Dear Ruchi, Tax time always brings up so much anxiety for me. I run my own business so things aren’t as simple as they used to be when I simply had my corporate paycheck. To be honest, I never know where to start when it comes to getting organized for the filing deadline. Do you have any advice as to how to prepare? Next year I want it to be seamless with minimal stress. I am ready to make a change!
Dear Ruchi, I really love being self-employed and freelancing has given me a brand new outlook on my career. Though I am happy, the financial aspect can be tricky. From month to month my income can vary by a lot and sometimes I worry that the inconsistency will put me in a scary place. How should I be planning for the future, saving for emergencies, etc. when I’m not always sure what my bank account will look like each month?
Dear Ruchi, I am SO bad at managing my money and always have been. Being a business owner, this makes everything feel 10x harder. It’s so hard to run a business in such a crowded market and I feel a lot of fear and stress when it comes to dealing with budgets, finances, and making smart money moves for the future. I want to break out of these habits, so I can set myself and my business up for success. Where do I even begin when I feel like I have dug myself into a deep dark hole? Help!
Dear Ruchi, I am in the very early phases of starting my new business. I am concerned that I am not setting things up “properly”. I always thought opening an LLC would be the only option for me but I have heard several different opinions.
Dear Ruchi, I have spent over 15 years working in the corporate world and feel it is finally time to pivot into my true calling. I am seriously considering leaving my job and starting my own business. This is a big jump and I am very nervous. As I inch closer to taking this leap, what is the best way to financially plan as I get started? What should I consider before jumping ship?
Dear Ruchi, last year I had an incredibly high tax bill that I was not prepared for. I was SO shocked and still quite frankly don’t fully understand how taxes work for a business owner like me. I don’t want to be in the same position this year and need some guidance on how to avoid this in the future.
Currently, my business is small enough that I use spreadsheets to keep track of things and do everything manually. As I grow, how should I think about my bookkeeping? What should I automate first, what tools should I consider?
Dear Ruchi, as a business owner I often find myself managing just about everything. Being so busy, I worry I am not accurately tracking my books and managing my finances properly. Plus, to be honest I always become a little paranoid around tax season and worry that I am missing something important. When do you know it’s time to hire/outsource your bookkeeping or financial management if it’s not your core business?
Dear Ruchi, I have an old client invoice that I am just realizing was never paid. Is there a way to get a tax deduction on this? What should I do?
Dear Ruchi, this is my first official year as a business owner. I am getting worried about tax season even though it is many months away. When it comes to anything accounting related, I instantly feel stressed and confused.
Before she worked with amazing, heart-centered, fun-to-work-with service-based business owners like you… Ruchi spent almost two decades as a senior executive in the financial services industry. Now as a seasoned financial guide and mentor, Ruchi is often also referred to as a “financial therapist”. She is the Founder and CEO of Watch Her Prosper and is committed to empowering business owners to achieve a life of total prosperity.
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