1+1: Build a longer on-ramp + Discover your next career with AI

Here's one leadership idea and one resource I’ve found beneficial in the past two weeks:

1 idea: Build a longer on-ramp

My blood pressure rose steadily as I pulled my Camry into my parking spot. “Don’t you trust me?” I asked rhetorically, defensively.

It was the spring of 2019. On our joint commute to work, I’d casually mentioned to my wife that I was ready to quit my job and become a full-time entrepreneur. I’d take my side-hustle of coaching and consulting and go all-in. It would be magnificent. There was no way I could fail.

“Ok…” Emily responded slowly, tentatively. “So, how is that going to work? How are we going to have health insurance?”

With a one-year-old at home and plans for a sibling soon, she wanted to know how we’d afford doctor’s visits for our growing family. My answer was simple: we’d quit both of our jobs, move to Fort Wayne, and restart there. We could move in with her parents to start. My business was already growing, and it was bound to take off once I gave it my full attention. 

If her head was spinning at the suddenness of my plan, I didn’t notice. I’d been thinking about this for months and had analyzed every angle. All she needed to do was agree, and all of our dreams would soon come true.

“But how will you get business?...How much will you make?...What do we even need to make?” she asked as the logistics of my idea started to crystallize in her mind.

I felt irritation building inside me. I tried unsuccessfully to hold it at bay. “Don’t you trust me?” I asked accusingly.

***

When I tell people about my entrepreneurial journey today, they often say, “Wow, that must have been so scary.” My reply every time is, “Actually, that wasn’t the hardest part. Convincing my wife was.”

At the time, Emily’s questions felt like a damning indicator of her disbelief in me. But now I realize that questions were totally valid. She wanted to support me and also wanted to care for our family. The problem wasn’t her doubts or my dreams—it was the decision-making process I’d unintentionally used.

Because I’d spent several months thinking through my ideas, my plans were fully baked. I’d already overcome my doubt and fear to reach full commitment. But because I hadn’t shared my musings with my wife, she was totally blindsided. She had to grow through the same adjustment stages that I’d gone through months ago and was not eager to revisit. She also wanted some say in the future of our family. But because the plans were fully formed in my mind, I wasn’t interested in changing anything. I didn’t want to re-bake the cake; I was ready to frost it.

Had I shared my thinking along the way as I mulled over my plans, two good things would have happened. First, I would have been more open to my wife’s feedback because my plans were less set in stone. I had less to lose at that point; the concrete was still wet. Maybe we could have even crafted a shared future instead of me just trying to get her on board with mine. And second, my wife would have more time to adjust to the idea along with me. We could go through the stages of adjustment together.

The core idea here is simple: the bigger the change, the longer the on-ramp.

If you’re changing the type of copy paper you use in the office, that's no biggie--just notify people in a Friday memo. But if you’re changing your team’s strategy or KPIs or compensation structure, you’d best invite your folks into that discussion sooner and give them more time to adjust to the new reality.

This principle is especially true in family settings where trust, interdependence, and transparency are even more critical. If you want to make a big change that will affect others, share your ideas as they develop in bitesize pieces along the way. If you roll out a sweeping change as I did, they’ll feel compelled to throw on the brakes to slow the runaway train. The conversation will turn into an Us vs Them battle. But if you build a longer on-ramp, your loved ones will have valuable insight for you. And if they love you, they’ll want to root for you rather than against you.

Eventually, I unbaked my cake. With Emily, I analyzed our budget to figure out how long we could make it. We set up monthly budget meetings to review our progress. We built contingency plans and found part-time work to stretch our money even further. And eventually, she felt good about the plan. We made the leap together, and it worked—but not as smoothly as I originally thought it would. Had I not let go of my defensiveness and trusted her wisdom, the business likely would have failed. Although slowing down was painful for me, the collaborative process we finally discovered enabled my business to get up to speed in a sustainable way—and crucially, made our marriage stronger in the process.

***

• What ideas are you dreaming up right now?

• When is the right time to share them with the people you trust?

• How could you invite their honest feedback and use it to make your plans even better?

1 resource: Discover your next career with AI

If you are dreaming up your next career as I was, check out this AI tool from Google called Career Dreamer. It provides a low-stakes and highly interactive way to explore different outlets for your strengths and passions.

PS: Now, that was a good surprise…