When I bought bagels at our favourite bakery the shop was empty. So I started a chat with the store manager. She asked about my day and what I was doing for work. When I told her I run a career coaching business and work with data and tech professionals, she asked “Do you enjoy the freedom that brings?”
I loved that question and nobody had asked it in that way before, so here is the detailed version of the answer I gave her (in addition to replying YES):
I’ve been learning a ton of stuff I never expected
Yes, I speak with my clients, coach them, provide tools and frameworks and contacts. But running a business involves so much more that I initially didn’t consider.
I had to and enjoyed learning a lot more about marketing, selling and picking my very own set of tools to work with. All of this continues to be ‘work in progress’, but going from a fortnightly newsletter to five emails a week and growing my readership (YOU!) to over 800 is something I am proud of. As is creating workflows, automations, email sequences and other stuff that I previously only ever heard about from digital marketing colleagues.
Making an effort to show up as me whether I speak on stage, post on LinkedIn, send a follow-up email or show up as a podcast guest has been a nice challenge. Not living up to other people’s expectations or definitions, but deciding how I want to tell my story and share my ideas and creating the voice to do that in.
I really like selecting the right tools to work with. I used to wonder why some companies have such a mess of disconnected data sources that proliferated over time. Now I know 😆. The enterprise level stuff is EXPENSIVE, so you start scrappy and try to scale it from there.
My current selection includes Google Business suite, Notion, Kit.com, Folk, Xero, Claude, Slack, Zoom, and Stripe.
I have 100% flexibility in how I work
It’s a blessing and a curse, yes, but with a small child it’s mostly a blessing.
I never have to ask for anyone’s approval for taking time off, attending a conference or choosing my work location.
Before this sounds all too glamorous, I have to balance it by saying: time off can impact sales and revenue and the future pipeline. Attending a conference isn’t straightforward unless they’re virtual or local. And choosing my work location is usually a question of coffee shop vs kitchen table vs garden office. Because going to co-working spaces would require a 30min commute, which given my working hours isn’t sensible 😊.
But the flexibility is there and even working during a Friday evening has its appeals. Because I do it for ME and for my family.
What helps is noticing when I do my best work (an exercise I invite every new client to do as well!), so that I can choose the right setup based on the tasks on my list.
I love that flexibility and I love not answering to anyone. I can go on holiday or I can work during a trip to see my relatives. And when I have fewer hours available for work, I can squeeze them into my evenings and coordinate parenting and client calls with my partner.
It’s very satisfying to be responsible for my success and performance
Satisfying and sometimes daunting. I want to focus on the positive aspects in this email, but I need to at least mention the pressure that comes from being responsible for generating your own income every single month.
I don’t have ‘retainer clients’. My goal is to support clients so they feel fully equipped and confident to move ahead in their career without me, once our sessions are done.
I have a few clients who have returned (some even more than once) to continue working together on new goals or to have an accountability partner for their ongoing success. I love that! The majority of my work, however, is with new clients every few months.
Finding them, getting to know them and showing them how I can support them is a very satisfying part of my work.
I’ve come to appreciate this a lot more over the last year. Looking back at the progress I have made (rather than purely focusing on the goals ahead) and recognising that I did almost all of that myself, with input from my own coach, as well as the admin support of Elaine and our accountant, that feels good.
It’s very different from my time as an employee. Even when I had bigger things I was responsible for, they always depended on other people’s approvals, contributions and expertise. That is totally ok. I now enjoy this new level of completely owning my work. It also means I get to decide what I want to work on and how I do it.
The freedom to just do it
Other business owners have told me similar things. They love the freedom of having an idea, giving it a go, launching it and seeing the results.
There’s definitely a ‘recommended’ way of going about it, e.g. including market research etc. But the space to say “I have an idea” and turning it into something tangible without blockers, that’s the stuff I enjoy.
If it’s helpful, here’s a specific question I have for you: if you were to start your own business, what’s the biggest improvement to your life that you’d expect from this shift?