How tracking a word a day helped me to toughen up as an Entrepreneur & grow my business

I tracked one word a day for a whole year to understand my feelings and emotions about my business and self employment. The video below shows it all smooshed together day by day. In all it’s up and down, polar opposite, gritty glory.

Design by Music:Brazil Samba

The top 5 things this has shown me are:

  1. Flexibility – The importance of tracking and watching things so you can adapt as you go
  2. Consistency -The ups always outweigh the downs and the bads are always followed by a good
  3. Mindset – I should be way kinder to myself
  4. Monitoring – It’s so important to reflect as you go and see the amazing things you ARE achieving along the way
  5. Passion – Business and self employment are fucking hard but it’s given me a sense of purpose I didn’t have before


I’m a bit of a geek. I love to analyse things and break them down until I understand them. Those things include myself and my own mysterious mind.

In December 2016 I came across this graphic by Derek Halpern in an Entrepreneur article. I looked, I laughed, I empathised and I even shuddered a little at the similarities. It definitely resonated. I’d started my own business and was about to hand in my notice at my ‘real’ job. This image made me think if that’s what I could expect a day to be like, what would a year hold?

So each day I chose a word that summed up my emotions around my business. Just my business and just one word. I scored the word and feelings for each day on a range from -10 through to +10 so I could plot it. I had no real intention other than it was something to write in my shiny new 2017 diary.

365 Days

The entire view side by side make for very interesting reading

I stuck with it for a whole 365 days. I didn’t know what I’d do with it or how it would help me but as with anything I set my stubborn mind to, I was determined to complete it and I’d figure out its use after. What I didn’t expect was to learn so much about myself through it and for it to be so fascinating. I certainly didn’t expect it to be a tool for strategic business planning, but now it’s done, that’s EXACTLY what it is.

Tracking my business emotions for a whole year has given me AMAZING insights that I never would have expected from a fun daily diary entry. This year I am doing it again but with the added bonus of having a whole year of data to compare it to, AND the insight to know it’s better to reflect back over it monthly to keep me on track. Because when I really think things are shit I’ll have actual real life EVIDENCE to put me back on the positive upswing.

The Results

On a day by day basis it just looked so erratic.

My year looked like the ECG heart monitor print out of a Tasmanian devil on speed. Over a year it looks CRAZY, but quarterly and monthly it was a way more stable picture. Without the weekly, monthly and quarterly picture to put it into context I think I’d give up now and claim myself as too unstable to cope; without zooming out to see the bigger picture it just looks scary.

The Good

Even weekly it looked all over the place

  • The score I used most was 8 (73 times) closely followed by 7 (53 times). Low scores were used far less frequently.
  • The word I used most was Excited closely followed by Relaxed then Tired, Happy and Organised.
  • The best week was w/c 24.4.17 – we reached an amazing target for sales and I got to meet a truly amazing mentor.
  • The best day was a +10 score and there were 24 of those (double the amount of the worst score). 4 each in 4 different months (Aug, July, May and April) all of which were in clusters. 2 in January then single days in Dec, Sept, June, Feb and Nov. Meaning every month except March and October had AMAZING days in and all the bad months described below all had an amazing day in too.
  • The best month was December.
  • I didn’t use +1 or +2 at all.

The Bad

Monthly view started to look way more how the year had actually felt
  • The negative word I used the most was tired.
  • The worst day was a -10 score and there were 12 of those. 4 each were in 2 different months (April and Sept) – both of those months were particularly hard. Then single days in Feb, March and Nov.
  • My worst week was w/c 4.9.17 I had my son start senior school and an event with Instagram it was ALL way too much to deal with.
  • My worst month was September which also had the worst week in it and it was part of the worst quarter.
  • The school holidays had a huge impact on my stress levels.

The Amazing

Quarterly it started to look way more normal and like you would expect
  • I had 9 bad weeks that came out overall with a negative score but over the year only one bad month! So good outweighed bad 11/12 months.
  • Sales/income didn’t correlate with my happiness the work I was doing did.
  • The average score each day over the whole year was +2.25 so it’s kind of funny that I never recorded scores near this, in fact I actively avoided that score. Yet my year as a whole was a +2.25 and it brought me amazingness.
  • The score I used most was 8 which is pretty amazing especially when you look at the year’s picture it looks so all over the place. So the fact that more days than any were an 8 shows what a great year it really was. This allowed me some perspective and to know in the bad there is still loads of good.

What I Learnt as an Entrepreneur

Design Louise Joines @_doodle_pop_

1. Flexibility

The importance of tracking and watching things so you can adapt as you go

Tracking is great but means nothing if you don’t track in an objective way and learn from it. I’ve seen the importance of getting the bigger picture by looking properly at what I am doing and how I am feeling weekly, monthly and quarterly rather than just flicking through the pages of a diary.

Now I’ll use it to learn and adapt, plus I’m using what I learnt last year to strategically plan my year for 2018. It’s given me info to set targets, know things to avoid, things to do more of, and the people and situations to avoid or seek more of. It’s highlighted the importance of being flexible to adapt to all that flux and change and not be stuck.

I avoided scoring +1 or +2 yet I’ve learnt that stability and stable scores and days are ok. I think to me they seemed too ‘meh’ or ‘blah’, but actually over the whole year the average worked out at 2.25. So actually why was I avoiding this score? It’s probably a really nice stable day in self employment and that I should accept that ‘meh’ and mediocre days are ok in business some of the time.

2. Consistency

The ups always outweigh the downs and the bads are always followed by a good

The peaks and troughs people talk about in business are REAL. It’s not a cliche, for me it was an actual, factual reality. At times it felt like the hardest of months on a micro level while I was in it.

But some of the worst days were bang smack next to the best days. The good outweighs the bad. Day to day things will feel hard but overall it does even out. I won’t panic on a bad day – I now know it’s just a bad day, a better day will come straight or soon, after. It will feel awful at the time but I know now that statistically, and with true evidence, it won’t last. That will help me get through any bad days much faster.

The best month was Dec – it didn’t have any +10 days in but was consistently fab! Consistency is where I want to aim rather than such extremes of highs and lows. I need to try and be more even in my thoughts about self employment to even up the peaks and troughs.

3. Mindset

I should be way kinder to myself

I expected it to be income that impacted me, but it turned out it wasn’t. It was in fact what I was doing and who I was spending my time with that had the most significant impact on my happiness. I thrive when I feel secure so I should see calmness as security not boredom, and appreciate secure work or income.

I’m SO hard on myself and *ram too much in and it’s definitely quantity over quality sometimes. I need to not overbook myself and try to fit too much. Doing just that was the cause of my worst week and worst month. School holidays are especially HARD – I just can’t do it all. I will plan better around those this year to either be off and be with the kids or have childcare in place. Because working at home with them is rubbish for them and for me.

Support networks are key. If you work alone or in an isolated way having others to help you through the good and bad times is so important. I set up Stronger Together a free business support Facebook group back in late 2016. The support from there is like having work colleagues who are friends and this has kept me sane. Having those business besties who get the the ups and downs and can share advice and resources was key to keeping me going.

Tired came up a lot in the words and scores. Not your usual tiredness but an ‘I’m so tired I can’t move’ sort, a total sign of overdoing it (*see ramming too much into a day above). I need to go to bed earlier and not be such a ‘cram it all in the end part of the day’ kind of gal.

4. Monitoring

It’s so important to reflect as you go and see the amazing things you ARE achieving along the way

The importance of stopping each day to pause and think in the moment about how I feel helped so much during 2017. When would you usually be forced to do that? To think “how has today felt” about your business or in fact anything? I can see now that ‘business mindfulness’ leads to being more objective. It’s stopped me panicking and made me more objective and focused about my business.

It’s true that you can’t analyse your business when you’re in the thick of it, you have to step outside to be objective. Tracking daily gives you a small space to just reflect on the day and it’s great, but reviewing the results and implementing changes is what actually moves you forward. Like the charts above show if you are in the day to day you get caught up in the up and down and the chaos. But if you step back even weekly, you start to see the bigger picture until eventually on an annual basis, it all looks much more even.

5. Passion

Business and self employment is fucking hard but it’s given me a sense of purpose I didn’t have before

Far be it that business cliches are not true, being self employed or a business owner is actually truly choc full of all those cliches you read about and for me personally it’s been way tougher mentally than a job. But a job didn’t always give me the sense of personal passion I feel with my business, meaning that I feel finally on the right track. Albeit knackered!

I’m an all or nothing girl, very up and down and I need to work on evening my feelings out and appreciate the in between days. Crashing lows and searing highs are great but I need to appreciate 0 days and 5 days that are calm and normal instead of constantly seeking the thrill of +10 or fearfully avoiding the -10.

Life can feel scary and all consuming when you’re in it on a daily basis with all the ups and downs, but when you look back you see how much you’ve achieved. I felt like it had been an amazing year whilst in it but looking back over it there was so much more I hadn’t acknowledged and tracking gave me all those achievements to relate to as well.

Through doing this I’ve learnt so much more than just about my business, a lot of these results correlate directly with my personality and emotional reaction to life too. It’s helped me be more reflective about ME as well as my business.

If you change nothing, nothing will change

Learning all that means nothing if nothing changes. Thinking differently, reacting differently and actually being different in my business is the key to 2018.

As well as tracking a word a day I had a single word that I chose for 2017. An overall word to guide me. Just one word to keep coming back to and keep me on track of one goal, like a theme tune or a singular mantra to my business life.

That word last year was Brave. It was perfect, it made me push myself and allowed me to go to events and meet people while feeling way out of my depth. To give my notice at work, to try new things, to say when I didn’t think something was right. For 2017 it really was the perfect word.


Having looked at all of 2017’s evidence my word for 2018 is Implement. Not to consume and not create, not to learn but never change, but instead to use what I’ve learnt and help my business grow by doing the following things that I’ve learnt from tracking:

  • Avoid any activities that caused me stress last year, unless their statutory requirements or laws
  • Feel calmer when in a bad period – it WILL get better
  • Have an idea of which months or weeks seasonally for my business are intense or slow and temper my expectations
  • Not panic when things are in a trough. I know factually many peaks will come over a year
  • Be kinder to myself and try and step out weekly, monthly and quarterly to see my progress
  • Recognise the importance of reviewing and having the ability to be reflective and celebrate as I go and the huge benefits of that in terms of how it can keep me focused and motivated
  • Enjoy the journey
  • Keep on tracking. For 2018 I am continuing to track every day but this year I am adding in Kindness tracking too (wouldn’t be Proper Post without it really would it). I’ll be reviewing it monthly and comparing to last year then improving my business and my wellbeing as I go.

This doesn’t just apply to small business owners and you don’t have to be an entrepreneur. It applies to bloggers, creatives, professionals, infact anyone. It doesn’t even have to be about work, tracking your wellbeing is massively valuable on a personal level.

To see the benefits of tracking you can start at ANY time it doesn’t have to be a new year or a new month. You can join me with this tracking challenge and get access to spreadsheets and support and learn how to cope with entrepreneurial life by clicking here.

Originally published at