Why I’m Seeing a Financial Planner and Sticking With It

So, I started seeing someone. And I think it has long-term potential.

You know how sometimes you just know? We were introduced by a mutual friend, and I trusted him immediately. During our first meeting, I revealed more than I expected — about who I am, what I want, my hopes and fears for the future. I liked his silver hair, his big grey eyes, his quick, slightly self-deprecating manner. 

What can I say? He listened to me. He really cared. He said he was impressed by me, but could see I needed a bit more structure in my life, and some support wouldn’t hurt. He was right. After knowing me for less than two hours, he said that he could see us together for the next 20 years. I’m not kidding. When I walked home that evening, I was … buoyant. Optimistic. And most importantly, I felt empowered.

Did I mention he’s in a relationship? Oh, and he’s gay, too. But that’s fine. I’m just using him for his money… advice. Yes. He’s my new financial planner. 

Oh, there’ve been others, sure. Years ago, a guy who promised me the moon, then had some kind of breakdown and changed careers. Then there was Dana, who I loved, but I moved away and our lives went in different directions. 

But Michael is different. He’s here to stay. No, this is not a story about a damsel in distress who can’t figure it out and needs a man to do it for her. That story’s played. But as with any relationship — romantic, familial, platonic — the best ones are partnerships. The other person supports your weaknesses and highlight your strengths. 

I’ve been working as a solopreneur for two years. I’m proud of what I’ve done in that time: reinvented my personal brand, established solid working relationships with trusted clients, expanded my skill set. Got a few new professional notches on the old belt. But I haven’t been doing much with my money except spending some, while saving a bunch in a digital pocket to hand over to Uncle Sam.

I’ve had great months and not-so-great months, and my excuse for staying low to the ground and light on my feet financially was that I should just keep everything liquid and accessible.  Why? Because, “Hey, I’m new to this!” and “I don’t know where money’s coming from next so better keep it handy right here in my mattress!” 

That isn’t going to cut it anymore.

I’ve realized, yeah, I’ll never know where money is coming from or what things could shift and leave me high on the hog or fidgeting in the red. But to do nothing about it is like hoping it rains the next time you’re thirsty. If you want water on hand, you have to have a system in place to collect it for when you inevitably do want it, not assume because it’s raining it’s going to keep raining. And I’ve had some very dry seasons. 

Leaving my full-time job and going rogue was the biggest adventure ever. And as with all adventures, you’re 100 percent focused on just being able to do it. To survive. So, I got quite used to what amounted to the financial equivalent of camping: got my fire, my pot, my can of beans and a place to lay my head. Why would I need to worry about blueprints for a house? Ah, because camping is fun for a bit, but soon you’re going to want to come indoors. 

In this sense, a full-time job will keep you honest — you opt in to systems that auto-filter your income into medical, dental, 401(k). And while I have insurance covered (thanks, Freelancers Union!), I wasn’t doing much saving for the future because it didn’t seem as relevant or urgent (does it ever?). 

But at play here was another fear: fear of settling down. I resisted putting structures in place because it would mean locking down my freedom, doing away with the fun part of being free of full-time employment. Plus, settling down looks a certain way: house, car, kids — things that are not on my bucket list. And so I was using that excuse (“Not me!”) as a reason to keep all the money in my pocket. But I was increasingly aware that my little tent would not likely hold in a storm. 

Plus, I’m not a kid anymore. And what’s really not fun is to live hand-to-mouth and think this is how it will always be. As Kate Bolick said in her much-buzzed-about Atlantic piece in 2011 (“All the Single Ladies”), “If I stopped seeing my present life as provisional, perhaps I’d be a little … happier.”

“I’m not going to retire, either,” I bragged to Michael. “So I don’t need to save for that.” Michael then gently reminded me that while I might always want to work, I might not always have the same opportunities to do so. Just the way of the world. “Let’s not think of it as ‘retirement.’ Let’s think of it as lifestyle.” 

Aha. Now he was speaking my language. Because planning for retirement is planning for the end of things (productivity, relevance, opportunity). So it’s no wonder that the traditional “save for retirement” spiel never worked on me. When anyone has ever tried to use that rationale, they might as well have handed me a shovel and told me to start digging my own grave. I would rather spend money on a beautiful bookshelf now than save it for 30 years down the road when I need one of those chairs that zips you up the stairs. 

Lifestyle extension, however. That made sense to me. This isn’t about giving in to the “end” as much as it is ensuring that I can live the life I want for longer. 

And just as I have no interest in hanging my own cupboards, I also don’t need to know how to set up a SEP IRA account. And that’s where I’m grateful to Michael — because I believe that even the best and brightest among us don’t do anything without the help of someone else. 

Yet the real reason I was bouncing down the sidewalk on my way home after meeting Michael that night was because of a powerful shift that woke me up to my own agency. It’s as if I looked down and saw I was wearing a pair of ruby slippers all along. Michael didn’t give them to me. But he does know just what I should wear with them. 

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