Hello, wherever you are in the world I hope this season is bringing you some well-deserved relaxation time and you feel proud of making it through another year in your entrepreneurial career.

Before I let you in behind the scenes, let me first take the opportunity to say a huge thank you to readers of this newsletter for your ongoing support, time and engagement. It truly means a lot.

Highs of 2022

As I’d encourage you to do in your own reflections, let’s begin with the highs.

Travel.

In 2022 I decided to take my life and business remote and travel the world. From Portugal to America, the Canary Islands to Columbia.

Working for yourself removes any need for permission when it comes to choices like this. The life of a ‘remote nomad’ was not always easy, and came at a cost to business growth and my bank balance, but was entirely worth it. Every life decision is a trade off and I’m pretty sure this turned out to be the best year of my life. Highlights being the people, adventures, learning Spanish, performing Improv in Chicago and lots of dancing. Some snaps… 📷

This newsletter.

Writing what I know and care about and finding like-minded people along the way — this is more than just a newsletter to me. Here I meet coaching clients who want to figure out what’s next in their entrepreneurial career and find the tools to make it happen, I get sent opportunities for collaboration and meet friends along the way.

Today 3,150 of you are reading, which is 3x more than last year and open rates remain at 50%. Here are the most popular newsletter posts of this year.

• How to carve a career path on your own terms

• How to plan your year ahead (through career uncertainty)

• How to find more clarity in your work

Talent to Money (T2M)

Talent to Money was an online summit I hosted in June to help people on their first steps to launching a business around their talent. We attracted speakers including Khe He, Josh Spector, Sharmadean Reid, Wes Kao, Stef Sword Williams and Sari Azout and the feedback from the attendees who wrote to us and gave 5* reviews. Over two days 760 people attended live.

By far the biggest project of my life and took months to organise but I’m immensely proud of the work that myself and three freelancers Mel, Nas and Erin put in whilst also running a fully booked coaching business. It was a busy time and I learnt a lot not just about online events, but about personal growth, stepping outside my comfort zone, managing my time, team leadership, brand building, hosting panels and sales.

Not all of these lessons were profitable (as I’ll explain) but regardless of its outcome, we put on an incredible event that truly helped attendees in their path to generating income from their ideas.

Coaching

The Ask® first and foremost is a coaching business and I am extremely grateful to coach the smart, curious, ambitious entrepreneurial professionals I do. This year, clients have pivoted their businesses into new industries, taken on CEO roles, created new companies (14 in fact!), been hired for dream roles and built brands and audiences around causes they care about.

Challenges of 2022

From a professional perspective, this summer was a challenge. I’d been sprinting towards a set of goals for six months that I hoped would materialise sadly none did.

After some wallowing, I launched into an objective assessment of the whole business.

A big realisation: we’d been so focused on coaching people at the start of their entrepreneurial journeys, forgetting that there are so many other ways these same people can be helped: business mentors, startup accelerators, investors, education, courses and subject matter experts. All viable solutions to the same problem.

I’m not afraid of competition but I am afraid of competing in the wrong race.

Providing business-building tactics was never the ‘why’ behind starting The Ask. It has evolved that way following some advice I’d been given to choose to coach either founders OR employees, and I’d chosen early-stage founders. There was resistance at the time but I couldn’t put my finger on why, and also knew I didn’t want to choose a specific type of founder to coach either, e.g ‘how to become a coach’ or ‘VC-backed founders’, given my firm belief people should discover their unique flavour of work and not copy the methods of others and expect the same results.

So this summer I took a step back. It evolved into three long months of reviewing everything, which meant cutting back on all expenses and sales efforts. It struck me that I had originally started The Ask based on the common problem I noticed in my career in headhunting and talent consulting as well as my personal experience of two career changes.

So many people are stuck and indecisive about what their professional path should be — stuck choosing between the myriad of options that exist.

Also, upon viewing the data, the clients I both enjoyed working with the most and who had the biggest transformation had two things in common: they were very ambitious, and they were confused about the path ahead. Often due to too many options, negative work experiences, burn-out or lack of role models, many smart people can’t decide on what they want the next phase of their career to look like. They crave clarity about their professional direction, and as we know this is the exact problem I got into business to solve. Boom.

But how can I incorporate my years working with startups and founders I thought?

Entrepreneurial careers.

By solely helping people who work in ambiguous, entrepreneurial environments, or who are building their own. We live in a fast-evolving career landscape and I want to be the coach to guide people through it.

Today’s world isn’t either or entrepreneurship or employment, it can be both and.

These environments inherently lack direction, clarity and clear steps to take. This kind of coaching will help you with a bespoke roadmap to take, based on you. For employees with an entrepreneurial mindset or entrepreneurial ambitions or side projects… this is about figuring out the best mix of working for someone else and working for yourself. Or if you know you want to be your own boss, it’s figuring out a roadmap to make money on terms that work for you and suit your talent.

Sessions cover three core pillars to a career pivot: clarity, planning, and action. The Ask’s signature coaching programme, A New Direction ensures clients who work with me will get crystal clear clarity on decisions before launching into the potentially wrong job application, business model or pivot.

We dig into skills & strengths, motivations and drivers, past experiences, future dreams and then setting clear goals & timelines. But essentially, it’s about doing the thing not just talking about it. Every career pivot or new business idea in an entrepreneurial environment is about choosing yourself. No is one coming to save you.

As your Coach, I hold you accountable for doing the hard thing and take the risks that feel scary or vulnerable and require a little coaching and motivation to overcome the procrastination they inevitably bring up. Sending that cold email, putting yourself forward for the role, launching that sales campaign. And provide edits or feedback along the way. Clarity begets momentum.

After sharing this new niche, September was my best month in business. A special thanks to an online training programme for coaches building businesses that helped me to rebuild the foundations again.
— If you’re a coach and want the details feel free to email me

The books, people & tools that shaped the year

• For Digital Organisation
  As The Ask and my life got more complex I shifted entirely to Notion for life & business organisation. For notes, project planning, task management and more. If you’re a business owner and need help with Notion-based automation and clear systems, speak with Daniel Canosa who helped me build a bespoke operating system. Check out his services & book a consultation here.

• For Learning
  My content diet has focused on business building, careers and psychology. Helpful reads include Michael Gerber’s The E-Myth, for building repeatable, reliable systems. Jenny Blake’s Free Time to improve your business operations for .. more free time. I loved Anything you Want by Erik Sivers for life and business lessons, same with The Almanack of Naval Ravikant especially the advice on strengths. Newsletter-wise, a shoutout to Alex’s Basic Arts and Divinations (both on business strategy), Josh Spector (building an audience) Femstreet (careers & tech) and MKT1 (marketing).

• For Client Management
  After reviewing everything, I’ve found a better system for leads, bookings, diary management, contracts, messaging, to-do lists & files for clients and emails — solving a lot of my administrative needs and rolling out in the new year. If you’re running a coaching business can so far highly recommend Practice. Sign up here.

• For Writing Online
  I loved Steph Smith’s ultimate guide to Doing Content Right which shares everything she knows about creating, writing, and scaling successful blogs and newsletters to millions of readers — highly recommended.

What’s to come in 2023

Products & services in the pipeline and how you can get support with deciding, planning or taking action in your entrepreneurial career.

• On Monday, January 9th I’m hosting a small group through a powerful 2023 Vision & Goal Setting session in 90 minutes to help you both decide what you want to happen in 2023 and set milestones around it. Attendees of this year’s had many career & personal wins they’ve since reported back. Tickets here.

• Talent Profiling & Strengths Testing. You can book a one-off session with me to analyse where you are (and aren’t) using your strengths in your entrepreneurial career, with opportunities to tap into them further. More info & bookings here.

• Creator Day in Poole. Mark from You Are The Media has invited me to speak at Creator Day in April. If you want to spend the day focused on your content and message and becoming the leading voice in your industry do get a ticket!

• Videos, newsletter changes & memberships. You’ll be able to access more support from The Ask by way of video content, with YouTube, courses and newsletter changes around the corner TBA very soon!

• Coaching more ambitious, entrepreneurial professionals decide and plan their next career pivot or business idea so they can feel clear and excited about their future through coaching & mentoring, apply for personalised coaching here.

If you made it all this way to the end — I’m honoured to be able to carve out this community and your attention amongst a sea of content online. I don’t take showing up in your inbox for granted and in 2023 will be back with more guidance on finding the right professional path for you in a world that is only becoming more and more entrepreneurial world.

Thank you as always for reading!

Ellen Donnelly, Founder + Chief Coach, The Ask.