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Survival Tips for Entrepreneurs During a Time of Grief

Survival Tips for Entrepreneurs during difficult times
February 25, 2022

Today I want to discuss the difficult subject of grief with you and share some tips on how to stay the course with your business and career when your personal life is imploding. It can be a difficult and lonely journey trying to keep things afloat and moving forward when submerged in grief. These survival tips will help you during times of upheaval.

A good percentage of my clients are individuals who have or are going through, profound loss. They reach out to me because piles have built up everywhere, documents are being lost, their “to-do” lists have become titanic, and they are no longer able to keep the tide of chaos and overwhelm they feel at bay.  Their grief can stem from the loss of a loved one, the failure of a relationship, a catastrophic health diagnosis, or the failure of a business. Their personal lives, health, and income are all being impacted. I can tell how long an individual has left it before seeking help by the type and quantity of chaos that has accumulated. It could be months, a couple of years, or a decade. It’s usually a decade though. A decade of things building up, dreams being put on the back burner, and health issues being ignored.

A client of mine put it this way:

“Grief is like this backpack you are carrying, that you will carry your whole life. It’s always there. Some days it feels like you are carrying a backpack of bricks and other days it’s just lip balm”.

The insights and tips offered here are to help prevent you from tipping over when your backpack of grief is heavy. Why? Because one day you will emerge from the fog of grief and loss, and when that happens (which it will) you don’t want all those bricks to have turned into mounds of clutter, repairs, unpaid bills, and missed opportunities.


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Short-term memory is affected during the grieving process and cognitive responses slow. You may feel you are in a fog and struggle to recall basic information like a colleague’s name. “There can be a disruption in hormones that results in specific symptoms, such as disturbed sleep, loss of appetite, fatigue, and anxiety”, says Jannell Phillips, Ph.D., a neuropsychologist at Henry Ford Health System. When all these symptoms converge, they take a toll on your mind and body, with the deterioration of your short-term memory being a significant by-product and cause of anxiety. But as disorienting as these experiences may be, such forgetfulness in grief is normal. Your memory will slowly come back, you may need a little nudge here and there, but it won’t be long-lived or permanent.

Here are some tips to help you with any short-term cognitive and memory issues.


Daytimer/Calendar: It is important to keep track of what you have done – not just what is scheduled. This can include such mundane things as “Spoke with Jane about walking the dog”, “Watered the plants”. Losing track of time becomes an issue on many levels.


Daytimer -Day a Page

It may take a few years before you get back to your normal mental capacity. I would suggest you purchase a physical day timer, with a day a page. Every evening jot down who you saw, things you did, bills you paid, and notes. This daytimer can be used for personal and business notes but it not your official calendar, it is a support tool. It is important to write things down. Your brain is overwhelmed – doing this simple task at the end of every day will help reduce anxiety and help support challenges you might be experiencing with short-term memory.


Digital Calendar: This is the calendar you use to make sure you show up on time and on the correct day, for appointments. It needs to be digital and work across all your digital platforms (laptop, mac, pc, mobile phone, email). It should have the ability to set reminders, alarms, colour code, have a good search tool, sync with email, and not expire old appointments. When putting in an appointment, add the phone number and/or address… don’t rely on memory for this. Just get into the habit of adding as much information as possible.


At the start of every day look at your calendar, making sure you are looking at the correct day. Once you are sure of day and date, then look over your schedule so that you get a spatial awareness of what’s ahead for you that day.


Set Alarms and reminders: Losing track of time, even what day it is, is a constant challenge. Set a reminder in your calendar but don’t forget other sources of technology. Sometimes it’s as easy as saying, “Hey Alexa, remind me to take out the garbage at 8pm, every Thursday evening.” You can trust her to do whatever you program her to do.


Trello for Productivity

Consolidate To-Do Lists: These can get overwhelming very quickly unless they are all in one place and easy to maintain. Most smartphones come with their own versions of To-do lists, like Apple Notes. I use an android phone and an apple computer, so I need an app that works across all my digital platforms. I have Trello and think it is amazing. There is a free version – which more that accommodates my needs. Using a digital version of a To-Do list means that you can add items on the go and update any items completed. It is always a good idea to save all completed items – just in case you forget whether you did something or not.


When creating your To-Do list use categories: Business planning, Clients, Shopping, Reading, Social, Family, Household etc. When you are in a department store and you can’t remember why on earth you came there, take out your phone, look up your shopping list and you will be reminded why you came there. When you have everything in one place then, if you forget, which you will do a lot of, you know where to look.



You may struggle to make decisions and find it difficult to concentrate well enough to complete even the simplest task. Yet, for an entrepreneur business must go on. Avoid making major life decisions for at least 6 months after a loss or life-changing news. Your perspective and emotional state need to be stable and clear.


But it is the simple decisions that often are the most difficult when you are overwhelmed. You may freeze when trying to decide what to order for a take-out meal, or what supplies to order for the office. It all gets too much, and the choices seem endless and confusing. Create some rules for yourself. This will reduce the overwhelm.


Amazon Echo for Scheduling

Scheduling: It can be difficult to schedule appointments and time with clients or loved ones. You look at your calendar and it all seems a blur. There are so many decisions to make and things to consider when scheduling; time, travel, details, preparation, location, how you feel. So, set some ground rules to help you. These ground rules create boundaries and routines for you so that you don’t get overwhelmed, and avoid making appointments altogether. It can be as simple as telling yourself that you will only take business calls in the morning between 11 am and 12.30noon. This simple rule will give you boundaries both practically and emotionally. Again, when it comes to seeing or chatting with friends, set a perimeter around the time of day and how long. It can seem overwhelming to meet up with friends not just because you are having challenges with making decisions but also because it can be emotionally draining.


These are just suggestions; you will know best what works for you. Regardless, creating such boundaries really help with maintaining the flow of your life. When a friend reaches out for a chat, you know not to schedule it in the mornings and to set a time limit (you can of course go beyond that – this is simply a guideline for when can’t make up your mind).


Putting these empty blocks of time (business calls, business meetings, admin, personal time, social time) in your calendar in advance might also help you with keeping healthy routines and boundaries. It is not that you can’t schedule events outside of these parameters, but it helps reduce the decision-making overload when it is a day that you feel you are carrying a backpack of bricks.



Paper and document management is a struggle for most of us, however, during times of upheaval, it’s even more challenging. You need to have a system in place for paper management. I can’t stress this enough. It is nigh on impossible to manage papers when you are in emotional upheaval let alone make a decision about them. Spend the money early on, on getting someone (GITO Office Organizing Services) to put a paper management system in place for you. If you can’t find what you want in five seconds the method you are using is not working. If you do this early on it will be a fraction of the cost financially and emotionally than doing it two, five or ten years later. Opening old wounds when you have finally found peace is doubly heartbreaking and takes ten times longer to sort (and therefore more expensive).


Document Box

Mail: Nowadays almost everything comes in digital format. However, when you are dealing with the loss of a loved one, a lot of paperwork comes in the mail, and it quickly gets out of control or lost.

When mail comes in, break it down into two categories. One will be “Actionable” – i.e. a bill that needs to be paid, an event that has to be scheduled, a call to be made. Set aside one location, and only one, to keep all your “actionable” mail; it can be a drawer or a box – keep it simple. The other category will be “Filing” – i.e. bank statements, legal documents, cards etc. Again, set aside one location to keep all of your items to file, and don’t make it too big (6 inches deep max). Don’t make it any more complicated than that. You just need to be able to find it. When the filing tray (box or drawer) is full then file everything away (which will be easy because the paper management system you have in place takes care of that). Every day go through your actionable drawer/box and do what makes sense that day to do.



Communicate with your staff. The loss you are going through will also take a toll on them, so it is important to acknowledge this to them and share what is happening in your life. Remaining the same person and leader you were before the loss to your staff is important, but by sharing your journey with them you are allowing some space for you to also be human and feel sad and alone. Now is a great time to learn how to delegate. Trust your staff to support you.


Likewise with contractors, and clients – communicate with them and let them know what has happened. Are there projects that you can place on a temporary hold? Are there clients you can call and delay delivery? It is important to simplify your routines and not work yourself to the bone. By building in time without any obligations you will be more productive at work. Don’t expect the same results that you typically produce, and certainly not in the same amount of time. Take breaks and go home early if you feel the need.



There is no right way to grieve, nor is there a “quick fix”, but there are ways that you can help yourself to stay grounded and move, all be it slowly, through the grieving process, so that, when the time is right, you are ready for a new normal. Find an activity that will ground you and keep you in the present moment. Running, writing, meditating, starting a creative project, or gardening all can help get you into your body into the moment – the place where healing starts. Slowly you will begin to feel like your old self again. Grieving can teach you many lessons, sometimes over and over again, but it does not make you weak, it makes you human.

Survival Tips for Entrepreneurs


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Survival Tips for Entrepreneurs During a Time of Grief

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