Boss Lady

13 things keeping business owners awake at night


What keeps business owners awake at night?  Negotiated contracts, not enough time spent with the family, reliable staff, and cash flow issues are among the reasons that make entrepreneurs toss and turn during their sleep.  This only suggests the difficulty in operating a business in Australia alongside the increasing number of those who are more than willing to try at their own hands.  Yes, most people in business are great at providing the service or product (amazing ‘technicians’) but when it comes to business, some definitely do struggle.  Let’s look into this more.

1. Financial stress

The problem as to how and where to generate income for your business is one of the main concerns that will definitely cause some very sleepless nights.  You may be thinking whether or not your loan will be approved after hours of filling up the application and complying with the necessary requirements.  Have you got enough work coming in so that you know there is enough cash coming in?  Which client is going to go ‘bust’ (bankrupt) and leave you in dire trouble?   Where is the next job coming from?   Is that latest new client going to pay?   I won’t pretend that money does not stress many people.   Even employees worry about money.  Will they have enough money for the kids’ education or for the fridge that broke down unexpectedly?  Don’t forget also the value of insurances – when a crisis occurs, you will be so appreciative of a quality policy.

2. Increasing revenue and profits

Growing revenue serves as the biggest challenge encountered by business enterprises.  How do we get those lead opportunities?   What are we doing wrong when we have a sales meeting, submit a quote and then don’t get the job?  How do we cope with growth if we do get some big projects – do we have the resources, skills and team in order to grow?  Having a marketing plan, well-balanced and variety of strategies and to always be prepared will go a long way to allowing you to catch some zzz’s at night.

3. Recruitment of new employees

Some of my coaching clients find staff one of their biggest challenges, although they recognise staffare also one of their biggest opportunities.  Whilst unemployment is high, it’s still hard at times to find good people.   I also look at some businesses which have amazing staff but are doing things all wrong.   They don’t appear to value their team, not nurture them, train them or guide them.   Think of staff like children.   If you just stick a child in a corner, give him/her food and essentially leave them alone – what will be the result?   Staff are similar; you need to nurture them, help them grow, challenge them, encourage them, show appreciation and make the workplace somewhere they WANT to be.    Do not take for granted quality recruitment of team and well- structured on-boarding.

4. Government regulations

Businesses these days are downright frustrated with government regulations, red tape and government-imposed regulations. However, the reality is that whatever the regulation, all businesses have to abide by it.  If you see change coming, accept it and plan for it – don’t bury your head in the sand.

5. Cash flow problems and management

There are so many strategies to help alleviate this problem.   How frequently and when do you invoice?   What is your debt collection process?  Do you have a business budget?   Do you know your breakeven figure or your margins?  Of course, businesses primarily look for ways in making their business as lean and as profitable as possible but good cashflow is not only about ‘trimming the fat’, it also incorporates increasing sales, getting paid and reduction of waste and inefficiencies.

6. Work-life balance

Many businesses are struggling in their attempt to balance both their life and their work.   I ask people why they are going into business and so often their response is about having flexibility or time with family.   Reality is that often this does not become the case.  It is so important as business owners to implement time management strategies such as delegation in order to use your time wisely.   Discipline is another thing.   I rarely do appointments at night or weekends.  I start super early and work full long days but when it comes to nights and weekends this is my time.  I value it and therefore ensure others do too.

7. Putting pressure on yourself

Ok, I’ll admit I do this myself.  I’m probably what would be called an ‘over achiever’.  I try to cram too much into a day, take on too many projects and drive myself harder than any staff member or client.   If you don’t want to feel pressure then do one thing at a time, take on only one new project at a time, finish things before starting the next and say no (to others and yourself!)    A wish or ideas list is a great place to put these ideas and thoughts to revisit later when/if you have some ‘spare time’ or ready to take the next step.

8. Overwhelming workload volume

As an entrepreneur, wearing different hats is a necessity which may boil down to insomnia.  What I did then was create a detailed list of needs and tasks to keep your business operations smooth.  This is an ever-evolving and never-ending list of tasks because your business continues to grow and you deal with new opportunities with new tasks for you.  I’ve mentioned delegating before and sadly not enough business owners embrace this.   They figure they will do their own bookkeeping, or marketing, office cleaning or filing.   Some tasks are basic, or specialist and can be easily outsourced to staff, casuals or contractors.  Why do things which you are not good at or whichare well below your skill level?   Pass these off and allow yourself to do what you do best and grow your business.

9. Problems associated with people

Managing partners, contractors, and employees can really be challenging and may cause sleepless nights.  You may have employees who are disrespectful to you and your concepts, those who are antagonists to your other employees, or your right hand who suddenly leaves with all the files of your customers.  There are even instances when you fail to make tails or heads on your low corporate revenue and suspect that it is caused by employee theft.  Good coaching, guidance and support will help with many of these challenges.  It won’t eliminate every one of them but will definitely mitigate them.

10. Customer retention

Attracting customers to buy your product or service is not enough to sustain your business.  Aim to turn your first-time customers into repeat customers, most especially when they begin cutting back on their spending and look for anything for the best value of their money.  Be consistent in meeting the changing demands and needs of your customers while ensuring their brand loyalty.

11. Managing administration

Many business owners find this tedious and time consuming – although I cannot stress enough its importance. More and more entrepreneurs use innovation and technology for the optimisation of their administration operations.  When properly used, technology could bring the biggest profit for your business.

12. Turning off the brain

Thinking of things you have to do for your business can cause sleepless nights.  You may suddenly be awakened by ideas or thoughts regarding your business.  It is difficult to close your business mind even when you are sleeping.   I used to have this problem, but not now.   First thing, I never work at night, read business books at night or even think about business at night.  I have also found it incredibly useful to have paper and pen by the bed so you can jot down ideas and not worry all night about remembering something.   Jot and forget until the morning.

13. Planning the next step for business

Often not knowing where you and your business is heading is a worry.   You wonder what is the next step and how do I get there?   Planning not only gives you clarity, it provides a road map and security of knowledge on what will be happening in your business.

With all of the above, a quality business coach can guide and support you.   There are also excellent books on many subjects and specialist help you can engage to resolve a particular problem.   If I can help you in any way, or direct you to a specialist, please just ask – call me on 0411 622 666.

About Donna Stone

Donna Stone is a business coach with three decades of experience. She grew her own business from a garage to be a multi-award winning operation that spanned five locations nationally. Donna works with business owners and other business coaches, consultants and trainers to help them build their own success. Her Coach the Coach ™ program has proved exceedingly popular. Donna is a prolific writer with hundreds of articles written and six books published. Visit

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