Being Your Own Boss: Figuring Out What To Do and How To Do It
This is the first in a four-part series.
Six years ago, I set out to work for myself. I wasn’t a famous personality, I didn’t have a personal brand (I really despise that phrase) and, most importantly, I had absolutely no idea what I was doing, nor what I really wanted to do, besides make enough money to call it a living.
That is precisely why I’m sharing my experience.
Because I’m an average person. Because there are similarities to my arc and others’ solo journeys. Because, while my approach might not apply precisely to where you are at in your career, the lessons learned throughout my evolution may be beneficial.
“Success is liking yourself, what you do and how you do it.” Maya Angelou
As noted, I didn’t have a clear plan. I cast a very wide net, one which reflected the breadth of experience and knowledge I’d built over two decades. People who knew me professionally, knew what I was good at, so I leaned into it by identifying four subject matters I had competency in
Business Intelligence & Analytics
Data Management & Governance
Change Management
Leadership Development
It was through this broad-strokes approach that I learned what type of work I did – and did not, want to do. But let’s not get ahead of ourselves.
What You Do
Let’s look at that short list again. Inside an organization, people get to know what you are good at and passionate about. As an employee, it was not unusual for me to be an IT Manager and deliver leadership training. However, the connection between the four areas I identified is not as obvious to potential clients who have never met me.
That forced me to get creative, to ensure I demonstrated the interdependencies and overlap. For about three years, I kept all four subject matter areas in my business. Being the data person I am, I made a spreadsheet of the work I was hired for: the subject matter and the delivery type.
After the first two, two-and-a-half years I noticed that the areas of expertise I was hired for, the What, was fairly evenly spread across all four.
What jumped out at me, upon reflection, was what the data points, and my emotions were telling me, when I looked at the list of delivery types.
How You Do It
This is an important determination to reach when working for yourself.
You get to choose the work you want to do. For most of us, we only know what we think we are capable of when working for someone else. Once those restrictions disappear, the real education begins.
When I set out, I split my offerings into three different delivery modes: Public Speaking, Facilitation and Consulting. The usual trifecta for talkers and trainers.
Since my experience with public speaking is mentioned in part two of the series, I’ll skip over it here.
I discovered I love facilitating workshops. It’s the inner teacher in me, I suppose, to enjoy the uncertainty and excitement of walking into a room full of strangers with a clear goal of achieving a breakthrough.
Some participants are eager to learn, some would rather be at work and some are voluntold to be there by their organization. (We’ve all been there) They have no idea who I am or what to expect. It is truly thrilling to witness the shift in attitudes over the course of the session.
While I know it will happen, I don’t know how it will happen.
Mirroring my experience as a professor, I’m equipped with far more material than will be used. Examples, activities and content that will never see the light of day. The overall arc of the session is planned. The outcomes are determined. How we get there as a group, is unique.
While I am leading the session, I’m determining the level of trust between members of the group. Are there simmering tensions preventing attendees from engaging with each other? Which activity is going to serve this particular group best? What style of delivery is most effective?
The spontaneity of human nature is why I enjoy it. In a workshop, I’m the person who needs to adapt and I need to adapt in front of a live audience.
Like so many others, I also tried consulting.
On the surface, consulting is a natural extension of the large project work I’ve been doing for years as an employee. Turns out, the experience was too close to being an employee for me.
The role of an outside consultant is necessary for organizations that simply do not have the niche expertise in-house. There are excellent consultants out there, I’ve worked alongside some incredibly talented and effective professionals.
It simply wasn’t a great fit for me, even with my experience implementing large scale projects.
Being an embedded consultant means attending to all aspects of a project within their role, while being onsite at an organization. I started to feel a lack of control over my schedule, which was part of the lure for going solo. Juggling multiple clients at once and ensuring I secured the next client, was manageable, though a little uncomfortable. That discomfort grew when client demands started creeping later into the evening and on weekends.
It felt more akin to being an employee again, only this time, there were four or five bosses whose demands were increasing.
I want to be clear. The situation I found myself in was positive. I was working. I had clients. The engagements grew less exciting, and what I valued most, control of my schedule, was diminishing.
After completing work for my tenth client, I reflected on my consulting experience as a whole.
Was it was the role, the types of projects or the clients themselves that I did/did not enjoy?
For me, I mostly enjoyed the clients and was lucky to work on some genuinely interesting projects (with a great opportunity to learn about different industries). The dissatisfaction stemmed from the type of work.
I understood this because I gave myself ample experience - AKA data points and variables. I didn’t give up after one poor gig.
There was another benefit of waiting until I had enough consulting work to truly reflect. A new opportunity sprang out of my consulting clients: facilitating stakeholder consensus sessions.
Unlike workshops, these meetings are specifically designed to bring together multiple stakeholders participating in an initiative, often from different organizations or from various divisions of a large company. In that role, I serve as the objective third-party.
I work with the parties to determine the rules of engagement; drive ideation sessions or improve and formalize how the stakeholders communicate. Typically, I facilitate (see referee) challenging meetings where there is seemingly no agreement to be reached – and help them move past that roadblock in order for the initiative to succeed.
Hence, stakeholder consensus.
Truthfully, I had never considered this role until I found myself being explicitly hired to perform it by my consulting clients. They saw that I could bring value to their organization in a completely different role, one that I enjoyed and may never have recognized on my own.
Further proof to try on new hats, and not give up immediately if you have one bad gig. You never know what tree will grow out of that seed.
Now vs Then
Casting the wide net served its purpose.
Then: In the first-round of me going solo I explored all I thought I had to offer.
Now: The second round is where I trimmed off what didn’t work for me and introduced new elements that did.
The What. Those four areas of expertise shrank to three: Communication, Change Management and Leadership Development. Change Management is communication. So is the throughline for most Leadership Development elements.
Data & Analytics are limited to a couple of workshop offerings. Stepping away from the one thing most people identified me with was difficult, but also felt as though a heavy weight was removed. After several decades in the field, I simply did not wish to do data work anymore.
I was hesitant to let go because I was still thinking like an employee. It felt like quitting.
I had to remember I was the business owner. If you truly do not enjoy something, that negativity will surface, either with poor results for the client or by taking an unnecessarily draining toll on you.
It doesn’t matter what you do, it matters how you do it.
You won’t fail to notice how much of this essay was devoted to the How vs the What.
The How. By removing consulting as an option, I streamlined three delivery-types into two, writing and speaking. Each of which have several offerings nested underneath. All of which relate to communication.
Facilitation and leading workshops? Communication
Narrating an online course? Communication
Drafting a change management strategy? Communication
In my case, testing out a variety of delivery types helped to reshape what I offered.
It brought clarity and removed the kind of work I was ill-suited for at this point in my career. I genuinely feel that trying out a variety of delivery types, and being open to offers that fall outside of those is a great experience early on. In doing so, it is imperative to keep records and build a big enough sample of work experiences to reflect on.
How else will you know if you really enjoy a specific type of client engagement? A handful of positive or negative experiences aren’t enough data points to reach a conclusive decision.
The mindset of an employee is to take on everything, and that is likely where you will start off too. The mindset of a business owner slowly morphs into recognizing you won’t be great at everything you try. That some types of work aren’t right for you, or aren’t right for you at this time.
The odds of you nailing What You Do and How You Do It perfectly on the first try are incredibly slim. Don’t set yourself up for failure with a rigid approach to either.
Experimentation opens doors. Record keeping, reflection and a new mindset allows you to close some.
Keep Reading: the second part of this series looks at the hidden costs of working for yourself.
