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The Key to a Successful Big Life Transition

Wouldn’t it be great to transition seamlessly between phases of life?

To efficiently switch from one path, to the next, with no loss of productivity in-between?

From a logic standpoint, we might plan our life like this – trying to maximize results and minimize downtime – but unless you’re Spock, your life is likely to differ from whatever cold, logic-driven plan you might put together.


At least that’s how it’s been for me.

After ending a long-term relationship earlier this year, I moved to San Francisco to live in a co-living house with a bunch of hackers and do-ers.

Product Den co-living

My original logic-driven plan was to create multiple minimum viable products (MVPs) and then double-down on one that got some traction with users.

After moving in, I began testing a number of business ideas. A parent certification program, an anti-cold product, and BuyBlocker – a free Chrome extension helps you save money by hiding “buy buttons” on Amazon, eBay, Walmart, etc.

I worked out of the 500 Startups (Venture Capital Accelerator) office downtown.

And when not working, I made new friends, explored the Bay Area, and worked out as often as possible.

Also, I read books. Many more than I have in the past few years.

That’s all well and good. But now it’s 6 months later and I don’t have a single business idea I’m married to. The reality of my situation deviated from the plan.

Let’s take a step back for a second…

In 2016 I had a clear purpose: to start a business.

That business ended up being my book Debt Destroyer, along with the email list and companion site that I setup.

In 2017, my purpose has been – essentially – a search for a purpose.

It’s been a transition period. And it’s not over. I’m still transitioning.

But along the way I’ve discovered some things that helped me find purpose, clarity and meaning. I’ve also found ways to address some of the rougher parts of this type of change. I’ll share them below.

I’ve also found plenty of things that did NOT help. I’ll briefly mention those for you to consider as well.

The Key to a Successful Big Life Transition

Before we get into this too deep, let’s first define what we’re talking about here.

When I say “Big Life Transition” – what jumps to mind?

Changing careers?

Having a sex change operation?

Becoming an adult?

In my case, I ended a serious long-term relationship earlier in 2017 after a year of traveling overseas together. Since then

Today, let’s define a Big Life Transition as:

  • A change in your life
  • Which involves new goals, behaviors, or environments
  • And likely involves re-considering your future

Ok, so think about it.

Is there anything going on in your life that you might fit this definition?

Maybe you’re already knee-deep in a Big Life Transition.

What big efforts are underway in your life?

Ok. Now that we have a working definition, why do we need to talk about this at all?

The Good and The Bad of Big Life Transitions

This may be oversimplifying, but in order to have something to clearly discuss here, let’s add a little detail to our understanding of Big Life Transitions.

The Good

  • A Big Life Transition is an opportunity for personal growth. Face with new challenges, you must rise to the occasion and find solutions. For example, a new career may involve learning new skills, or acquiring new resources (knowledge, relationships, etc.).
  • Hopefully you’re advancing along the path of life. Many transitions of this nature are steps along the path towards a better future, a better you. Maybe you’re having kids, or getting married. In either case, you’re taking steps towards a future you desire.

The Bad

  • Big Life Transitions can be emotionally taxing. Life gets more complicated when you start to change up the variables. Behavior patterns, routines and habits you’ve developed over the years may no longer be relevant. This can be incredibly stressful.

I’m sure I’m missing some points here, but let’s keep moving along.

It seems clear that the Good is worth the Bad (hopefully you feel the same way about whatever you’re dealing with).

But that doesn’t mean we shouldn’t try to minimize the Bad, eh?

So how do we do that?

Making a Big Life Transition as Smoothly As Possible

Here’s what I’ve learned during the past 6 months of my Big Life Transition. Yep, you read that right. Six months. Not a quick change by any means.

#1. Ask questions. Don’t stop asking.

Good questions are the beginning of good insights.

Develop a habit of asking yourself thought-provoking questions on a regular basis.

If you have satisfying answers, great! You’re on the right path, keep moving.

If you find your answers lacking, dig deeper. Write your thoughts down. Write a hypothesis and then test it. Consult friends for alternative perspectives.

Here are some of the questions I’ve been asking myself:

What do I care about? What am I willing to struggle for? Why do I do what I do?

What do I value? What makes me happy? How can I position myself to be successful for the next 3-, 6-, 12-months?

What are the underlying assumptions behind this Big Life Transition?

What’s the best case scenario? What’s the worst that could happen?

#2. Focus on the next step. Don’t worry about much beyond that.

“Go as far as you can see right now. Don’t worry past that. Once you get there you’ll be able to see farther.”
– J.P. Morgan

There’s only so much you can handle right now. And you need to focus on something.

Big Life Transitions may involve many steps, but you have to complete the NEXT step in order to advance. So focus on that.

If you spend too much time on future steps, you’ll slow your progress on (or may never get to) the next step.

In my case, I sometimes struggled with the potential “impact” that my business projects had. Always the nagging doubt of this isn’t BIG enough.

Or, how will I handle confusing Step #5 after I get product-market fit?

This type of thinking was the entrepreneurial equivalent of shooting myself in the foot. And I don’t recommend it.

#3. Reconnect with what matters.

What do you value?

Family? Friends? Personal time? Self-improvement?

What makes you feel alive?

Recently I’ve been tracking A) the things that inspire me, and B) what makes me happy.

I now know that watching Elon Musk interviews inspires me. I also know that singing makes me happy. And weirdly, cold showers make me laugh.

I know that a great workout makes me feel invincible. After pushing up the final hill, suddenly I feel like anything is within the realm of possibility. It’s only a matter of effort.

This self-knowledge is valuable.

I can strategically incorporate these things into my day to combat anxiety and stress.

If you find fulfillment in family time, make time to spend with family.

If you feel grounded with friends, make plans and keep them.

Remember why you’re doing the Big Life Transition at all. Whether you’re making a change in your business, relationship, or home life, or something entirely different, chances are it’s ultimately in the pursuit of these core, foundational elements of life.

What Big Life Transition are you dealing with? Why is it important to you?

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