Wisdom for Freelancers and Lovers
The beginning of my freelance business came on the heels of an extended period of learning about how to be a good adult to the important people in my life. It turns out that learnings from my personal life ended up helping me run my consulting business.
Good people and good business
My 20’s saw a series of relationships go the route of so many careers of musical one-hit-wonders: incredibly exciting for a summer or so, and then disappearing without much of a trace within a few months. Eventually I owned up to the fact that I was the common factor in all of these situations, and I started a learning project for myself focused on the basics of being good to other people: communicating effectively, authentically being generous, and setting boundaries. To my surprise, the lessons I learned during this time didn’t just impact my personal life; they have ended up having a major impact on me as an entrepreneur and freelancer as well.
I’ve been thinking a lot about these lessons as I dive deeper into my some personal and professional relationships, and decided to write them down so that I could return to them from time to time.
In short, three things I learned about personal relationships that have made me better at business:
- This is a process. Don’t rush it. Every step is a milestone.
- Be honest, with others and yourself, about what you’re offering.
- Make room for mistakes, breaks, and next takes.
Lesson 1: This is a process. Don’t rush it. Every step is a milestone.
Two years ago, I left a corporate job and started freelancing. It was a process that felt a lot like breaking up with someone then (after a short break) getting back into dating: there was a desperation to meet people and, as soon as possible, feel the same sense of security or validation I had in my previous arrangement. Once I started freelancing seriously, I developed a work mentality akin to something out of trap music anthem: hustle hard, stack cash fast, and then …. repeat? (what is the endgame in all those songs, anyway?)
I quickly got to a point where I had work to fill my time, but the feeling I got from doing this work wasn’t a lot better than the feeling I had when I had decided to leave my previous job. Working for myself was supposed to be different, but something was off.
In my personal life at the time, I was learning about the importance of intention and embracing process. This led me to ask “why?” a lot more: Why do I pursue innumerable social commitments when I want to focus on my professional and spiritual life? Why do I maintain relationships that feel “heavy” and full of friction? Why do I go to the club when it’s often expensive, uncomfortable and boring?
Often times, the answers came down to insecurity, habit, or just not taking the time to be clear about my goals and what it would take to achieve them.
Out of this personal practice of asking why more often, two deceptively simple practices emerged for me:
- State — clearly and deeply, sometimes in short memos — why I am doing the things that take a lot of my time or energy.
- Focus my time and energy on meaningful processes — not just outcomes. Outcomes are often fleeting, and not more meaningful than journeys. Live a little purpose every single day.
Socially, this led to a renewed interest in finding creative ways to show up for close friends, instead of just attending exciting-sounding events with lots of people. It also led to trying to understand what I wanted from a relationship, instead of just wanting to be “in” a relationship.
Applying these lessons to my work life meant taking a step back and boldly, fearlessly thinking about what I wanted my business to look like, act like, *be* like.
Whereas I once primarily thought about running a business that managed to be financially stable, asking why pushed my thoughts beyond financial sustainability.
I realized I wanted to:
- Work with awesome people I’d be glad to call friends
- Constantly be learning new skills and perspectives
- Do work that was making the world a more compassionate, inclusive, just place
This sounded like job utopia when I wrote it out. But, at some point I figured if life is a journey (with an end) anyway, might as well be on a journey towards something awesome.
Once I wrote this list down, I realized my previous work mentality came from a place of wanting immediate validation in the form of job prestige or an ever-increasing salary. Success by my new definition wasn’t going to come as quickly or easily as a paycheck. So, I started focusing on how I endure for the long road toward my ideal job, instead of trying to rush through hard hustles and fast cash. This didn’t preclude a desire to make money — those bills don’t pay themselves — but it did involve seeing this short-term money making as a part of a larger purpose project of doing something that meant something.
Lesson 2. Be honest, with others and yourself, about what you’re offering
I’m a stereotypical overachiever, so I continue to struggle with two tendencies: the desire please others, and the belief that I can do anything. In moderation, these can lead to being helpful and ambitious; in excess, they can lead to insecurity, burn-out, and the souring of friendships and romance.
This has been a big point of growth for me in my romantic relationships. I once felt that I had to promise someone the moon and the stars in order for them to be interested in me. Initially, this brought a lot of enthusiasm from the person I was dating. However, I would quickly feel out of place in these situations because I felt like I was being held to expectations that didn’t reflect who I was or what I wanted. In a rush to get romantic validation from a prospective partner, I hadn’t adequately considered what I was excited to give or what I needed out of the relationship. In the end, this resulted in me being unsatisfied, the person I was dating being confused, and the two of us falling apart.
The key to fixing this came to check-ins, the power of needs, and a little faith. First, I needed to learn to check-in with myself at points to understand what I was capable of and excited about. When I was in the last 6 months of graduate school for example, I realized that dating probably would not be my top priority — and I had to own that. Second, I needed to affirm that my goal was to meet my partner’s needs and my own needs — not just get validation or boost my ego. When you’re focused on meeting needs in a relationship, your actions end up being more directed, informed, and sensible. You also end up sharing more vulnerably — it turns out hiding what we deeply need is a prime strategy for keeping people from understanding who we really are. Third, I needed to have faith that if one of us couldn’t meet the other’s needs, it wasn’t the end of the world. The appropriate action in this case was to try to work towards alignment (if that made sense), or end the partnership.
Solidifying these three points in my personal life led to some transformative changes in business relationships, too. At one point this year, working with one of my clients started to feel burdensome and unmotivating. After struggling with this for months, I realized that I was primarily doing this work to make myself feel good — I didn’t have the attention or bandwidth to really meet their needs. Bringing this up spurred a conversation that totally turned around the nature of our partnership for the better.
With more reflection, I’ve realized that ego or a feeling of desperation can influence me to take on clients; but, these should never be the deciding factors in who I work with. When I start to feel these tugging, I need to check-in with myself about what kind of work I want to be doing, and be as honest as possible with my clients about my needs and preferences. If there’s synergy between the client and me, great. If not, I need to have the faith to move forward in a way that makes sense for both of us.
The perspective that this point has given me for my business life is:
- I should take stock of the work that I’m excited to be doing, the ways I can bring value, and what I’m interested in learning. I should also reflect on the type of work I’ve done that I’d rather not do again. I should take jobs that give me a chance to do what I want; don’t take jobs that require me to do what I don’t want — without some sort of benefit.
- I should take time to articulate a vision and mission for myself as a freelancer — this isn’t just something for large businesses. Seek jobs that are in alignment with these two things.
- I should take on jobs where the client and I have an ability to meet each others deep needs; not just superficial needs.
Not every partnership that makes itself available for me is right for me — even if it seems lucrative or highly-visible. I have a better chance of finding a good match if I am enthusiastic and confident about giving what a business partner needs.
3. Make room for mistakes, breaks, and next takes
Starting a business on my own felt like jumping into a rushing river after taking only one swim lesson: I knew the basics, and for some reason I thought I could learn the rest while being hurled forward by chaos. To endure as an entrepreneur without being in a constant state of crisis, I’ve had to think differently about “achievement” than I once did: I’ve had to figure out how to fail, rest, and do better graciously even when it feels like the stakes are very high.
I’ve been bad at a lot of things in my life. In middle school, I spent a season on the track team where I came in last in every single race. But, I had a perspective about this: it’s okay to be bad at things that don’t matter (for me, sports), but I had to be good at the important stuff (work, money, and relationships). The problem with this mentality is that we’re usually bad at anything that’s truly new — even if it’s important. Sometimes, we’re bad even when we’ve been doing something for a while. My fear of appearing bad at some important things made me anxious, prone to over compensation, and hesitant to try.
In my personal relationships, I’ve been guilty of expecting too much from myself and others. I have had friendships and romantic relationships collapse because:
- I’ve expected to get support from people while, at the same time, hiding that I needed it
- I’ve wanted friends to show up for me when they were feeling overburdened in their own life
- I felt bad that I wasn’t able to make other people feel valued or supported, even as they took active steps to create space between us, so I initiated an end
- I didn’t imagine that I could be forgiven for making a decision I later regretted, so I distanced myself
These expectations have a consistency: when I have unreasonable expectations for myself, I also end up having them for other people.
Two things have helped me to shift to a mindset more tolerant of imperfection: having friends who stood by me at my most challenging, vulnerable and “weakest” moments, and therapy sessions that reinforced my worth beyond my ability to look good for others. I’m now at a place where I feel more comfortable — within myself — making mistakes, learning from my mistakes, and trying things again. Not only do I feel more comfortable doing these things, I feel more comfortable requiring that — as an imperfect human who is constantly trying new things — I be allowed to go through this process with other people. Especially for the important things.
In my business life, I’ve been working to apply this “mistakes, breaks, and second takes” framework as a core practice of how I do business. I’ve engaged with clients where I held myself to an unreasonable standard, didn’t communicate when I faced challenges, and had projects go poorly. For me, the solution to this lies in the ability to:
- Place humility over ego, and admit that we all need extra help or time sometimes
- See ourselves as in the process of growing, so being transparent about growth moments
- Center the business process on mutually meeting your needs and your client’s needs, and updating the relationship if your need for growth doesn’t meet your client’s need for performance (see the previous tip).
This has been the trickiest of the lessons for me to apply; I’m still working on making this a part of how I work. Towards this goal, I’m practicing three surprisingly tough phrases:
- “I don’t know but I can try to learn”
- “I’m not sure I can, but I can try”
- “I’m sorry. I’ll work to do better next time”
Fin
As I move forward with my business development, I’m trying to develop a philosophy and practice of how I engage — and these three lessons are becoming tenants of that.
For more information on some communication techniques, I highly recommend the Principles of Non-Violent communication.
