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How I launched my business in 90 days 

Or how I went from laid off Product Manager (PM) to career coach, to failed recruiter, to PM coach, to PM consultant, to part time PM, while keeping imposter syndrome in check, to a business owner of chartyourownpath.com on track to replace my full time salary while working fewer hours each week.

May 5

I am laid off from Tripadvisor’s Hotel Product team 

along with 900 of the best and brightest as COVID grinds travel to a halt. I spend a week going through all the stages of grief. I’ll miss the people and the company terribly. Thank you for all the memories.

What do you do when given a chance to try something new? That chance came to me in a post-layoff severance. All of a sudden I had 3 months to pursue something I’ve always thought about on the side. 

With my wife’s encouragement I decide to try something I’ve done on the side for friends and family - help people with their resumes, LinkedIn, and general job searching.

May 12

I launch a career coaching “business” on LinkedIn.

I launch a 1 page lander (landing page) on ConvertKit. My goal is to gather data on 3 questions:

  • Will anyone book a free consult?
  • Will I be any good at giving people coaching advice?
  • Will I enjoy it?

I come off my first two calls absolutely thrilled. This is awesome! I’m so excited to be able to give people advice and help them with their career search and resumes.

My LinkedIn “goes viral” and continues to pick up steam getting 50,000 views. My entire network is super supportive of my new endeavor and sends lots of words encouragement, giving me the confidence and courage to keep going. I spend the next few weeks in back to back free consults talking to people about their job search. I complete 68 free consults, most with people I don’t know but who learned about me on LinkedIn.

Pivot 1

I add a paid 1:1 coaching option

Data in hand for my first three questions I proceed. It’s time to answer my next question:

Will anyone pay me money for my coaching?

I update my one page lander with a link for paid consults (I use Calendly + Stripe) and I start emailing to follow up to my free consults (not Tripadvisor - those are always free) with a link to book a paid 1hr session.

May 24

I have my first paid 1:1 coaching session

One of my free consults converts to a paid 1hr session and I make my first business income! Over the next two weeks I continue to pitch and book paid sessions and gather data. I get over my initial fear that I won’t have anything to offer as my sessions generally go pretty well. People like my advice. Their resumes look much better, the career stories are clearer, and they feel more confident.

I start to ask for testimonials and capture them in a Google Form.

I calculate my free consult to paid client conversion rate is 15%! Yes! Then I crunch all the numbers and realize that there’s no business here. I’ll need to do thousands of consults in order to make back my salary. I have a long argument with my parents who also explain the problem with my non-scalable business.

Pivot 2

I add recruiting services

I decide that perhaps rather than charging job seekers I can charge businesses to connect them to qualified candidates. In theory the math is very lucrative, with % of salaries at stake I can offer my services for free, build a network, and when appropriate I can connect people to jobs. Seems like a win-win, I dream of taking summers off after placing 4-5 candidates each year.

I conduct several customer interviews and am repeatedly rejected. I am told that there’s too many candidates right now in order to consider paying for recruiting services. I try placing for a friend’s company but don’t get anywhere.

Meanwhile I’m continuing to network, and a former teacher and I connect about doing a joint PM coaching product for mid-career professionals to get into Product Management. He works on Sales and closes our first customer.

June 17

I kick off my first Product Manager coaching client.

Nervous, I join my first Product Management coaching session with someone who has spent a lot of money to work with me for several months. I expect disaster, but it goes OK. (A month later her PM story is tight, her resume overhauled, her LinkedIn in top shape, and she’s getting job callbacks.)

At the same time I continue talking to my network and exploring all opportunities. I’m approached by a startup to join in a part time PM capacity. I decide that worst case, if I fail horribly, I burn my bridges abroad (the client’s in Europe). I decide to also pitch a company that had a full time PM role on some PM consulting. Both agree to work with me.

June 22

My birthday & I sign two PM consulting projects

My first client is a software company and I join to help them with their new user onboarding flow. My second client is a hardware and software company and I join to do some research into process improvements that can be made.

The next questions to gather data are:

  • Will I be any good?
  • Can I do this part time PM thing?
  • Will I be any good?

I kick off both clients on the same day (again, my birthday) completely scared. I worry I am a fraud and will have absolutely nothing to offer. My first calls aren’t a complete disaster and I slowly start to understand where I can help.

I continue to network, do free consults, coach, and serve as Product Manager.

June 29

I catch up with another former colleague that opens a new door

I reconnect with a former colleague who adds me to their software development roster for their talent network. Why not?

June 30

I realize my current site’s limitations

Having spent almost 2 months with a strung together website, I ask a friend to give me user feedback on my current site. The main themes she identifies are:

  • Hard to navigate my different offerings without a global navigation and Inconsistent look and feel with multiple landers.
  • Poor control over the primary and secondary CTAs (basically what should the visitor do next).
  • Hard to manage content - testimonials are an awkward block of text, pricing grids are janky, basically it’s starting to look like it’s strung together.

I start to explore several options, and coincidentally catch up with a former colleague who does WordPress site development. I offer to redo his resume if he builds me a simple WordPress site.

July 3

I send out my first invoice

I get paid! *Celebratory dance* I make a mental note to make sure all future clients are good with payment. Prompt payment might become a cashflow issue in the future.

I reflect on my experience with my 2nd client and realize something about myself - I don’t enjoy Product Management consulting. I don’t want to teach or share best practices, I want to do stuff. I make another mental note for future projects.

July 9

I get a v1 WordPress site

I get my first designs back and it looks like a real website! It’s definitely more professional, with top navigation, and a clearer pricing grid… but it doesn’t feel like me.

I try to convey my style - “The design feels a bit too corporate and stoggy for me. I want to be professional but a bit more modern and lighthearted.” But conveying your look and feel to someone else makes me realize I want creative control. I realize that rather than have back-and-forth, and having to rely on someone to make future edits, I should try to do this myself.

July 27

I join the MindTrust talent network and land my 3rd PM consulting client

All of a sudden I’m up to 30hrs of Product Management and am on a track to replace my Tripadvisor income along with the PM coaching.

I join their Product call completely nervous, worried again that I’m a horrible fraud and this will be a disaster. I spend all week ramping up on their product and slowly start seeing opportunities to add value and improve things.

August 3

I hit my 90 day mark post-layoff

Having spent a few days over the course of July building out my new site, I launch my new site to mark my 90 day mark - www.chartyourownpath.com - on Unstack’s platform to reflect my latest business and services.

I pat myself on the back for a minute and enjoy the kudos and thumbs up on LinkedIn. But I’m not standing still, I need to figure out what’s next? How am I going to land new Product Management coaching clients? How will I find fractional Product Management opportunities? How will my site help me with discovery and conversion?

  • Step 1: Blogging & Thought Leadership.
  • Step 2: *shrug*
  • Step 3: Profit!

Let me know what you think of this post by leaving a comment. I’m happy to answer questions and brainstorm regardless of what part of your journey you’re in. And if you want to check out Unstack, you can sign up here.


None of this would have been possible without all of you, my network, and your support. It’s impossible to do a new venture on your own and the emotional, tactical and business support have been invaluable.

Special thanks to John Short - who has been infinitely positive and my mentor. Thanks for showing me that going off on my own is possible. If you need a great marketer check out compoundgrowthmarketing.com.

Special thanks to Shobhit Chugh - who has been a teacher turned business partner and friend. Thanks for showing me how to be tough by asking for what we deserve. If you’re a mid-career Product Manager who wants to get promoted check out intentionalproductmanager.com.