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Pocket Project Turns One 🎈

To me, one year sounds like a short amount of time but it feels like much longer when it comes to Pocket Project. But, I still remember getting excited over coming up with a name and questioning if I would actually go through with this endeavor.

There are quite a few things that pushed me to pursue this, but largely it is the support I’ve always gotten from others. I was never met with skepticism or negative thoughts when bringing up the idea of starting a business for myself - so for all those who supported me, thank you.

I never pursued this for the clout - I never call myself a CEO, a founder, an owner, etc. I’ve always called myself a financial planner and tax preparer - it is what I love doing and what I see myself as. I wanted to have total flexibility to plan in a way that I think is the best for my clients and makes me feel like my most genuine self. That is what drove me to start Pocket Project.

So, here I am one year later. Like all the cliches, it has been a rollercoaster. I think reading about others’ entrepreneurial experiences can often give a false sense of what to expect if pursuing a similar course of action. This is survivorship bias - those with huge success want to tell the world all about it, and those who “failed” or had a much slower start are reluctant to share their stories - leading to a lot of success to read about, and all the slower / failed businesses to go unseen.

I would describe Pocket Project as “a much slower start” - not a raging success financially, but also have the ability and motivation to keep going. Here are some of my thoughts I’ve collected around my specific journey so far.


Working for yourself is hard! I sometimes miss the days of having a boss to tell me what to do, and moving assigned projects forward so that I can feel good about collecting my paycheck.

It is not quite the same when starting a business. Not only am I responsible for moving everything forward, but at the start of a business you have a lot free time. What do I even tackle first?? What are the most important tasks to complete right now to set myself up for success? I still have to balance these priorities, and I suspect that will continue for a long time.

It also interests me that my expectations of this endeavor turned out much different than reality. I was willing to make this plunge because I am confident in my ability to know and understand financial and tax laws / strategies and my ability to listen and understand others.

I thought the hardest part for me would be getting clients and the easiest part would be the process of giving advice… which turned out to be the opposite. I am far from swimming in clients, but getting my first few was easier than expected. The hard part ended up being creating processes, using updated tech, finding meeting cadences, how often to check in with clients, etc. It is something that I will always be changing and adapting to suit my clients needs - this is hard because there is no clear answer and everybody is different.

In this whole endeavor, I have had to start putting myself out there, which is not something that comes naturally or comfortably to me. Creating content, talking about my business and how I can help others - it feels like other advisors are SO GOOD at self-promotion… honestly, I am glad I am not, but it would probably make getting clients a bit easier.

In order to get myself out there, I started creating content around finance and tax topics, but there is a whole internet full of everything I already talk about - I would often think, “who cares what I think or have to say?” I still have these thoughts occasionally through my imposter syndrome, but it has been encouraging to see some traction with my content.

Everything has been coming in waves, which creates many lows and many highs. I’ve gone months without the hint of a prospect, and months where five show up. It is something that will likely continue and I’ll have to get used to.

Long story short, this has been hard but I am focusing on enjoying the journey and seeing what comes of this. What is most important to me is being responsible with anybody that entrusts me with their finances or taxes, and at the end of the day I can feel good with whatever happens knowing that I responsibly helped others.


I think there are plenty of businesses that (in a positive way) explode right off the bat and entrepreneurship was the best choice for the owners. Unfortunately, those are the only times something makes the media or gets shown in podcasts, articles, etc. It can create unrealistic expectations and can bring down others who are on a similar path that don’t have the same outcome (hence my comment on survivorship bias).

Fortunately, starting and running a financial planning business is not too expensive. I bet many would be shocked how little it actually costs to start and run one. It’s probably why there are so many bad actors in the industry, capitalizing on lack of financial knowledge from the general public - there are low barriers to entry and somewhat inexpensive. You just have to come off as trustworthy to others!

The much bigger costs to starting a business is just paying for my lifestyle! I still have to have shelter, a car, health insurance, food, ongoing entertainment, etc., which all has to be funded without a paycheck (until that “paycheck” is built). I don’t think it is worth becoming an entrepreneur if you are going to destroy your standard of living for a few years (no matter what @markcuban suggests in Shark Tank).

I feel fortunate that I am in the business of financial planning because it has really helped me to prepare for and make this leap to self-employment. On top of that, I don’t feel AS bad about spending my money that I worked hard to save over my career, because I know how to save money and I know I’ll be okay in the long run. My biggest concern is making my current funds outlast my lack of income, until I make enough to support my lifestyle.

I definitely still feel bad at times though - every month that goes by, another few thousand dollars out of my accounts, it feels like I am fighting against a clock. It starts to make me question every purchase - do I deserve a vacation right now? Will this ruin my chances of “success”? Can I comfortably live in the desert with my AC set to 80?? It is interesting to start to see what expenses are a trigger for me and which aren’t - it has helped me to grow and understand some of my money behaviors.

To give a little view into my last 12 months, I’ve collected about $11k of gross revenue, with expenses outweighing that by a few thousand. This is largely start up costs for a computer, designation fees, compliance consultants, state registration, etc. At this point, I am running at a profit each month and hopefully this continues in an upward trajectory.

I’ve seen my savings account go down about $40k over these past 12 months. I’ve been supplementing my spending with part time tax work with TurboTax during tax season, which I am ready to do again this coming season.

As a financial planner, I can’t help to think that not only have I spent down $40k, I also gave up an entire year of income in my 20s. Certainly not ideal, but I am viewing this project as one of my biggest investments into my happiness and future flexibility in my career.

Also, as a slight paradox for somebody in the money profession, I am far more motivated by fulfillment as opposed to money. The impact I felt I’ve had on some of my clients, knowing that I can take my time and listen to them as opposed to seeing clients as numbers and revenues, it has really made me feel a lot better about what I am doing and the financial planning industry as a career path for me.

Final Thoughts

In a world of immediate gratification, tech company explosions, meme stock mania, crypto, etc., there are endless get rich quick schemes. In my opinion, that is not what starting a business is about. What is the fun in get rich quick?? The true fun for me is making a difference for others and solving something that brings me purpose - not just commas in my bank account.

Starting a business is not just about financial growth - it is also about personal growth. I’ve always told myself since starting Pocket Project that the worst that can happen is I have some new experience and learned how to run a business. I still believe in that and will forever take that with me.

So, I have one year behind me and I am hoping for many more! But more than that, I am really looking forward to continuing to learn and improve my craft as a planner so that I can better help others.


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