The subject that always comes up


Maddie Tudor Consulting

Lesson Learned: Insights From an Entrepreneur Trying To Figure It Out

The Main Event

One problem seems to be a perennial issue for myself and my clients: Doing something for yourself is so much harder than doing it for someone else.

Whether that be marketing, grant writing, graphic design, or any other expertise, we can all seem to use our talents for others much easier than we can for our own work.

It’s something I tried to address in my first-ever newsletter, and it has been on my mind for even longer. Unfortunately, I’m not here to report a breakthrough, but I am here to try to tease out an answer a little bit more.

I sit here writing wondering, how can I help us all get unstuck from that spot?

For my clients, a lot of the time I’m able to take a task on for them as much as they’ll let me (and that’s a big caveat). But when they are bullish on doing it themselves, I find myself suggesting all sorts of things. Just a few of the solutions I’ve tested out are:

  • Using project management software and breaking the task into smaller pieces with deadlines
  • Suggesting they try out the Pomodoro Technique for an hour of total work and see where they get
  • Having them work on the issue while I’m on the phone with them, there to answer questions or help them when they get blocked

These have all worked to varying degrees depending on the person. All are valid answers to the issue and ones that I’ve also employed for myself.

But, the more I think about it, I realize this block seems to come from a deeper place—doing work for ourselves can expose our soft underbelly when we put it out in the world, so much more than when you do it for others.

How is it more vulnerable than doing work for clients? For one, when I work on client projects, I’m often writing in their voice or an approximation of it, and I expect changes and feedback. Here, there is no other voice, only my own and I have to suddenly stand behind it more than ever before.

As I’ve mentioned before, Brene Brown teaches us that vulnerability is the key component to courage. But how do we work up that courage? I’ve written before about a few answers, having a village to support you chief among them (going back again, to my first newsletter).

As I sit here now, having written 28 of these newsletters, and turning 30 in under a month, I can’t say that I’ve solved this problem any further, but I have found that the best way to make that vulnerability less scary is practice.

The more I write, the better I get, and the prouder I am to share my work. Instead of hiding in fear of sharing my words, now I’m sharing them as widely as I can. That strength comes with time, too, as that thick skin so many talk about continues to develop.

Despite all of that, I’ve found in many ways, my writing has gotten more vulnerable in tone. I can only chalk that up to courage, and it’s something I’m thankful for, as I think it’s a key part of my voice.

So, no, I don’t have a solution or exact answer to how to help this problem. Instead, I suggest you dig deep, and try to find that inner spark of courage.

Lesson Learned: Some answers or solutions may remain out of reach, but the longer you work at something, the more strength and courage you build. You learn to let go of fear, and that’s all we can ask for.


My Current Obsessions...

What I'm Burning: Windows Down by Henry Rose is bringing in spring for me with hints of ozone and floral notes. It’s not available as a candle anymore, but it is as an eau de parfum, which I would totally wear!

What I'm Watching: Like many right now, I’m so excited to have Top Chef back on. While I do miss Padma Lakshmi as the host, I still love it and always will.

Wild Card: I’m convinced that we non-gamers are really missing out on some brilliant storytelling by not playing games for whatever reason. My solution to that is watching playthroughs on YouTube when I hear a game is brilliant. The latest one blowing my mind is Stray Gods, a storytelling musical game where your choices drastically change the story, and yes, I did just say that. I highly recommend you check it one in any way you can.

Speak Soon!

P.S. Did what I wrote resonate with you? Great! If you would do me the honor of passing this on to anyone else you think would like it, I would really appreciate it and subscribe if you haven't already! Plus, make sure to take me out of your junk folder!

10100 Galaxy Way, Los Angeles, CA 90067
Unsubscribe · Preferences

Lesson Learned: Insights From an Entrepreneur Trying To Figure It Out

Get insights from a marketer turned entrepreneur straight to your inbox every other week. Catch up on previous Lessons below and sign up to receive future editions!

Read more from Lesson Learned: Insights From an Entrepreneur Trying To Figure It Out

Maddie Tudor Consulting Lesson Learned: Insights From an Entrepreneur Trying To Figure It Out The Main Event I was recently enjoying my nightly scroll through TikTok when I stumbled upon a user who was starting a fresh account with only one goal in mind: to read all of the books on the brand-new 100 Best Books of The 21st Century from The New York Times. She’d already read book 100 and not enjoyed it, but was so far having a better time with book 99, Bel Canto by Ann Patchett (no surprise...

Maddie Tudor Consulting Lesson Learned: Insights From an Entrepreneur Trying To Figure It Out I recently wrote a guest article for my friends at MemoryFox on tools to level up your social video game. If you're interested, check it out here! The Main Event It’s that time of year in the U.S., a time that so many in our nation dread, yet is also so important: election season. It’s a time that seems to divide so many of us, but I want to think about something that unifies us all. Our system is...

Maddie Tudor Consulting Lesson Learned: Insights From an Entrepreneur Trying To Figure It Out The Main Event Alas, today I write to tell you some news: I’ve come down with a fever. Not just any fever, but one that shall last a month and afflicts me every two (or four) years. I kid, but a lot of us may be feeling this way right now as we sit and enjoy the Paris 2024 Olympics each day. But it isn’t as simple as that anymore, the Olympic sports have lept from our screens and grown larger, taking...