My 5 Step Process for Figuring Out What is Next

Read time: 10 minutes

Welcome to The Ascend Archives Tuesday Tale, a weekly newsletter where I share a story about a transformation, revelation, or change in thinking that has helped improve an aspect of my life.

FYI: Today’s newsletter is longer than usual. It’s very tactical for anyone who has had the thought “What should I do next with my life?” If that’s you then this might be interesting. If not, no worries!

Last week I sent a voice memo to my business coach Patrick, “Dude I’m starting to feel like you. I had 3 conversations this week with guys trying to figure out what to do with their lives. Before I knew it, I was coaching them up and asking the same questions you asked me 6 months ago.”

The guys I was talking to weren’t kids right out of college either. It was two 25-year-olds questioning whether it was time for something new, a 29-year-old father in a high paying consulting job, and a guy in his late 50s trying to figure out his next 5 year runway into retirement.

These are some of the thoughts they had:

  • Not feeling fulfilled in their current jobs

  • Looking for cash flow to replace their income

  • Feeling it’s tough to leave a high paying job that pays the bills

  • Wanting to be surrounded by like-minded people

  • Not knowing what else they want to do

I'm no coach or expert, but I did have those exact thoughts last November. Now 6 months later I have clarity to answer many of those questions. So I figured why not explain the work I did with Patrick that has helped me get here?

Turns out these guys found what I had to say helpful. So I decided to distill some of the highlights in today’s newsletter for anyone else struggling with the daunting question of “How do I figure out what to do with my life?”

1. Change my mindset from need to want

This subtle language change has been eye opening. I never realized how much I said the phrases "I need to" or "I should".

For 3 months, I met with Patrick every week. Each session would start with me giving an update and calling out what I want to discuss. As I would start rambling about everything going on in my life, I would subconsciously say those phases. Every time I did, Patrick would call me out.

Example One

Me: “I’m trying to decide whether to keep my Chicago property and rent it out or sell it. I should probably keep it because the interest rate is so low and I can make $500/month renting it out”

Patrick: “You should keep it or do you want to keep it? Just because the interest rate is low doesn’t mean you have to keep it. What if you took the money from selling the property and invested in something else that paid you more than $500 / month?”

Me: “I didn’t think about that. I’ll run that analysis and look at what aligns with my values”

Example Two

Me: “I need to post on LinkedIn every day if I’m going to grow my audience. But I’d prefer just writing my newsletter”

Patrick: “Why do you have to post on LinkedIn every day?”

Me: “Because that’s what the algorithms require for me to grow so I can get more people to sign up for my newsletter”

Patrick: “Well why do you need to grow your audience”

Me: “Hmm well that’s how people monetize the newsletter, but my goal right now isn’t to monetize the newsletter. My goal is just to consistently publish and improve my writing skills. I’m going to stop posting on LinkedIn for now”

These are just two of dozens of examples where Patrick challenged me. Now I catch myself saying need or should and I challenge myself. It helps me get down to the root cause of what I am actually trying to achieve.

Shifting to this mindset of I want to do X just because has been freeing. He encouraged me that I don't need to justify anything in my life to anyone. I want what I want because I want it. And that’s totally ok.

2. My ideal day/week

Once I had the wanting mindset, we started to get tactical. If everything was on the table what would my perfect day look like? Not my dream vacation or the popular perception of retirement sitting on the beach doing nothing. But think about what I would want a typical Tuesday to look like.

I focused on the general activities that I would be doing and not on the specifics (e.g., job role, location, etc.)

There are two ways to go about this exercise:

Ideal day

I planned my day out to the hour. Here are some questions I pondered:

  • What time do I wake up?

  • Do I start work right away, sip tea with a book, or workout?

  • Do I go into an office, stay at home, or go to a coffee shop?

  • Do I want to work independently, am I taking phone calls or meeting with clients, am I speaking on stage, or am I leading team meetings?

  • Does my morning look different than my afternoon?

  • What do my evenings look like? Is it date night with my partner, basketball practice with my kids, or trivia night with friends?

  • Am I reading a book or watching my favorite show before bed?

Here is one version of my ideal day:

  • 5 AM: wake up, journal, read daily stoic, meditate, drink a smoothie

  • 6 AM: workout, sauna, cold plunge, and mobility

  • 730 AM: writing block at coffee shop

  • 930 AM: walk outside by the lake or ocean

  • 1030 AM: work on my business (emails, operations, brainstorming)

  • 1 PM: lunch with a mentor or while listening to a pod

  • 2 PM: team meetings, collaboration with business partners

  • 5 PM: wellness activity: golf driving range, pickup bball, yoga, or massage

  • 630 PM: date night with girlfriend

  • 9 PM: gratitude, read, plan for next day

Ideal week

It was tough to plan just one day because I’m not going to go on a date every night. Or maybe I want to go to travel half the week and be home half the week. That is where the ideal week comes in. It’s a similar exercise of focusing on general activities but gives me more flexibility to include a variety of items.

Here is an example:



The idea is not for these to be perfect, but it’s to get me thinking about the types of things I want to be doing. Would this weekly calendar excite me or stress me out? Compared to my old calendar working a corporate job…it’s night and day.

3. Define my values

The next step is getting clarity on what is important. I already had defined my values but I revisited them with Patrick.

What are 5-6 values that I want to live my life by?

The first time I tried defining my values I had no idea where to start. So I used this list from James Clear. I went down the list and highlighted everything that resonated with me (15 items). Then I compared the 15 and prioritized what felt more important until I got down to 5-6 which I felt strongly about.

I use these values and the questions I created as a filter for my decision making when it comes to what business opportunities to pursue, people to surround myself with, and generally how I decide to spend my time. The list has evolved slightly over the years, but this is where it is now.

  • Adventure: Does this excite me? Will this be memorable?

  • Growth: Does this help me improve in a certain way? How?

  • Authenticity: Is this aligned with what I think, say, and do? Is this something I purely want to do or are there external factors influencing me?

  • Contribution: Who is this helping and how does it help?

  • Relationships: Do I enjoy being around this person? Is there trust with this person? In what area of my life is this relationship beneficial?

4. Brainstorm list of everything I could do

I did this exercise focused on what type of business I wanted to pursue. But it can be done generally for how to spend your time. I sat down and just wrote everything that came to mind that I might want to pursue. Nothing was off limits.

Start a non-profit? Travel the world and blog about it? Become a YouTube star? Invest in real estate? Play the guitar? Write a book? Get a 6 pack?

After I had a massive list, I used a set of questions and the filters I previously worked on to refine it and determine what to focus on.

For each item, I asked:

1. What excites me about this and why

2. What is unappealing about this to me and why

These questions helped me go beyond the surface to really understand what I like and dislike.

For example, buying a small business was on my list.

Exciting part: It wasn't as risky as starting my own business and I could use my consulting skillset to improve a boring business like a plumbing company or car wash. It seemed achievable and would help me replace my income.

Unappealing part: Buying a small business was location specific so I couldn’t travel. I don’t know if I want to work with people in boring businesses and I might not find something in an industry that interested me.

This taught me that I’m not ready to bet on something super risky, I’d like to use my existing consulting skillset, I value flexibility to travel, and I want to work with high performing people.

By doing this reflection for each idea, I learned more about what I wanted and it became apparent why some of my ideas had to be removed from the list.

5. Start experimenting

This is where I am currently.

Paul Graham, founder of Y-Combinator said, “We truly don't know what we like or dislike until we try it.”

My filters helped me prioritize but at the end of the day, I will never know if I'll actually like buying and owning a small business until I try it. It’s not reasonable to just go buy a business, realize I don’t like it, then sell it. But there are ways to run small experiments to test these ideas before fully committing time & money to them.

I can talk to people doing the idea, shadow them in their work, or start my own mini projects. Some of my experiments included:

  • Analyzing small businesses for 2-3 weeks

  • Writing every day on Twitter for a month

  • Writing newsletters twice a week

The key is not being afraid to quit or "fail" at these experiments. The first two I realized I didn’t enjoy so I quit. You could say I failed to buy a business or be consistent with posting on social media. I’ll take it because those failures got me closer to what I do enjoy: writing newsletters.

I change my mindset to that of a scientist. They have experiments in the lab that fail all the time. It’s part of the process. The goal is to run as many experiments as possible and reflect on what is working and what is not. Then, slowly we can piece together the activities, business opportunities, relationships, etc. that get us to our ideal week and in alignment with our values.

Final Thoughts

This process doesn't happen overnight and isn't completed in one sitting.

I owe a lot of credit for my progress to my business coach Patrick. Having someone who had gone through this process himself and knew what questions to ask was key. It accelerated my process vs if I tried doing this all alone.

He called me out on my language, helped explore different business opportunities, and was a sound of reason when I started to get imposter syndrome, doubt myself and stress about the fear of the unknown and judgement. He pushed me to continue on the path and I’m so glad he did.

Now I'm in a position to do the same for others. I still have a long way to go but I have learned that we all have knowledge to share. There is always someone 2 steps behind me in something that can benefit from my experience. That’s what makes sharing knowledge so powerful.

I’m excited to see where these mini coaching sessions go and am pumped to be on the journey with these folks.

Thank you for reading! As always please reply and let me know what resonated, what didn’t, or what you question. I love chatting about this stuff!