Buyer's remorse on your life?

Did you achieve your dream life and realize it wasn't actually your dream?

My first major purchase with my own money (that I remember) was a board game focused on cows… to be honest, that’s about the extent of what I remember about it.

I played it maybe twice ever and was generally kinda meh about it. Buying it was a big deal for me, because I, as a little kid, saw it in the store and told my mom I needed it.

Teaching me a life lesson, my mom told me that she’s wouldn’t be paying for it. But if I wanted to save up my allowances I could buy it myself once I had enough. This became my mission, one-track mind, laser focus, I may have even pitched for extra chores to get a bigger allowance. Because this game was obviously going to change my life.

Billie Eilish Obvi GIF by megan lockhart

Gif by meganlockhart on Giphy

Weeks later, I purchased the game and weirdly no one else was excited to play it (it’s like they knew some secret I didn’t … it wasn’t a good game). I would never admit it as a kid, but I learned rapidly that their intuition was right. A board game based on the lives of cows has rather limited entertainment value.

I was so focused on the goal that I never stopped to ask if it was a good goal for me - would I enjoy what I was so diligently working towards?

As a core memory for my relationship with money (and delayed gratification), you’d think I’d consider this 20 years later when making major life decisions.

In college, all the jobs, successful people, and opportunities I was interested in were in corporate America. So I worked backward: successful corporate job → great resume → high ranking graduate degree → 2-5 years of high-impact work experience → great undergrad GPA.

And just like that I planned out the next 5 years of my life. Starting within weeks of graduating from undergrad I took the GMAT (MBA school application test).

5 years later, I got a job in corporate, we moved to Chicago, I had an MBA & MSBA (if one is good, two is better… right?), and I worked in big Pharma. Except I was quickly learning I hadn’t taken enough time to think about if I had been chasing the right goal. Day to day, I didn’t enjoy it and to my chagrin just like my cow board game, my mom had questioned if I wanted a corporate job - maybe my mom sometimes know me better than I know myself…? (Nope, not touching that)

Sport Mma GIF by UFC

Gif by ufc on Giphy

Looking back, these experiences could have been saved by looking past the “shiny cover” and focusing on the functional details a little closer before setting it as my North Star guiding my decisions.

That’s way easier said than done.

We worked with a coaching client this week who was i) looking to gain clarity on positioning two of her brands, ii) what the offers she’s promoting, and iii) what content to create around them over the next 1-2 months.

Before we started coaching, our questionnaire included 3 important questions to get to know her, so that we could continually evaluate if she would actually enjoy the options we’d be discussing or end up with “buyer’s remorse” as soon as she started applying anything we discussed.

  1. In the past 6 months, what tasks/projects have put you in a flow state (lost track of time, felt energized doing them, could do it all day long and be happy)?

  2. In the past 6 months what tasks/projects have been drainers (put them off forever, throw off your whole day when you have to do them, put you in a bad mood, block happiness)?

  3. 12 months from now, what would be your ideal day/week? What are the things you’re personally doing / responsible for?

If I had gone through these questions when I was job hunting in grad school, I could have seen fairly quickly that the job I accepted wouldn’t check the boxes for me. It’d look roughly like this:

Flow state

  • Applying knowledge to problem solving in unique and out of the box ways - my job was a subject matter expert, sitting in meetings explaining how things worked

  • Working on a team to collaborate on ideas - solo subject matter expert, not really any “team” in singular expert

  • Educating other people and helping them improve - about 5% of my time was teaching, mostly it was sitting on meetings saying 10 words about a technical working of our data lake


  • Having no clear impact - big pharma I was ~15 layers from an actual patient…

  • Pointless busywork - “cog in a machine” vibes, lots of weekly reports preparation type stuff

12 months, personally doing?

  • Helping people solve difficult problems - this is a mixed bag, everything we were doing was big difficult problems, but sitting in 10 meetings to change the structure of a database schema didn’t really check this box for me

  • Personally seeing the impact of what I’m doing - see “cog in a machine”

  • Challenging people to be the best version of themselves - to be fair having my own intern checked this box, but by that point I was already planning my exit

What became shockingly clear to me when I started thinking in the context of questions like this, I knew immediately that what Jo was doing working with small business owners was a much better fit for me. I lasted exactly 12 months in corporate and then joined Jo.

So how does this apply to you?

Next time you’re debating adding a new offer, pivoting to a new niche, or outsourcing a core capability from your business, think about these three questions. How can you increase time in your flow state, remove drainers, and set the goals that you’re working towards in a way that aligns with that?

Just because someone you look up to/follow told you the “best” way to do something, doesn’t necessarily mean it’s the best thing for you. Put another way, if you’re willing to spend thousands of dollars on a vacation to make you happy for a couple days, would you be willing to take a different route in life that could make you slightly less money (today) but create infinitely more happiness every day?

See you next week,

Ps if you don’t even know where to start, hit reply (or DM on IG @joandlyndon) and we can talk about any coaching offers that may fit your needs.


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