Rambling Man: Help! I’m Consumed By Worry That I’m A Failure

by Joshua Michtom

Dear Rambling Man,

I am a 30 year old female person, living in Washington DC. I am married, and my husband and I recently bought a house. Kids are in the near to medium term future (we hope!). I also have a job that I hate. The work itself is fine, if not super interesting or engaging, and I have been in the job for a year and a half. I make an OK salary, and have health insurance and the other safety nets that come from a salaried position. But the environment in my office is very close to toxic on most days and there has been a clear indication that promotion is not in the cards. I have been described by the (female) president of our group as all the things women don’t want to (shouldn’t have to) hear about themselves in a work situation: overly ambitious, too confident, too outspoken, etc. I’ve received little to no support from the others in my group who recognize that these are unfair characterizations, or at least not productive ones.

Knowing this, I started looking for a new job, and quickly found one that is a departure from my current work. I would be moving from government relations to grant writing/non-profit management. The new job has a salary about 5% lower than my current salary, but I’ve been told I will be promoted and given a significant (15–20%) raise within 6 months once I learn the ropes. My husband and I have very little debt (except the mortgage) and are doing FINE financially. My pay cut and his COLA this year would make the short-term transition essentially a wash. He is fine with this, and it’s totally doable.

Now to my problem. I am worried that taking this new job somehow means I failed because it’s not what I set out to do. I thought I wanted to do the DC thing and go to fancy cocktail parties in a pantsuit and write/think about important things (ugh). If I take this new job, am I giving that image of myself up? Eventually, this could lead me into a position of leadership or development in a non-profit, which is something I think I could love and be really good at. But for now, I am consumed by worry that I am a failure, and that I am doomed to not ever like or be successful because I have changed jobs several times in the last 5 years. Help.




Dear Confused,

It occurs to me that commenters might be tempted to dismiss this issue out of hand, perhaps with the ever-popular hashtag “#firstworldproblems.” I do not think that is appropriate. Yes, you will probably be OK no matter what. And yes, for many among us, a life of glamorous pantsuit soirees doesn’t seem to present any competition to a happy work life bolstered by a happy and financially secure home life. But disappointment can be a corrosive thing and it has to be addressed on its own terms.

For example, all I can think lately is, “Why couldn’t Lucas Duda just make that goddamn throw to retire Hosmer at home plate and win the game?” It’s no use for people to say, “Hey, the Mets had a great run and no one expected them to win their division, let alone the league championship.” It would be even worse for people to say, “Professional baseball is an atrocity,” even though both of those things are true.

So I’m going to proceed on the assumption that this is a real dilemma that presents the real possibility of ongoing, joy-sapping regret.

I do not know you, so I cannot say with any certainty whether these glamorous pantsuit gatherings are worth it. People have different values. I can tell you this: for as long as I can remember, even before I had any interest in becoming a lawyer, I thought that lawyers who represented poor people were the greatest, and that to achieve their position, learned but humble, imbued with a specialized skill perfectly designed to help others while providing you with a living, was to arrive at the maximum expression of successful adulthood.

Then, when I became such a lawyer, I found out that one of the consequences of getting an expensive education to do a job that pays poorly and demands huge chunks of your soul is that success can seldom come without sacrifices in other areas of endeavor. Put more bluntly, the first public defender office I worked in was an efficient factory of alcoholism and divorce.

Now, that’s not to say that the whole world is like “Something Wicked This Way Comes,” where you’d only get your wish to go to pantsuit parties if you lost both legs in a horrible Presidential motorcade-induced pile-up. But it is surely true that the lives we dream of living and the identities we hope to grow into don’t always work out as we’d expected. On NPR the other evening (because I am a person who listens to goddamn NPR while driving in his goddamn Prius, which means I have managed to embody something I emphatically did not set out to become), they were talking about this documentary on the famous diplomat, Richard Holbrooke, made by his son, David Holbrooke.

Richard Holbrooke definitely did live that DC-fancy-people life, although perhaps not in a pantsuit, and is much admired for all the peace-brokering he did. But the NPR segment was bittersweet: the son talked about how absent his father was and how the documentary was a way to make peace with that. He emphasized that, by learning that his father was absent for a good cause (ending wars, etc.), he was able, eventually, to feel OK about that absence.

I’m glad the son found this peace, but the process makes a point: doing the great things doesn’t insulate people from the lousy things.

I don’t mean that brokering historic Balkan peace accords necessarily requires familial estrangement, just as entree to the world of pantsuit parties doesn’t necessarily require a toxic work environment, and defending people’s constitutional rights doesn’t necessarily lead to adultery, substance abuse, and crushing loneliness. But it is seldom the case that our dreams come without drawbacks. Recognizing and weighing drawbacks we didn’t know about doesn’t make us failures; it makes us successful. There is value in dogged determination to see something to its conclusion. But not every lousy career needs to be pursued miserably until retirement, nor every unhappy marriage stoically and sexlessly endured into a bitter, clenched-denture, elderly détente.

Take the new job. Go with your husband to that noodle place on H Street where you have to wait like two hours for a table. After you put your name in, get drinks at the Belgian bar down the street so you are a bit tipsy by the time they text you to say your table is ready. Order expensive drinks with your fancy noodles. Enjoy glamor without pantsuits.

Rambling Man is the Billfold’s new advice column about trying to make a living and doing the best you can. Questions for Rambling Man? Email ester@thebillfold.com, subject line: Rambling Man.