performance focussed and heart led.  I love being around people that are incredibly passionate about what they do, raise the bar consistently when it comes to performance and they continue to look for new ways to innovate to get better results.

Being part of The Outperformer team and also the Transition Hub gives me the opportunity to bring all of my tool kit to the table – I get to leverage my finance acumen in a new way, deliver workshops, coach and mentor.  I get to be around people I love working with, those that are driven by the same goal – to make a genuine and sustainable impact for the people we serve.

Partnerships extend to clients too, finding those initial clients that are willing to give you a go when you first start out is so critical.  I want to be in this for the long haul and I’m well aware most businesses fail in the first three years of starting up, so choosing to build relationships with clients that I can have a long-term relationship with is necessary. 

Also if you know anything about cost to serve you’ll know that it’s much harder to acquire new customers than it is to nurture the ones you have.  Give value and then give more value and then more.  It’s not a short game so if you are expecting an immediate return with this perhaps this wouldn’t be your approach but I’ve learned that I only get more comfortable with selling when I can look myself in the mirror and know that I’m really giving value in a way that is meaningful and impactful to others.  So that’s how I work – it aligns to who I am and it’s the kind of person I want to continue to be in the future.


10. Do your homework

With my background in finance and driving performance in large corporates I had a false sense of security around thinking I knew exactly what it took to run a business, but the reality was I’d never set up a business from scratch.  I’d never worked for a brand that was a start-up, unestablished and unknown and I certainly hadn’t worked for a business that didn’t have significant resources to invest in getting experts in sales and marketing and business development!

So in reality I had no clue what it really took to build a brand and a business.  There was so much I needed to learn about the basics.  If I would have my time again I’d do better homework, I’d have done more to learn about what it takes to set up a small business and learning all the stuff that I didn’t know I didn’t know – there are so many courses one can take and get some insight into what is needed.  I honestly can’t believe that as an intelligent corporate executive I didn’t even consider doing any of this before I jumped.  Of course I figured it out, yes but it could have been a lot less messy and I would have got a lot further if I had!


11. Get a coach and mentor

I’ve had two coaches and several mentors over this last year and I couldn’t have got by without their support.  I needed people that would help me see what I couldn’t see, those that were ahead of me on the path to help guide me.  There is so much unknown and the emotional rollercoaster is immense so having professional support to keep you on track and also to hold you accountable is critical.  I can’t tell you how necessary this is, I’d have made a gazillion more mistakes than I already did if I didn’t have this support network.

Choosing the right people is critical as some focus on supporting your mindset, others focus on the practical skills and tools you need to implement and in reality you need both. When you haven’t got a clue how to do something you need someone that can ask the right questions yes, but sometimes you need people that are just going to tell you what to do.


12. You absolutely must lead with H.E.A.R.T. 

Finally, I learned that I’m actually living and breathing my own change leadership framework and actually I have no choice but to.  I have a strong belief that change leadership begins with self-leadership and that we genuinely all have the power to make change happen, but we often need to learn it for ourselves!

So when it comes to H.E.A.R.T.  

I have HOPE – a belief in a better future than today and a genuine belief that I can make it so I focus on how I can find the right steps to make it a reality.  I have ENERGY – the fuel to go after my goal, a continued focus on looking after my health and leveraging the resources I have in terms of support network.  I’m taking ACTION – and most importantly with this, it’s authentic action, doing the work that aligns with my values and that which unlocks potential in others.  I have RESILIENCE – I continue to get up after each set back but more importantly I have a deeper resolve than I have ever had to continue on this journey - nothing worth having comes easy.  Lastly, I have TRUST – both in myself and the path as it unfolds, a deep faith in the vision I have for the future and the one I want to be a part of creating and I’ve no doubt that if I continue on this path and stay true to myself and the people I’m serving that me having a performance focus whilst leading with my heart will serve me well.

If you’ve read this far, thank you. It’s not always easy to share what goes on behind the shop-front window but if I want to be part of creating a world without masks then it’s absolutely necessary.

If you are interested in learning more about the work I do and see if I could help you and your business I’d love for you to get in touch -