5 Questions Every Entrepreneur Should Ask for a Daily Check-in

Linda M. Lopeke
4 min readNov 14, 2020

Sales metrics aren’t the only measure of success.

Image Credit: Outer Digit on Unsplash.com

Having a daily check-in ritual can help you stay on course even when things get rough.

Every day I see a great many program pitches and product launches purposely designed to sell false hope in my inbox and social feeds. Worse, it’s often those who can least afford it getting caught up in the hype. With devastating results.

But sales metrics aren’t the only measure of success.

Real success brings joy and happiness to your life as well as revenue to your business — if you manage your relationship with it well. To that end, the quality of the questions you ask yourself at the end of each day can greatly influence your results on all fronts.

While you should monitor the key performance metrics that tell your business story, asking yourself these 5 key questions each day will help you keep it all in perspective and continually moving forward toward the vision of success you most desire.

Many of my clients and students do this daily review just before sleep but when you ask the questions is up to you. Establishing this daily habit in the first place is what is most important.

QUESTION #1: What am I grateful for?

No matter how difficult the day has been, there are always things to be grateful for. After 9/11, for two years, I kept a gratitude journal, writing down 3–5 things I was grateful for before bed each night.

An unwelcome life change had been forced on me at that time and I had two young children I had to stay strong for while literally everything else collapsed around us. The commitment to making those journal entries kept me going.

Then, in 2009, a life-changing accident happened taking along with it my ability to write, think, remember. To be honest, for years afterward I was not all that grateful about surviving.

But, I continued to make a daily effort to look for something, anything I might hold onto, however inconsequential, small or tenuous it seemed. Proof old habits die hard.

And while there were many days I couldn’t find a single thing beyond the possibility of death to focus on, I kept looking. Maintaining an attitude of gratitude despite one’s circumstances is not easy, but it is worth fighting for.

Now, although I only note them mentally, the answers come more easily. And I can assure you, even if this was the only question you asked yourself at the end of the work day, it’s powerful enough to transform your entire life (and with it, your business).

QUESTION #2: How do I feel?

We all understand the importance of maintaining good physical health. Our mental health is equally important and must also be a priority. Because, if we aren’t taking care of ourselves, we eventually might become unable to take care of business.

Asking this question helps us find the friction points we encountered during the day that we need to look at and eliminate. There can be a great many of them. As you get rid of each one, you’ll feel lighter and lighter. Rid yourself of all of them and your life will change immeasurably. Guaranteed.

QUESTION #3: How much stress did I experience?

Sometimes friction points interrupt the smooth functioning of your day and the cause, once identified, can often easily be corrected. When the friction point is a person though, it can take longer to make the required change. But still, it must be done.

There may be times when we are the cause of our own stress because we are one big walking, talking friction point ourselves. Such situations can be even more challenging, but need to be fixed too. Preferably first.

QUESTION #4: How did I make others feel?

It costs nothing to practice random acts of kindness, to give credit where credit is due, or to share a kind word and a smile with someone who might need it. We never really know what burdens others carry.

What I do know is, looking for ways to help others feel good about themselves, their work and their day is the fastest way to improve your own. Don’t miss opportunities to contribute to others’ lives in a positive way whenever you can.

Doing this for those who can’t do anything for you in return speaks volumes about who you are — bonus points for that!

QUESTION #5: What did I learn today?

Every person you meet knows something you don’t. Every day brings with it new opportunities for learning. Including, no especially, through our failures. There is no growth without learning, personally or professionally. Use what you’ve learned to have a better tomorrow.

Bottom line? You don’t have to be perfect! No one is. Successful people resist false hope and embrace what is. Keep asking these questions as part of your daily check-in routine and listen carefully to your answers.

Do more of the things that make you smile and less of the things that don’t. Make someone else’s day better. Experience the beauty that exists in the daily ordinary. And, above all, keep a grateful mind and humble service-oriented soul. Asking yourself these five questions every day keeps you grounded and far less likely to become a prisoner of false hope.

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