Career - Finding career guidance

There are many different facets of seeking career advice. It’s an all-encompassing topic because a person’s career is interwoven with their life. See the sample list that follows:

Determining goals
Managing the work-life balance
Recognizing signs of burnout
Identifying strengths and doubling down on them
Identifying weaknesses and improving at them
Managing imposter syndrome
Identifying opportunities for growth
Understanding when to ask for help
Understanding when to escalate a situation and when to ignore
Determining optimal working environments and team size
Navigating job changes

Determine where you want to go #

The first thing you need to do is determine where you want to go. Nobody can guide you if you don’t know the general direction you would like to head. Given you’re reading this article, it’s probably fair you intend to be involved in software engineering in some way. That’s a great start.

The next thing I’d suggest is reviewing where you want to be in 10 years. This should cover your personal life, career, family, pretty much everything. Consider what types of responsibilities you want, how you hope to spend your time, and what you aim to be capable of.

Keep in mind that this is general direction setting. The point isn’t to treat this as a checklist but as an exercise in self-planning. Doing a bit of self-reflection to determine what your priorities are right now will help you be flexible when assessing future opportunities.

Now that you’re armed with a general direction, you can start seeking out additional help.

Finding career guidance from friends and family #

The benefit of asking friends and family is that they are intimately aware of who you are. They have plenty of context around you and your life. This means it takes less time for you to get the person to understand where you’re coming from. The shared history allows them to empathize with you more deeply, allowing them to provide better advice.

The concerns are twofold. The first is, do they have enough context and experience in software engineering to provide specific career advice? Not everyone is in software engineering, or engineering, or even a technical field. While it’s great to have an outside perspective, many questions require insider knowledge. The second concern is, is the person able to see past their biases and shared history with you? It can be difficult for people to set aside who you used to be and see you for who you are now.

Just having these conversations can change the relationship. If there is a debt between friends, in either direction, and you mention that you’re considering starting your own business, that friend will inevitably think that the debt needs to be repaid soon. That may impact how they see your endeavor, the advice they give, and how they think of your relationship. For example, if someone helped you get your job, taking another may impact them. Recognizing these dynamics before the conversation allows you to choose the right person, be intentional about what you’re revealing, and be clear about what kind of support you’re actually looking for.

Another thing to keep in mind is that sometimes you want to keep your professional and work lives separate. Using time with your loved ones to process career challenges may take away from the relationship. Some relationships will thrive with these types of topics, and others may be drained.

Despite the challenges, advice from family and friends is incredibly valuable. Their knowledge of your core values and ability to trace decisions back to those values can be immensely reassuring.

Finding career guidance from colleagues #

There is plenty of guidance to be found from your colleagues because it’s such a diverse and wide group of people. I’m lumping everyone in this category who qualifies as an acquaintance that you know for professional purposes. This includes all of your work colleagues, the people in your Discord servers, your conference pals, and fellow community members.

That diversity of thought is bound to contain valuable information for you. The breadth of the sum of knowledge is incredibly large. Their combined lived experience is immeasurably vast. It’s actually kind of cool to consider you have access to all of this information and resources.

Someone in your network is likely to have already experienced something that you’re facing now. You can use that as a resource to guide you on your journey!

The challenge here is finding the opportunity to receive the guidance.

It’s a logistics problem. If a topic is sensitive or nuanced, you can’t broadcast that you’re looking for help on it. Not many people are broadcasting, “I feel overwhelmed by our industry and my job; how do I manage this!?” Which is a healthy discussion topic, but asking that question at work can cause others to look at you differently. The more sensitive a topic is, the more we rely on our trusted connections, which dramatically shrinks that diverse pool of experience we had access to. So maybe instead of thousands of people, we only have dozens. And even then, how do you communicate with each of them individually? It’s quite the conundrum.

The solutions I’ve used here are to find safe spaces to regularly participate in¹, be bolder in asking questions and talking about experiences, and purposefully grow my network.

Smaller communities that operate with a FriendDA-type agreement. Conference Chats is an example of a niche community that provides high-quality guidance regarding running conferences. Once you find these communities and regularly participate, you need to actually tell people you’re looking for guidance. This is where the boldness factors in. Unsurprisingly, people are more likely to share their experience when you tell them you’d like to hear it.

Some people maintain connections in their network naturally. Others, like myself, need to dedicate conscious effort towards it. This is one of those “if it’s uncomfortable for you, it means you’re growing” type of things. If you’re looking for a specific process, Jay Miller has an excellent article. Otherwise, my general advice is to periodically send messages of gratitude to others, schedule recurring meetings with people, and engage with people that seem interesting.

Growing your network, including your inner circle, can help you solve a number of future problems. It’s not something that can be done instantaneously and takes time to cultivate, so it’s best to start soon.

Finding career guidance from content #

Finding career guidance from content is great because it’s fairly accessible. You can access it today! There’s plenty of content that exists out there. There are books, articles, podcasts, videos, conference talks, chat servers, Reddit, Hacker News, and even LLMs that can be a source of guidance.

This guidance is great because it’s written to be informative and understandable. You may even be able to find very specific niche content.

For example, the podcast “Soft Skills Engineering” allows people to write in with their question, and their response is the show. The question asker can provide as much context as they want, though it’s typically a few sentences. It is a show after all. For the question asker, that content is precisely what they were looking for.

There are some obvious challenges with getting career guidance from content. Challenge number one is that content can’t understand the full context of your situation. Content is unidirectional. Books, blogs, podcasts and videos speak at you. There are places for comments, but as the content becomes more popular the more unlikely it is that the author will have time to chat with everyone.

Challenge number two: you don’t know what experiences lead to generating the advice (see “Consider the source of advice”). Some pieces of advice are generalized and don’t provide a ton of context around why it’s important. Which makes sense. A lot of background information is required properly convey the full context of a situation. As that context diverges from your own, you as a reader become less interested in it reducing it to noise. The creator’s challenge is balancing providing context with providing the useful advice. Your challenge is using that context to determine how applicable the advice is to you.

The last challenge is simply finding the context. It can be difficult to find quality posts on career guidance. Some of my favorite resources are Jacob Kaplan-Moss’ blog, “Soft Skills Engineering”, so many books², this article on salary negotiation by patio11/Patrick McKenzie and the Django News newsletter.

One technique that is effective in finding new content is to ask your existing network what their favorite resources are. When people have content they enjoy, they want to share it with other people (see previous paragraph). A nice side benefit is that this is a great way to start building your network too. This gives you several small entry points to creating acquaintances that you can rely on in the future.

While not completely built out yet, I am working on adding content to this site. I would like to provide a curated collection of resources to help guide people to helpful content that is relevant to their situation. If this is of interest to you, please consider subscribing.

Choosing where to find guidance #

When you are in need of guidance that requires a strong understanding of your values, character and personal story, you should rely on friends and family. They have a deep connection with you which grants them a unique perspective.

When you are in need of guidance that is less centered on you and can benefit from a wider range of opinions, you should ask your colleagues. In these situations you’re asking them to share their experience, so it’s on you to determine if it applies to you. If the situation requires a high level of context, this may not be a good option. However, having a broad set of opinions to determine if something is normal is truly useful.

When you need to discover what options are available, that’s when you should rely on content. Content is excellent at providing ideas and concepts that are beyond your circles. This is also where the sources work together; your colleagues, friends and family can help you evaluate whether content is credible and relevant to your situation.

Jeff Triplett’s office hours are a great example. ↩
I’m working on creating a section of book reports to help direct people to quality resources. ↩