Hey Reader!
Two weeks ago I told you I’d like to continue to transform this newsletter to a format that directly serves you as a leader and founder. I asked for letters from subscribers about a business or leadership challenge you’re currently facing. I got a great first batch, certainly enough to get started.
So this week please enjoy the first of what I hope will become the standard format here. “Hey B!” is my version of Dear Sugar or Dear Abby, but for leadership, entrepreneurship, and making an impact at work.
If you have a challenge you’re facing, hit reply to send me a letter and I might use it for a future newsletter!
Let’s get to it.
Letter from a Founder
Hey B!
I’m about to leave my long-time job leading marketing at an established software startup to become a founder of a (solopreneur) company that offers fractional CMO services to software companies in the $1M – $50M annual revenue range.
I plan to launch in August after I take a little time off. I joined a Fractional CMO accelerator program which starts this summer and I’m sure that will be really helpful but I know I’m about to go on one hell of a career adventure.
We have +/-1.5 years of financial runway without touching long term assets, but I can’t help but worry if I have the emotional runway to make it too. I was dealing with some pretty significant burnout and other old wounds at my last job. I don’t want to jump in too quickly but I also don’t want to wait too long either.
My core question is: how did you navigate the transition out of ConvertKit to building your own business? Any advice to navigate that transition well on a practical or technical level? What about the emotional level and even things that may have impacted your core identity?
Thanks!
A Talented Marketer Venturing Out On My Own
Hey, A Talented Marketer,
Thanks so much for being a guinea pig in my little experiment to turn this newsletter into the Deer Sugar of Entrepreneurship and leadership.
First of all, whether it’s by choice or by force, I’m really sorry you’re leaving a job that has left you feeling burnt out and tired. I’m sure you have given everything you have to the role, and any role or company is challenging no matter how needed the change was.
I don’t think my process of leaving ConvertKit was perfect. Could any process like that be perfect?
But I do think I learned a few things about what I needed and what is helpful along the way.
I have a short list of questions for you:
1) Have you properly grieved?
This might seem like an odd first question when talking about leaving a job and starting a business. Longtime readers of this newsletter will have seen me talk about grief in these lines before.
We don’t talk about grief enough in western society, and especially not in the United States. We think grief is what happens when someone dies. And it is, but it’s also what happens at many other crossroads in life. Leaving a job that was important enough to you to burn out over is one of those crossroads.
Have you grieved yet? Have you cried about all that you’ve lost as you make this transition? Have you said the things you needed to say to your boss and coworkers, but couldn’t because of your values? Have you written all the hard things down on a sheet of paper and burnt them in a fire while you cry over how hard it felt along the way?
You have to grieve the loss of things that matter to you. If you’re anything like me, your job very much mattered to you.
A book you might pick up to help process the grief of this ending so that you can start fresh is called The Wild Edge of Sorrow. My friend Andy Crissinger recommended it to me when I was in your shoes and I was very grateful he did.
2) Are you full or empty?
I’m sure there are many legitimate reasons to jump right into an accelerator and start your business a couple weeks after you leave this job.
I have one question for you when you get on the other side of that short break that you’ve planned on: are you feeling full or empty?
Two weeks after I left my job as a COO, I’m not sure I had ever felt more empty. I hear that you’re going to take some time off. It’s probably the first time you’ve taken that much time off – truly off – in a very long time.But what I know now looking back, is that I wish I had taken more time truly off.
No agenda, no scheming, no planning for the future. Sit in a park and stare at blades of grass. Take a hike in the gorge outside of Portland. Get my hands dirty in my garden. Sit and stare at my young boys to appreciate how small they are — the smallest they will ever be. Spend quality time with my wife. Visit a bookstore and pick a book off the shelf for no other reason than that it sounds fun.
I know it seems like a few weeks off will be a lot. Perhaps it’s enough. But I think you’ll have the best chance of building a successful business if you give yourself the rest of the year to do nothing. Sometimes the best way to go fast is to go slow.
3) Is the excitement or fear more present?
I didn’t mention this before, but about a week and a half after I left ConvertKit, I jumped into an all volunteer project to make a book with a mentor.
I thought “if I’m going to reinvent my career to combat climate change, I better start building a believable portfolio.”
In reality, I was scared of sitting still. I was scared of becoming irrelevant. I was scared that if I didn’t get started immediately, I wouldn’t never have opportunities again.
So I’d ask you: is the push to get started… Is the concrete plan to do fractional CMO work… Is the accelerator… Just a way to try and bury fear? Or is it because you’re excited?
When you find the excitement again, you know it’s time to get started.
4) Are you aligned with your partner and family?
You didn’t say this in your letter, but I know from our conversations about whether it was OK to publish your letter that you have a family.
One of the great mistakes I made in starting my first business back in 2011 was that I wasn’t fully aligned with my then girlfriend, now wife. It wreaked havoc on our relationship for years and took a lot of intentional effort to rebuild trust around me being an entrepreneur.
When I left Convertkit, we did it together. We both knew what was happening, we knew the plan, and we agreed to it.
Does your partner know the plan? Do your kids? Do they know what to expect during the time you’re taking away from work?
Once you start building the business, how many hours is it OK for you to work? How many months are you comfortable going before you move to Plan B? What does success look like? What old patterns do you want to make sure to avoid in this transition?
If I were back in your shoes, I would want to be as explicit as possible about all of the above and much more with my partner.
5) Back up plan: If ______ is not true by ________ I will _____________.
Speaking of Plan B… What is Plan B?
Back when I started that first business, I believed it was irresponsible to have a Plan B. Burn the boats, don’t look back, the only way out is through.
Now I know that was a mistake. You’re making an investment in yourself by starting this business. You are your own venture capitalist. And the limited partners in your fund are your partner and children.
You and your partners need to know what losses you’re willing to take to have a chance at the upside of a successful and fulfilling business… And you need to know when the losses are too high and it’s time to move on.
What are the circumstances under which you will move on to Plan B? How long will you work on this business? How much of your savings are you comfortable using? How much revenue do you need to be earning by what date? And if you aren’t earning that revenue by that date, what is the plan? Will you begin applying for jobs? Will you raise money?
Write the plan down. Sign it. Have your partner sign it. Have your children sign it. Put it in a drawer for safekeeping and don’t look at it again until the date by which you need to have achieved your goal. Hopefully you’ll never need it.
6) What old wounds have not yet been healed and how will they show up in your new business?
I wish I could tell you that entrepreneurship fixed all of my flaws. I wish I could tell you all of those patterns that created burnout and sadness and grief for me after leaving ConvertKit went away once I was on my own.
It will surprise no one to say that none of the above is true. I had to work through all of those old patterns that were creating pain. I used coaching, therapy, coach training programs, deep conversations with my wife, challenging conversations with friends, and so much more. These tools helped me confront all of the things that led to me leaving the company and losing my identity in the process.
Your patterns will follow you too. No job can fix them. No amount of business success as a founder can fix them. There is no one else in your life that can fix them for you.
The patterns and habits and beliefs and old stories that created the sense of burnout and pain that you are experiencing as you leave this job will continue. They will exist until you confront them, understand and accept them, and integrate new ones into your life
This process is independent of what you do to make a living. That’s the most important work of your life. Your partner and children will benefit from it. So will your future clients and employees. But no one will benefit more than you.
Make sure to prioritize this work just as much as you prioritize the work of your new business.
Much love and respect,
PS: Things to do next:
- Hit reply and write me a letter about a leadership challenge you’re facing. I might answer it in an upcoming newsletter.
- Listen to Michelle Tam on how building a food business empire has shaped her life and work.
- Forward this newsletter to a friend who would enjoy it
- Refer a founder friend to coaching and I’ll pay you $1,000 if we start working together