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Ask Robina - July 12, 2023

Robina Bennion
Posted by Robina Bennion on Jul 12, 2023 4:48:07 PM

Hi Robina! 

With all the talk of AI, I am feeling overwhelmed with the technology attached to running my business.  My dreams never included social media, newsletters, automated tasks, and now AI. Honestly, online accounting software was a big leap for me.  Do you have any advice on how to make peace with technology? 

Signed – Feeling Outdated 

Ask Robina ~ Submit your questions here.   


Hello Friend, 

Would it help to know you are not alone?  My introduction to the accounting world started before my first computer and when Excel entered the scene I swore my allegiance to Lotus 1-2-3.  (You don't want stock advice from me. 😊 ) Eventually, I made the switch because it was more efficient.  Since then, benefits have been a key deciding factor in selecting technology to invest in. 

As a business owner, I have spent the last six years flexing my technology muscle moonlighting as a content creator, website designer, and the IT department for my business.  Not the duties people dream of when they start their own business. Especially in accounting/bookkeeping/tax. 

  • The goal of technology is to make our lives easier.   
  • In reality, technology can make our lives busier.  If the right questions aren’t asked. 
  • The Million $ Question... “How do you bridge the gap between your goals and reality?” 

Lucky for you there are programs out there to handle almost all aspects of business but picking one and implementing it can be a full-time job.  Let's explore the integration of technology with you and your business. 

Questions to ask yourself when considering new technology

  • Do you need it?   
      • What is the problem that needs to be solved? 
  • Can you afford it? 
      • How much does the solution cost and how much will it save?  
  • How soon do you need a solution? 
    • Is this a now, soon, or future need? 
  • Is it aligned with you and your business? 
    • Does it make sense for the business? 

Do you need it? 

Just because everyone is talking about it or it seemed like a great product when it flashed across your LinkedIn feed doesn't mean it is meant for you. Part of the overwhelm may be the constant feed of "late-night infomercials" encountered in your social feed, newsletters, etc.  How do you know if it is the right thing to say yes to? 


Questions to ask: 

  • What is the challenge I am trying to solve? 
  • Do I already have tools available that can help me solve this? 
    • If so.. (Be honest here.  There is gold in knowing what the hurdles are) 
      • Why has it not been utilized? 
      • If utilized, why is there still an issue?
      • Does the product solve the problem?

Take your time answering the questions above and ask your team if you have one. If there is anything I have learned as a business owner it is that I can do everything but I don't have to.  You indicated the move to online software felt like a big leap.  Congratulations on taking it.  Moving programs to the cloud frees up time, energy, resources, and location.  There were likely great lessons in the transition that you can utilize in future investment decisions. 

Can you afford it? 

Money can be a sticking point for many people when it comes to investing in technology. Especially, if the outcome is unknown.  Some will go for the cheapest option, other will invest in the highest ticke product without a second thought.  There is no one right answer because each business is different. With that being said, I do believe it is important to not go overboard and buy the most expensive package if it isn't needed now or soon.  The same can be said for the least expensive option as it could cost more in the long run if not properly vetted to match the needs of the company. 

  • Am I ready to invest money into a new solution? 
  • Do I have the financial means to invest now?   
    • If not now, when? 
  • Do I have the energy/time to do this now? 
    • How much of my own time will it take to implement? 
    • Do I have a team or team member to lead the process? 
    • Can I hire someone to assist with the project? 
    • Because I have the money doesn’t mean I have the time.   
  • What will I receive in return? 
    • Or create more “me” time 
    • For example, Would new billing software save your hours and start paying for itself right away? 
    • Will this increase efficiency and profit? 
    • How much of my time will it free up to work on other things? 
    • What other benefits will it provide? 

How soon do you need a resolution? 

With all the fancy gadgets and programs it can be hard to say no to the newest release.  Some people love to get a new phone as soon as it is released and others wait until their old one stops working.  Regardless of where you land, there isn't a wrong answer.  There is only the right answer for you.   

  • If you are slow to adopt, what would help you to take action? 
    • Ask friends what they are using 
    • Do research and familiarize yourself with the bells and whistles. 
    • Let others do the heavy lifting for you. Watch Youtube updates, read newsletters, or check out reviews. 
  • Was the upgrade planned for and budgeted?   
    • If so, follow your plan.  
    • If not, will it create a hardship for you or the business? 
  • If the update wasn’t on your radar… Why now? 
    • Don’t let FOMO drive your decisions.  Embrace JOMO (Joy of Missing Out). 
    • Ask yourself all the other questions before you hit purchase 

Is it aligned with your business plan? 

This may be the first thing to ask yourself.  If you like to keep things simple, procrastinate on newsletters, and rarely post on social media you may want to look at where it is out of alignment.  Maybe it is one component and not the entire process. Don’t fall into the trap of doing what everyone else is doing so that you forget to do what feels right for you.   

  • Am I doing this because I feel like I have to? 
    • Why? 
  • Who do I know that does this like a champ that I can ask the advice of? 
    • Baby steps are easier than big huge giant ones. 
    • How did they start? 
  • Would it align with me if it was outsourced? 
    • For $100-$200/month you could hire someone to do the work for you and make more than enough to cover the cost because you are focused on what you love to do. 
    • If you want to add something to your business (because it aligns with its purpose and future) it doesn’t mean you have to do it all. Someone on your team may love to take on that task. Have kids in your house interested in making some money?   
    • If you deem newsletters or social media important to growing your business but want to focus on bookkeeping, outsource them.   

What’s next…  

Take time to choose right is right for you but resist the urge to do nothing at all.  This could be as simple as following some tech-forward accounting peeps, subscribing to their channels/newsletters, and getting curious.  Be kind to yourself and grow with your knowledge and comfort. 

  • Start slow and get comfortable with the fundamentals.   
  • Gradually add one layer and then another. 
  • Ask for support or training.  A few dollars invested upfront could save you thousands in the future. 
  • Automation can be your friend.  While having your laundry washed and folded with an app may be a ways out wouldn’t it be nice to have your emails automatically sorted and filed for you?   
  • Remember… you don’t need to automate every aspect of your life.  If you are a paper and pen kind of person consider a good old-fashioned paper book or buy some new pens to take notes.  Ideas can be born with pen and paper. 
  • Continue to stay curious.  You never know what may happen… One day you could be on the cutting edge of technology. 

Thank you for using technology to reach out and ask your question.  Do keep in touch and consider submitting an article for The Woodard Report column on the next hardware/software purchasing experience. 


With Gratitude,


Robina is a Certified Money Coach and retired CPA.  She works as a guide for people to discover the freedom to dream again by transforming their relationship with money. If you want to know more about Robina, you can visit her at 

Do you have questions about MONEY?  It may not feel like it but deciding what to do for your business, career, or on a personal level is often entangled with money.  So, let's make money a part of the conversation.  If you are facing an issue at work or company, you don't know how to solve and don't want to talk to anyone about. Ask it here.   

....  Ask Robina Submit your question to Ask Robina HERE! 


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