Lessons Learned from Starting Over After Success

The second time is harder even when you have the blueprint.

Starting over is hard. Especially when you’ve been successful in the past. Screw all the “enjoy the journey” talk. You did that last time and don’t wanna go through it again. You wanna pick up where you left off and reclaim your seat at the table, along with everything that came with it.

The gift here is that you have the blueprint. You know how to be successful because you’ve done it before. You’ll crush the obstacles that previously slowed you down, and sometimes there won’t be obstacles at all because you’ve planned ahead based on your past experience.

But because you have the blueprint, you know this’ll be a lot of work, and it’s gonna take time. It doesn’t help that you feel like your peer group is half way around the track, and you’re just starting the race. So instead, you do nothing because the weight of having to follow all these steps again is overwhelming. And then you beat yourself up about it even though you know that’s counterproductive.

Oh you overachiever you! *pinches cheek*

Starting over can really do a number on your confidence. I know because I was there when I pivoted from writing about dating and relationships to podcasting about personal finance and career growth. I was there when I went from a two-man show to a one man booth. I was there when my engagement ended in 2017.

And I was there for years before I started training to get back into track and field

Coincidentally, training has turned out to be the best teacher. It helped me overcome the stuckness again recently. I’d been trying to fire up the content creation machine for months and it was more like our faulty PS5 that randomly shuts off in the middle of games. And rather than try to fix it, I just stop playing the game altogether.

This happened repeatedly with my podcast and there have been several iterations of this Substack that only the cache gods will ever know existed.

Now I’ve fixed the machine and taken my first few strides. I can still feel the mud hugging my feet, but it’s not strong enough to inhibit the next step. I’m ready for the long haul.

Here are four things that training taught me that helped me defeat Inertia.

Focus on one session at a time (OSAAT).

When I’m looking at my training program, I’m not thinking about next week’s sessions or the new phase that starts three weeks from now. My only goal is to get through that single workout. Doesn’t matter if it’s short or long.

This applies directly to starting over. Don't make the hurdles taller than they need to be. Focus on the next step. Send one email. Make one connection. Complete one task.

Don't worry about what you need to do a week or a month from now. Just get through today. Use AI if you have to. Whatever it takes to help you complete the session. Then acknowledge yourself for what you’ve done. You already know these little wins are bigger than you think.

Accept that things will go wrong and plans will get derailed.

Sometimes I get to my training session later than planned and have to cut exercises from the workout, or I have weeks like last week where I intended to complete five training sessions, but my body only allowed me complete three. Here’s the generally applicable lesson I keep in mind:

The universe doesn't care about your plans.

Your carefully constructed comeback will be derailed. Life will happen. The launch will get pushed back. A project will stall. A connection won't pan out. Shit will hit the fan when you thought you were finally in the clear. And that's okay.

Since you’ve been successful before, you know that setbacks are part of the process. They're not indictments against your identity; they're simply hurdles to be cleared. When you accept this, you welcome resilience and getting off-track becomes less demoralizing.

Identify your success conditions.

If you know your success conditions, you can build an even better blueprint.

When you were thriving before, what was going on for and around you? Did you feel a certain sense of energy or calm? What parts of the journey were most rewarding? Was it the fact you were constantly learning and overcoming new challenges?

I noticed I’m at my best as a content creator when I’m consuming the type of content I create. The best part is that it doesn’t take much. I was listening to a mindset podcast this morning and one sentence was enough fuel to help me get this post across the finish line.

I also know I have the most creative energy and complex process power in the AM. So before digging into anything else, I either work on content or the most urgent and challenging project of the day. If I don’t feel moved to do either of those things, I read or listen to something to move me in that direction.

Accept that you can’t control the timing.

I put a ton of pressure on myself for my first indoor championship meet in 2022. It was my first indoor championship meet in 15+ years. At 38, it felt like I was running out of time to hit the performance goals I’d dreamed of. And if I didn’t do it that first season, it would get further and further away until it was physically impossible.

That meet didn’t go as hoped (obviously). I was both embarrassed and disappointed afterward. I wished I hadn’t told anybody I was training or that I was at the meet. It felt like I disappointed people who in reality were happy to see me doing something I enjoyed.

Then I had another heart-crushingly poor performance in the long jump at the outdoor championships, before I came back the next day and won my first national championship in the triple jump…in the rain!

Patience is the hardest part of starting over because you know what success is like and can’t wait to get back to your version of it.

But as I’ve learned over the past few years, you can’t control when the big personal best will happen, when you’ll get that email, or when the right person will see your work. You can only control your mindset and process.

This time, try to embrace that lack of control. Instead of being focused on the result, you can focus on the story. Every step, setback, and small victory is part of a new one you're building.

Imagine what it’ll be like to tell it after you accomplish this goal? If you’re like me, that thought makes you feel something. Hold on to it, because that’s what this go-around is all about.

R